NCERT CBSE Standard 12 Haloalkanes and HaloArenes Chapter 10 Organic Chemistry SKMClasses South Bangalore Subhashish Sir

Chapter 10 :

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10.1 Haloalkanes and Haloarenes

10.1-1 Ans Haloalkanes

10.1-4,5 Ans Haloalkanes

10.1-6,7 Ans Haloalkanes

10.1-8,9 Ans Haloalkanes

10.1-10,11 Ans Haloalkanes

10.1-12 Ans Haloalkanes

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Untitled

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1 Periodic trend in Electrode potential-4

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10.2 Haloalkanes and Haloarenes

10.2-1,3 Ans Haloalkanes

10.2-4,5 Ans Haloalkanes

10.2-6 Ans Haloalkanes

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10.3 Haloalkanes and Haloarenes

10.3-1,3 Ans Haloalkanes

10.3-4,6 Ans Haloalkanes

10.3-7,8 Ans Haloalkanes

10.4 Haloalkanes and Haloarenes

Ans : The dipole moments are calculated as follows

10.4-1 Ans Haloalkanes

10.4-2 Ans Haloalkanes

10.5 Haloalkanes and Haloarenes

Answer :

10.5-1 Ans Haloalkanes

10.6 Write the isomers of the compound having formula C4H9Br.

Ans :

10.6 Ans Haloalkanes

2-Bromo-2-methylpropane

10.7 Write the equations for the preparation of 1-iodobutane from
(i) 1-butanol  (ii) 1-chlorobutane (iii) but-1-ene.

10.7 Ans Haloalkanes

10.8 What are ambident nucleophiles? Explain with an example.

10.8 Ans Ambidentate Nuleophile
10.9 Which compound in each of the following pairs will react faster in SN2 reaction
with –OH?
(i) CH3Br or CH3I (ii) (CH3)3CCl or CH3Cl

10.9 Ans SN2 reaction speed

10.10 Predict all the alkenes that would be formed by dehydrohalogenation of the
following halides with sodium ethoxide in ethanol and identify the major alkene:
(i) 1-Bromo-1-methylcyclohexane

10.10-1 Ans Haloalkanes

(ii) 2-Chloro-2-methylbutane

10.10-2 Ans Haloalkanes
(iii) 2,2,3-Trimethyl-3-bromopentane.

10.10-3-1 Ans Haloalkanes

reaction

!
10.11 How will you bring about the following conversions?
(i) Ethanol to but-1-yne

10.11-1 Ans Haloalkanes

(ii) Ethane to bromoethene

10.11-2 Ans Haloalkanes

(iii) Propene to 1-nitropropane

10.11-3  Ans Haloalkanes

(iv) Toluene to benzyl alcohol

10.11-4  Ans Haloalkanes

(v) Propene to propyne

10.11-5  Ans Haloalkanes
(vi) Ethanol to ethyl fluoride

10.11-6  Ans Haloalkanes

(vii) Bromomethane to propanone

10.11-7  Ans Haloalkanes

(viii) But-1-ene to but-2-ene

10.11-8  Ans Haloalkanes

(ix) 1-Chlorobutane to n-octane

10.11-9  Ans Haloalkanes

(x) Benzene to biphenyl

10.11-10 Ans Haloalkanes
10.12 Explain why
(i) the dipole moment of chlorobenzene is lower than that of cyclohexyl chloride?

Ans :

10.12-1 Ans Haloalkanes

!
(ii) alkyl halides, though polar, are immiscible with water?

Ans :

10.12-2 Ans Haloalkanes

!
(iii) Grignard reagents should be prepared under anhydrous conditions?

Ans :

10.12-3  Ans Haloalkanes

10.13 Give the uses of freon 12, DDT, carbon tetrachloride and iodoform

Ans :

10.13  Ans Haloalkanes

10.14 Haloalkenes

10.14  Ans Haloalkanes

10.14-2  Ans Haloalkanes

10.15 Haloalkenes

Ans :

10.15  Ans Haloalkanes

10.16 Haloalkenes 10.16-2 Haloalkenes

Ans :

10.16-1  Ans Haloalkanes

10.16-2  Ans Haloalkanes

10.16-3  Ans Haloalkanes

10.17 Haloalkenes

10.17  Ans Haloalkanes

10.18 p-Dichlorobenzene has higher m.p. and solubility than those of o- and m-isomers.
Discuss.

Ans :

10.18  Ans Haloalkanes

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7 Mach naki fish 3 Mistry sculpture 5 Kather hanti 6 Jol dhalar jog

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10.19 How the following conversions can be carried out?
(i) Propene to propan-1-ol

Ans :

10.19-1 Ans Haloalkanes
(ii) Ethanol to but-1-yne

10.19-2 Ans Haloalkanes
(iii) 1-Bromopropane to 2-bromopropane

10.19-3 Ans Haloalkanes
(iv) Toluene to benzyl alcohol

10.19-4 Ans Haloalkanes
(v) Benzene to 4-bromonitrobenzene

10.19-5  Ans Haloalkanes
(vi) Benzyl alcohol to 2-phenylethanoic acid

10.19-6  Ans Haloalkanes
(vii) Ethanol to propanenitrile

10.19-7  Ans Haloalkanes
(viii) Aniline to chlorobenzene

10.19-8  Ans Haloalkanes
(ix) 2-Chlorobutane to 3, 4-dimethylhexane

10.19-9  Ans Haloalkanes
(x) 2-Methyl-1-propene to 2-chloro-2-methylpropane

10.19-10  Ans Haloalkanes
(xi) Ethyl chloride to propanoic acid

10.19-11  Ans Haloalkanes
(xii) But-1-ene to n-butyliodide

10.19-12  Ans Haloalkanes
(xiii) 2-Chloropropane to 1-propanol

10.19-13  Ans Haloalkanes
(xiv) Isopropyl alcohol to iodoform

10.19-14  Ans Haloalkanes
(xv) Chlorobenzene to p-nitrophenol

10.19-15  Ans Haloalkanes
(xvi) 2-Bromopropane to 1-bromopropane

10.19-16  Ans Haloalkanes
(xvii) Chloroethane to butane

10.19-17  Ans Haloalkanes
(xviii) Benzene to diphenyl

Biphenyl

Benzene to biphenyl-1

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4 Hantir opore

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Option -1:

Treat benzene with oleum then treat product with sodium hydroxide and an acid then you can get phenol treat it with zinc chloride then you can have chloro benzene treat it with sodium in dry ether ” fittig reaction ” then you can have di phenyl

Option -2:

1) do nitration and convert benzene to nitro-benzene.2) treat it with 3 H2 and you’ll get Aniline. 3) treat Aniline with HONO/ conc. HCl and you’ll get benzene Di azonium chloride. (C6H5 -N2Cl)4) Now again treat it with benzene you’ll get Di- phenyl.(4)step is called Gambhar reaction.)

About Biphenyl -

Biphenyl (or diphenyl or phenylbenzene or 1,1′-biphenyl or lemonene) is an organic compound that forms colorless crystals. It has a distinctively pleasant smell. Biphenyl is an aromatic hydrocarbon with a molecular formula (C6H5)2. It is notable as a starting material for the production of polychlorinated biphenyls (PCBs), which were once widely used as dielectric fluids and heat transfer agents. Biphenyl is also an intermediate for the production of a host of other organic compounds such as emulsifiers, optical brighteners, crop protection products, and plastics. Biphenyl is insoluble in water, but soluble in typical organic solvents. The biphenyl molecule consists of two connected phenyl rings.

Biphenyl is produced industrially as a byproduct of the dealkylation of toluene to produce benzene :

C6H5CH3 + C6H6 → C6H5-C6H5 + CH4

The other principal route is by the oxidative dehydrogenation of benzene

2 C6H6 + 1/2 O2 → C6H5-C6H5 + H2O

(xix) tert-Butyl bromide to isobutyl bromide

Tert Butyl Bromide to Isobutyl Bromide
(xx) Aniline to phenylisocyanide

Aniline to phenyl isocyanide

10.20 The treatment of alkyl chlorides with aqueous KOH leads to the formation of
alcohols but in the presence of alcoholic KOH, alkenes are major products. Explain.

Ans :

10.20  Ans Haloalkanes

10.21 Primary alkyl halide C4H9Br (a) reacted with alcoholic KOH to give compound (b).
Compound (b) is reacted with HBr to give (c) which is an isomer of (a). When
(a) is reacted with sodium metal it gives compound (d), C8H18 which is different
from the compound formed when n-butyl bromide is reacted with sodium.
Give the structural formula of (a) and write the equations for all the reactions.

10.21-1  Ans Haloalkanes 10.21-2  Ans Haloalkanes

10.22 What happens when
(i) n-butyl chloride is treated with alcoholic KOH,

Ans :

10.22-1  Ans Haloalkanes
(ii) bromobenzene is treated with Mg in the presence of dry ether,

10.22-2  Ans Haloalkanes
(iii) chlorobenzene is subjected to hydrolysis

10.22-3  Ans Haloalkanes
(iv) ethyl chloride is treated with aqueous KOH

10.22-4  Ans Haloalkanes

!
(v) methyl bromide is treated with sodium in the presence of dry ether

10.22-5  Ans Haloalkanes

!
(vi) methyl chloride is treated with KCN?

10.22-6  Ans Haloalkanes

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Halogenated compounds persist in the environment due to their resistance to breakdown by soil bacteria.

The replacement of hydrogen atom(s) in a hydrocarbon, aliphatic or aromatic, by halogen atom(s) results in the formation of alkyl halide (haloalkane) and aryl halide (haloarene), respectively. Haloalkanes contain halogen atom(s) attached to the sp3 hybridised carbon atom of an alkyl group whereas haloarenes contain halogen atom(s) attached to sp2 hybridised carbon atom(s) of an aryl group. Many halogen containing organic compounds occur in nature and some of these are clinically useful. These classes of compounds find wide applications in industry as well as in day-to-day life. They are used as solvents for relatively non-polar compounds and as starting materials for the synthesis of wide range of organic compounds. Chlorine containing antibiotic, chloramphenicol, produced by soil microorganisms is very effective for the treatment of typhoid fever.Our body produces iodine containing hormone, thyroxine, the deficiency of which causes a disease called goiter. Synthetic halogen compounds, viz. chloroquine is used for the treatment of malaria; halothane is used as an anaesthetic during surgery. Certain fully fluorinated compounds are being considered as potential blood substitutes in surgery.
In this Unit, you will study the important methods of preparation, physical and chemical properties and uses of organohalogen compounds.

10.1 Classification
Haloalkanes and haloarenes may be classified as follows:

10.1.1 On the Basis of Number of halogen Atoms

On the These may be classified as mono, di, or polyhalogen (tri-,tetra-, etc.) compounds depending on whether they contain one, two or more halogen atoms in their structures. For example,

Monohalocompounds may further be classified according to the hybridisation of the carbon atom to which the halogen is bonded, as discussed below.

10.1.2 Compounds Containing sp3 C—X Bond (X= F, Cl, Br, I)

This class includes
(a) Alkyl halides or haloalkanes (R—X)

In alkyl halides, the halogen atom is bonded to an alkyl group (R). They form a homologous series represented by CnH2n+1X. They are further classified as primary, secondary or tertiary according to the nature of carbon to which halogen is attached.

(b) Allylic halides

These are the compounds in which the halogen atom is bonded to an sp3-hybridised carbon atom next to carbon-carbon double bond (C=C) i.e. to an allylic carbon.

(c) Benzylic halides

These are the compounds in which the halogen atom is bonded to an sp3-hybridised carbon atom next to an aromatic ring.

10.1.3 Compounds Containing sp2 C—X Bond
This class includes:

(a) Vinylic halides

These are the compounds in which the halogen atom is bonded to an sp2-hybridised carbon atom of a carbon-carbon double bond = C).

(b) Aryl halides

These are the compounds in which the halogen atom is bonded to the sp2-hybridised carbon atom of an aromatic ring.

10.2 Nomenclature

Having learnt the classification of halogenated compounds, let us now learn how these are named. The common names of alkyl halides are derived by naming the alkyl group followed by the halide. Alkyl halides are named as halosubstituted hydrocarbons in the IUPAC system of nomenclature. Haloarenes are the common as well as IUPAC names of aryl halides. For dihalogen derivatives, the prefixes o-, m-, p- are used in common system but in IUPAC system, the numerals 1,2; 1,3 and 1,4 are used.

The dihaloalkanes having the same type of halogen atoms are named as alkylidene or alkylene dihalides. The dihalo-compounds having same type of halogen atoms are further classified as geminal halides (halogen atoms are present on the same carbon atom) and vicinal halides (halogen atoms are present on the adjacent carbon atoms). In common name system, gem-dihalides are named as alkylidene halides and vic-dihalides are named as alkylene dihalides. In IUPAC system, they are named as dihaloalkanes.

Some common examples of halocompounds are mentioned in Table 10.1.

Table 10.1: Common and IUPAC Names of some Halides
Structure Common name IUPAC name
CH3CH2CH(Cl)CH3 sec – Butyl chloride 2 – Chlorobutane
(CH3)3CCH2Br neo-Pentyl bromide 1-Bromo-2,2-dimethylpropane
(CH3)3CBr tert-Butyl bromide 2-Bromo-2-methylpropane
CH2 = CHCl Vinyl chloride Chloroethane
CH2= CHCH2Br Allyl bromide 3-Bromopropane
o-Chlorotoluene 1-Chloro-2-methylbenzene or 2-cholorotoluene
Benzyl chloride Chlorophenylmethane
CH2Cl2 Methylene chloride Dichloromethane
CHCl3 Chloroform Trichloromethane
CHBr3 Bromoform Tribromomethane
CCl4 Carbon tetrachloride Tetrachloromethane
CH3CH2CH2F n-Propyl fluoride 1-Fluoropropane

Example 10.1 Draw the structures of all the eight structural isomers that have the molecular formula C5H11Br. Name each isomer according to IUPAC system and classify them as primary, secondary or tertiary bromide.
Solution
CH3CH2CH2CH2CH2Br       1-Bromopentane (1 °)
CH3CH2CH2CH(Br)CH3      2-Bromopentane(2 °)
CH3CH2CH(Br)CH2CH3      3-Bromopentane (2 °)
(CH3)2CHCH2CH2Br      1-Bromo-3-methylbutane (1 ° )
(CH3)2CHCHBrCH3      2-Bromo-3-methylbutane(2°)
(CH3)2CBrCH2CH3      2-Bromo-2-methylbutane (3°)
CH3CH2CH(CH3)CH2Br      1-Bromo-2-methylbutane(1°)
(CH3)3CCH2Br      1-Bromo-2,2-dimethylpropane (1°)

Example 10.2
Write IUPAC names of the following:

Solution
(i) 4-Bromopent-2-ene
(ii) 3-Bromo-2-methylbut-1-ene
(iii) 4-Bromo-3-methylpent-2-ene
(iv) 1-Bromo-2-methylbut-2-ene
(v) 1-Bromobut-2-ene
(vi) 3-Bromo-2-methylpropene

Intext Question
10.1 Write structures of the following compounds:
(i) 2-Chloro-3-methylpentane
(ii) 1-Chloro-4-ethylcyclohexane
(iii) 4-tert. Butyl-3-iodoheptane
(iv) 1,4-Dibromobut-2-ene
(v) 1-Bromo-4-sec. butyl-2-methylbenzene.

10.3 Nature of C-X Bond

Since halogen atoms are more electronegative than carbon, the carbon- halogen bond of alkyl halide is polarised; the carbon atom bears a partial positive charge whereas the halogen atom bears a partial negative charge.

Since the size of halogen atom increases as we go down the group in the periodic table, fluorine atom is the smallest and iodine atom, the largest. Consequently the carbon-halogen bond length also increases from C—F to C—I. Some typical bond lengths, bond enthalpies and dipole moments are given in Table 10.2.

Table 10.2: Carbon-Halogen (C-X) Bond Lengths, Bond Enthalpies and Dipole Moments
Bond Bond lenth/pm C-X Bond enthalpies/kJmol-1 Dipole moment/Debye
CH3-F 139 452 1.847
CH3-Cl 178 351 1.860
CH3-Br 193 1.830
CH3 -I 214 234 1.639

10.4 Methods of Preparation

10.4.1 From Alcohols

Alkyl halides are best prepared from alcohols, which are easily accessible. The hydroxyl group of an alcohol is replaced by halogen on reaction with concentrated halogen acids, phosphorus halides or thionyl chloride. Thionyl chloride is preferred because the other two products are escapable gases. Hence the reaction gives pure alkyl halides. Phosphorus tribromide and triiodide are usually generated in situ (produced in the reaction mixture) by the reaction of red phosphorus with bromine and iodine respectively. The preparation of alkyl chloride is carried out either by passing dry hydrogen chloride gas through a solution of alcohol or by heating a solution of alcohol in concentrated aqueous acid.

The reactions of primary and secondary alcohols with HX require the presence of a catalyst, ZnCl2. With tertiary alcohols, the reaction is conducted by simply shaking with concentrated HCl at room temperature. Constant boiling with HBr (48%) is used for preparing alkyl bromide. Good yields of R—I may be obtained by heating alcohols with sodium or potassium iodide in 95% phosphoric acid. The order of reactivity of alcohols with a given haloacid is 3°>2°>1°. The above method is not applicable for the preparation of aryl halides because the carbon-oxygen bond in phenols has a partial double bond character and is difficult to break being stronger than a single bond (Unit 11, Class XI).

10.4.2 From Hydrocarbons

(a) By free radical halogenation

Free radical chlorination or bromination of alkanes gives a complex mixture of isomeric mono- and polyhaloalkanes, which is difficult to separate as pure compounds. Consequently, the yield of any one compound is low (Unit 13, Class XI).

Example 10.3
Identify all the possible monochloro structural isomers expected to be formed on free radical monochlorination of (CH3)2CHCH2CH3.
Solution
In the given molecule, there are four different types of hydrogen atoms. Replacement of these hydrogen atoms will give the following
(CH3)2CHCH2CH2Cl       (CH3)2CHCH(Cl)CH3
(CH3)2C(Cl)CH2CH3       CH3CH(CH2Cl)CH2CH3

(b) By electrophilic substitution

Aryl chlorides and bromides can be easily prepared by electrophilic substitution of arenes with chlorine and bromine respectively in the presence of Lewis acid catalysts like iron or iron(III) chloride.

The ortho and para isomers can be easily separated due to large difference in their melting points. Reactions with iodine are reversible in nature and require the presence of an oxidising agent (HNO3, HIO4) to oxidise the HI formed during iodination. Fluoro compounds are not prepared by this method due to high reactivity of fluorine.

(c) Sandmeyer’s reaction

When a primary aromatic amine, dissolved or suspended in cold aqueous mineral acid, is treated with sodium nitrite, a diazonium salt is formed (Unit 13, Class XII). Mixing the solution of freshly prepared diazonium salt with cuprous chloride or cuprous bromide results in the replacement of the diazonium group by –Cl or –Br.

Replacement of the diazonium group by iodine does not require the presence of cuprous halide and is done simply by shaking the diazonium salt with potassium iodide.

(d) From alkenes

(i) Addition of hydrogen halides: An alkene is converted to corresponding alkyl halide by reaction with hydrogen chloride, hydrogen bromide or hydrogen iodide.

Propene yields two products, however only one predominates as per Markovnikov’s rule. (Unit 13, Class XI)
CH3=CH2 + H-I → CH3CH2CH2I + CH3CHICH3
minor              major

(ii) Addition of halogens: In the laboratory, addition of bromine in CCl4 to an alkene resulting in discharge of reddish brown colour of bromine constitutes an important method for the detection of double bond in a molecule. The addition results in the synthesis of vic-dibromides, which are colourless (Unit 13, Class XI).

Example 10.4
Write the products of the following reactions:

Solution

10.4.3 Halogen Exchange

Alkyl iodides are often prepared by the reaction of alkyl chlorides/ bromides with NaI in dry acetone. This reaction is known as Finkelstein reaction.
R-X + NaI → R-I + NaX
X=Cl, Br
NaCl or NaBr thus formed is precipitated in dry acetone. It facilitates the forward reaction according to Le Chatelier’s Principle.
The synthesis of alkyl fluorides is best accomplished by heating an alkyl chloride/bromide in the presence of a metallic fluoride such as AgF, Hg2F2, CoF2 or SbF3. The reaction is termed as Swarts reaction.
H3C-Br +AgF → H3C-F + AgBr

Intext Questions
10.2 Why is sulphuric acid not used during the reaction of alcohols with KI?
10.3 Write structures of different dihalogen derivatives of propane.
10.4 Among the isomeric alkanes of molecular formula C5H12, identify the one that on photochemical chlorination yields
(i) A single monochloride.
(ii) Three isomeric monochlorides.
(iii) Four isomeric monochlorides.
10.5 Draw the structures of major monohalo products in each of the following reactions:

10.5 Physical properties

Alkyl halides are colourless when pure. However, bromides and iodides develop colour when exposed to light. Many volatile halogen compounds have sweet smell.

Melting and boiling points

Methyl chloride, methyl bromide, ethyl chloride and some chlorofluoromethanes are gases at room temperature. Higher members are liquids or solids. As we have already learnt, molecules of organic halogen compounds are generally polar. Due to greater polarity as well as higher molecular mass as compared to the parent hydrocarbon, the intermolecular forces of attraction (dipole-dipole and van der Waals) are stronger in the halogen derivatives. That is why the boiling points of chlorides, bromides and iodides are considerably higher than those of the hydrocarbons of comparable molecular mass.
The attractions get stronger as the molecules get bigger in size and have more electrons. The pattern of variation of boiling points of different halides is depicted in Fig. 10.1. For the same alkyl group, the boiling points of alkyl halides decrease in the order: RI> RBr> RCl> RF. This is because with the increase in size and mass of halogen atom, the magnitude of van der Waal forces increases.

The boiling points of isomeric haloalkanes decrease with increase in branching (Unit 12, Class XI). For example, 2-bromo-2-methylpropane has the lowest boiling point among the three isomers.

Boiling points of isomeric dihalobenzenes are very nearly the same. However, the para-isomers are high melting as compared to their ortho- and meta-isomers. It is due to symmetry of para-isomers that fits in crystal lattice better as compared to ortho- and meta-isomers.

Density

Bromo, iodo and polychloro derivatives of hydrocarbons are heavier than water. The density increases with increase in number of carbon atoms, halogen atoms and atomic mass of the halogen atoms (Table 10.3).

Table 10.3: Density of Some Haloalkanes
Compound Density(g/ml) Compound Density (g/mL)
n-C3H7Cl 0.89 CH2Cl2 1.336
n-C3H7Br 1.335 CHCl3 1.489
C3H7I 1.747 CCl4 1.595
CH3 -I 214 234 1.639

Solubility

The haloalkanes are only very slightly soluble in water. In order for a haloalkane to dissolve in water, energy is required to overcome the attractions between the haloalkane molecules and break the hydrogen bonds between water molecules. Less energy is released when new attractions are set up between the haloalkane and the water molecules as these are not as strong as the original hydrogen bonds in water. As a result, the solubility of haloalkanes in water is low. However, haloalkanes tend to dissolve in organic solvents because the new intermolecular attractions between haloalkanes and solvent molecules have much the same strength as the ones being broken in the separate haloalkane and solvent molecules.

Intext Question
10.6 Arrange each set of compounds in order of increasing boiling points.
(i) Bromomethane, Bromoform, Chloromethane, Dibromomethane.
(ii) 1-Chloropropane, Isopropyl chloride, 1-Chlorobutane.

10.6 Chemical Reactions

10.6.1 Reactions of Haloalkanes

The reactions of haloalkanes may be divided into the following categories:
(i) Nucleophilic substitution
(ii) Elimination reactions
(iii) Reaction with metals.

(i) Nucleophilic substitution reactions
In this type of reaction, a nucleophile reacts with haloalkane (the substrate) having a partial positive charge on the carbon atom bonded to halogen. A substitution reaction takes place and halogen atom, called leaving group departs as halide ion. Since the substitution reaction is initiated by a nucleophile, it is called nucleophilic substitution reaction.

It is one of the most useful classes of organic reactions of alkyl halides in which halogen is bonded to sp3 hybridised carbon. The products formed by the reaction of haloalkanes with some common nucleophiles are given in Table 10.4.

Table 10.4: Nucleophilic Substitution of Alkyl Halides (R–X)R-X+Nu-→R-Nu+X-
Reagent Nucleophile(Nu-) Substitution product R-Nu Class of main product
NaOH(KOH) HO- ROH Alcohol
H2O H2O ROH Alcohol
NaOR’ R’O- ROR’ Ether
NaI I- R-I Alkyl iodide
NH3 NH3 RNH2 Primary amine
R’NH2 R’NH2 R’NHR2 Sec. amine
R’R”NH2 R’R”NH2 RNR’R”2 Tert. amine
KCN RCN Nitrile (cyanide)
AgCN RNC (isosynanide) Isonitrile
KNO2 O=N-O R-O-N=O (isosynanide) Alkyl nitrite
AgNO2 R-NO2 Nitroalkane
R’COOAg R’COO- R’COOR Ester
LiAlH4 H RH (isosynanide) Hydrocarbon
R’-M+ R’- RR- Alkane

Groups like cyanides and nitrites possess two nucleophilic centres and are called ambident nucleophiles. Actually cyanide group is a hybrid of two contributing structures and therefore can act as a nucleophile in two different ways [ΘC≡N ↔ :C=NΘ], i.e., linking through carbon atom resulting in alkyl cyanides and through nitrogen atom leading to isocyanides. Similarly nitrite ion also represents an ambident nucleophile with two different points of linkage . The linkage through oxygen results in alkyl nitrites while through nitrogen atom, it leads to nitroalkanes.

Example 10.5
Haloalkanes react with KCN to form alkyl cyanides as main product while AgCN forms isocyanides as the chief product. Explain.
Solution
KCN is predominantly ionic and provides cyanide ions in solution. Although both carbon and nitrogen atoms are in a position to donate electron pairs, the attack takes place mainly through carbon atom and not through nitrogen atom since C—C bond is more stable than C—N bond. However, AgCN is mainly covalent in nature and nitrogen is free to donate electron pair forming isocyanide as the main product.

Mechanism: This reaction has been found to proceed by two different mechanims which are described below:
(a) Substitution nucleophilic bimolecular (SN2)

The reaction between CH3Cl and hydroxide ion to yield methanol and chloride ion follows a second order kinetics, i.e., the rate depends upon the concentration of both the reactants.

As you have already learnt in Section 12.3.2 of Class XI, the solid wedge represents the bond coming out of the paper, dashed line going down the paper and a straight line representing bond in the plane of the paper.

This can be represented diagrammatically as shown in Fig. 10.2.

It depicts a bimolecular nucleophilic displacement (SN2) reaction; the incoming nucleophile interacts with alkyl halide causing the carbon- halide bond to break while forming a new carbon-OH bond. These two processes take place simultaneously in a single step and no intermediate is formed. As the reaction progresses and the bond between the nucleophile and the carbon atom starts forming, the bond between carbon atom and leaving group weakens. As this happens, the configuration of carbon atom under attack inverts in much the same way as an umbrella is turned inside out when caught in a strong wind, while the leaving group is pushed away. This process is called as inversion of configuration. In the transition state, the carbon atom is simultaneously bonded to incoming nucleophile and the outgoing leaving group and such structures are unstable and cannot be isolated. This is because the carbon atom in the transition state is simultaneously bonded to five atoms and therefore is unstable.

Since this reaction requires the approach of the nucleophile to the carbon bearing the leaving group, the presence of bulky substituents on or near the carbon atom have a dramatic inhibiting effect. Of the simple alkyl halides, methyl halides react most rapidly in SN2 reactions because there are only three small hydrogen atoms. Tertiary halides are the least reactive because bulky groups hinder the approaching nucleophiles. Thus the order of reactivity followed is:
Primary halide > Secondary halide > Tertiary halide.

(b) Substitution nucleophilic unimolecular (SN1)

SN1 reactions are generally carried out in polar protic solvents (like water, alcohol, acetic acid, etc.). The reaction between tert-butyl bromide and hydroxide ion yields tert-butyl alcohol and follows the first order kinetics, i.e., the rate of reaction depends upon the concentration of only one reactant, which is tert- butyl bromide.

It occurs in two steps. In step I, the polarised C—Br bond undergoes slow cleavage to produce a carbocation and a bromide ion. The carbocation thus formed is then attacked by nucleophile in step II to complete the substitution reaction.

Step I is the slowest and reversible. It involves the C–Br bond breaking for which the energy is obtained through solvation of halide ion with the proton of protic solvent. Since the rate of reaction depends upon the slowest step, the rate of reaction depends only on the concentration of alkyl halide and not on the concentration of hydroxide ion. Further, greater the stability of carbocation, greater will be its ease of formation from alkyl halide and faster will be the rate of reaction. In case of alkyl halides, 3° alkyl halides undergo SN1 reaction very fast because of the high stability of 3° carbocations. We can sum up the order of reactivity of alkyl halides towards SN1 and SN2 reactions as follows:

For the same reasons, allylic and benzylic halides show high reactivity towards the SN1 reaction. The carbocation thus formed gets stabilised through resonance (Unit 12, Class XI) as shown below:

For a given alkyl group, the reactivity of the halide, R-X, follows the same order in both the mechanisms R–I> R–Br>R–Cl>>R–F.

Example 10.6
In the following pairs of halogen compounds, which would undergo SN2 reaction faster?

Solution

Example 10.7
Predict the order of reactivity of the following compounds in SN1 and SN2 reactions:
(i) The four isomeric bromobutanes
(ii) C6H5CH2Br, C6H5CH(C6H5)Br, C6H5CH(CH3)Br, C6H5C(CH3)(C6H5)Br
Solution
(i) CH3CH2CH2CH2Br < (CH3)2CHCH2Br < CH3CH2CH(Br)CH3 < (CH3)3CBr (SN1)
CH3CH2CH2CH2Br > (CH3)2CHCH2Br > CH3CH2CH(Br)CH3 > (CH3)3CBr (SN2)
Of the two primary bromides, the carbocation intermediate derived from (CH3)2CHCH2Br is more stable than derived from CH3CH2CH2CH2Br because of greater electron donating inductive effect of (CH3)2CH- group. Therefore, (CH3)2CHCH2Br is more reactive than CH3CH2CH2CH2Br in SN1 reactions. CH3CH2CH(Br)CH3 is a secondary bromide and (CH3)3CBr is a tertiary bromide. Hence the above order is followed in SN1. The reactivity in SN2 reactions follows the reverse order as the steric hinderance around the electrophilic carbon increases in that order.
ii) C6H5C(CH3)(C6H5)Br > C6H5CH(C6H5)Br > C6H5CH(CH3)Br > C6H5CH2Br (SN1)
C6H5C(CH3)(C6H5)Br < C6H5CH(C6H5)Br < C6H5CH(CH3)Br < C6H5CH2Br (SN2)
Of the two secondary bromides, the carbocation intermediate obtained from C6H5CH(C6H5)Br is more stable than obtained from C6H5CH(CH3)Br because it is stabilised by two phenyl groups due to resonance. Therefore, the former bromide is more reactive than the latter in SN1 reactions. A phenyl group is bulkier than a methyl group. Therefore, C6H5CH(C6H5)Br is less reactive than C6H5CH(CH3)Br in SN2 reactions.

(c) Stereochemical aspects of nucleophilic substitution reactions A SN2 reaction proceeds with complete stereochemical inversion while a SN1 reaction proceeds with racemisation.
In order to understand this concept, we need to learn some basic stereochemical principles and notations (optical activity, chirality, retention, inversion, racemisation, etc.).

(i) Plane polarised light and optical activity: Certain compounds rotate the plane polarised light (produced by passing ordinary light through Nicol prism) when it is passed through their solutions. Such compounds are called optically active compounds. The angle by which the plane polarised light is rotated is measured by an instrument called polarimeter. If the compound rotates the plane polarised light to the right, i.e., clockwise direction, it is called dextrorotatory (Greek for right rotating) or the d-form and is indicated by placing a positive (+)sign before the degree of rotation. If the light is rotated towards left (anticlockwise direction), the compound is said to be laevo- rotatory or the l-form and a negative (–) sign is placed before the degree of rotation. Such (+) and (–) isomers of a compound are called optical isomers and the phenomenon is termed as optical isomerism.

(ii) Molecular asymmetry, chirality and enantiomers: The observation of Louis Pasteur (1848) that crystals of certain compounds exist in the form of mirror images laid the foundation of modern stereochemistry. He demonstrated that aqueous solutions of both types of crystals showed optical rotation, equal in magnitude (for solution of equal concentration) but opposite in direction. He believed that this difference in optical activity was associated with the three dimensional arrangements of atoms (configurations) in two types of crystals. Dutch scientist, J. Van’t Hoff and French scientist, C. Le Bel in the same year (1874), independently argued that the spatial arrangement of four groups (valencies) around a central carbon is tetrahedral and if all the substituents attached to that carbon are different, such a carbon is called asymmetric carbon or stereocentre. The resulting molecule would lack symmetry and is referred to as asymmetric molecule. The asymmetry of the molecule is responsible for the optical activity in such organic compounds.

The symmetry and asymmetry are also observed in many day to day objects: a sphere, a cube, a cone, are all identical to their mirror images and can be superimposed. However, many objects are non superimposable on their mirror images. For example, your left and right hand look similar but if you put your left hand on your right hand, they do not coincide. The objects which are non- superimposable on their mirror image (like a pair of hands) are said to be chiral and this property is known as chirality. While the objects, which are, superimposable on their mirror images are called achiral.

The above test of molecular chirality can be applied to organic molecules by constructing models and its mirror images or by drawing three dimensional structures and attempting to superimpose them in our minds. There are other aids, however, that can assist us in recognising chiral molecules. One such aid is the presence of a single asymmetric carbon atom. Let us consider two simple molecules propan-2-ol and butan-2-ol and their mirror images.

As you can see very clearly, propan-2-ol does not contain an asymmetric carbon, as all the four groups attached to the tetrahedral carbon are not different. Thus it is an achiral molecule.

Butan-2-ol has four different groups attached to the tetrahedral carbon and as expected is chiral. Some common examples of chiral molecules such as 2-chlorobutane, 2, 3-dihyroxypropanal, (OHC–CHOH–CH2OH), bromochloro-iodomethane (BrClCHI), 2-bromopropanoic acid (H3C–CHBr–COOH), etc. The stereoisomers related to each other as non- superimposable mirror images are called enantiomers (Fig. 10.5).

Enantiomers possess identical physical properties namely, melting point, boiling point, solubility, refractive index, etc. They only differ with respect to the rotation of plane polarised light. If one of the enantiomer is dextro rotatory, the other will be laevo rotatory.

However, the sign of optical rotation is not necessarily related to the absolute configuration of the molecule.

A mixture containing two enantiomers in equal proportions will have zero optical rotation, as the rotation due to one isomer will be cancelled by the rotation due to the other isomer. Such a mixture is known as racemic mixture or racemic modification. A racemic mixture is represented by prefixing dl or (±) before the name, for example (±) butan-2-ol. The process of conversion of enantiomer into a racemic mixture is known as racemisation.

Example 10.8
Identify chiral and achiral molecules in each of the following pair of compounds. (Wedge and Dash representations according to Class XI, Fig 12.1).

Solution

(iii) Retention: Retention of configuration is the preservation of integrity of the spatial arrangement of bonds to an asymmetric centre during a chemical reaction or transformation. It is also the configurational correlation when a chemical species XCabc is converted into the chemical species YCabc having the same relative configuration.

In general, if during a reaction, no bond to the stereocentre is broken, the product will have the same general configuration of groups around the stereocentre as that of reactant. Such a reaction is said to proceed with retention of the configuration. Consider as an example, the reaction that takes place when (–)-2-methylbutan-1-ol is heated with concentrated hydrochloric acid.

(iv) Inversion, retention and racemisation: There are three outcomes for a reaction at an asymmetric carbon atom. Consider the replacement of a group X by Y in the following reaction;

If (A) is the only compound obtained, the process is called retention of configuration.

If (B) is the only compound obtained, the process is called inversion of configuration.

If a 50:50 mixture of the above two is obtained then the process is called racemisation and the product is optically inactive, as one isomer will rotate light in the direction opposite to another.

Now let us have a fresh look at SN1 and SN2 mechanisms by taking examples of optically active alkyl halides.
In case of optically active alkyl halides, the product formed as a result of SN2 mechanism has the inverted configuration as compared to the reactant. This is because the nucleophile attaches itself on the side opposite to the one where the halogen atom is present. When (–)-2-bromooctane is allowed to react with sodium hydroxide, (+)-octan-2-ol is formed with the –OH group occupying the position opposite to what bromide had occupied.

Thus, SN2 reactions of optically active halides are accompanied by inversion of configuration.

In case of optically active alkyl halides, SN1 reactions are accompanied by racemisation. Can you think of the reason why it happens? Actually the carbocation formed in the slow step being sp2 hybridised is planar (achiral). The attack of the nucleophile may be accomplished from either side resulting in a mixture of products, one having the same configuration (the –OH attaching on the same position as halide ion) and the other having opposite configuration (the –OH attaching on the side opposite to halide ion). This may be illustrated by hydrolysis of optically active 2-bromobutane, which results in the formation of (±)-butan-2-ol.

2. Elimination reactions

When a haloalkane with β-hydrogen atom is heated with alcoholic solution of potassium hydroxide, there is elimination of hydrogen atom from β-carbon and a halogen atom from the α-carbon atom. As a result, an alkene is formed as a product. Since β-hydrogen atom is involved in elimination, it is often called β-elimination.

If there is possibility of formation of more than one alkene due to the availability of more than one β-hydrogen atoms, usually one alkene is formed as the major product. These form part of a pattern first observed by Russian chemist, Alexander Zaitsev (also pronounced as Saytzeff) who in 1875 formulated a rule which can be summarised as “in dehydrohalogenation reactions, the preferred product is that alkene which has the greater number of alkyl groups attached to the doubly bonded carbon atoms.” Thus, 2-bromopentane gives pent-2-ene as the major product.

Ellimination versus substitution

A chemical reaction is the result of competition; it is a race that is won by the fastest runner. A collection of molecules tend to do, by and large, what is easiest for them. An alkyl halide with α-hydrogen atoms when reacted with a base or a nucleophile has two competing routes: substitution (SN1 and SN2) and elimination. Which route will be taken up depends upon the nature of alkyl halide, strength and size of base/nucleophile and reaction conditions. Thus, a bulkier nucleophile will prefer to act as a base and abstracts a proton rather than approach a tetravalent carbon atom (steric reasons) and vice versa. Similarly, a primary alkyl halide will prefer a SN2 reaction, a secondary halide- SN2 or elimination depending upon the strength of base/nucleophile and a tertiary halide- SN1 or elimination depending upon the stability of carbocation or the more substituted alkene.

3. Reaction with metals

Most organic chlorides, bromides and iodides react with certain metals to give compounds containing carbon-metal bonds. Such compounds are known as organo-metallic compounds. An important class of organo-metallic compounds discovered by Victor Grignard in 1900 is alkyl magnesium halide, RMgX, referred as Grignard Reagents. These reagents are obtained by the reaction of haloalkanes with magnesium metal in dry ether.

Victor Grignard had a strange start in academic life for a chemist – he took a maths degree. When he eventually switched to chemistry, it was not to the mathematical province of physical chemistry but to organic chemistry. While attempting to find an efficient catalyst for the process of methylation, he noted that Zn in diethyl ether had been used for this purpose and wondered whether the Mg/ether combination might be successful. Grignard reagents were first reported in 1900 and Grignard used this work for his doctoral thesis in 1901. In 1910, Grignard obtained a professorship at the University of Nancy and in 1912, he was awarded the Nobel prize for Chemistry which he shared with Paul Sabatier who had made advances in nickel catalysed hydrogenation.

In the Grignard reagent, the carbon-magnesium bond is covalent but highly polar, with carbon pulling electrons from electropositive magnesium; the magnesium halogen bond is essentially ionic.

Grignard reagents are highly reactive and react with any source of proton to give hydrocarbons. Even water, alcohols, amines are sufficiently acidic to convert them to corresponding hydrocarbons.
RMgX + H2O &RARR; RH + Mg(OH)X
It is therefore necessary to avoid even traces of moisture from a Grignard reagent. On the other hand, this could be considered as one of the methods for converting halides to hydrocarbons.

Wurtz reaction

Alkyl halides react with sodium in dry ether to give hydrocarbons containing double the number of carbon atoms present in the halide. This reaction is known as Wurtz reaction. (Unit 13, Class XI).
2RX + 2Na &RARR; RR-2NaX

10.6.2 Reactions of Haloarenes

1. Nucleophilic substitution
Aryl halides are extremely less reactive towards nucleophilic substitution reactions due to the following reasons:
(i) Resonance effect : In haloarenes, the electron pairs on halogen atom are in conjugation with π-electrons of the ring and the following resonating structures are possible.

C—Cl bond acquires a partial double bond character due to resonance. As a result, the bond cleavage in haloarene is difficult than haloalkane and therefore, they are less reactive towards nucleophilic substitution reaction.

(ii) Difference in hybridisation of carbon atom in C—X bond: In haloalkane, the carbon atom attached to halogen is sp3 hybridised while in case of haloarene, the carbon atom attached to halogen is sp2-hybridised.

The sp2 hybridised carbon with a greater s-character is more electronegative and can hold the electron pair of C—X bond more tightly than sp3-hybridised carbon in haloalkane with less s-chararcter. Thus, C—Cl bond length in haloalkane is 177pm while in haloarene is 169 pm. Since it is difficult to break a shorter bond than a longer bond, therefore, haloarenes are less reactive than haloalkanes towards nucleophilic substitution reaction.
(iii) Instability of phenyl cation: In case of haloarenes, the phenyl cation formed as a result of self-ionisation will not be stabilised by resonance and therefore, SN1 mechanism is ruled out.
(iv) Because of the possible repulsion, it is less likely for the electron rich nucleophile to approach electron rich arenes.

Replacement by hydroxyl group

Chlorobenzene can be converted into phenol by heating in aqueous sodium hydroxide solution at a temperature of 623K and a pressure of 300 atmospheres.

The presence of an electron withdrawing group (-NO2) at ortho- and para-positions increases the reactivity of haloarenes.


The effect is pronounced when (-NO2) group is introduced at ortho- and para- positions. However, no effect on reactivity of haloarenes is observed by the presence of electron withdrawing group at meta-position. Mechanism of the reaction is as depicted:

Can you think why does NO2 group show its effect only at ortho- and para- positions and not at meta- position?
As shown, the presence of nitro group at ortho- and para-positions withdraws the electron density from the benzene ring and thus facilitates the attack of the nucleophile on haloarene. The carbanion thus formed is stabilised through resonance. The negative charge appeared at ortho- and para- positions with respect to the halogen substituent is stabilised by –NO2 group while in case of meta-nitrobenzene, none of the resonating structures bear the negative charge on carbon atom bearing the –NO2 group. Therefore, the presence of nitro group at meta- position does not stabilise the negative charge and no effect on reactivity is observed by the presence of –NO2 group at meta-position.

2. Electrophilic substitution reactions

Haloarenes undergo the usual electrophilic reactions of the benzene ring such as halogenation, nitration, sulphonation and Friedel-Crafts reactions. Halogen atom besides being slightly deactivating is o, p- directing; therefore, further substitution occurs at ortho- and para- positions with respect to the halogen atom. The o, p-directing influence of halogen atom can be easily understood if we consider the resonating structures of halobenzene as shown:

Due to resonance, the electron density increases more at ortho- and para-positions than at meta-positions. Further, the halogen atom because of its –I effect has some tendency to withdraw electrons from the benzene ring. As a result, the ring gets somewhat deactivated as compared to benzene and hence the electrophilic substitution reactions in haloarenes occur slowly and require more drastic conditions as compared to those in benzene.
(i) Halogenation

(iv) Friedel-Crafts reaction

Example 10.9 Although chlorine is an electron withdrawing group, yet it is ortho-, para- directing in electrophilic aromatic substitution reactions. Why?
Solution
Chlorine withdraws electrons through inductive effect and releases electrons through resonance. Through inductive effect, chlorine destabilises the intermediate carbocation formed during the electrophilic substitution.

Through resonance, halogen tends to stabilise the carbocation and the effect is more pronounced at ortho- and para- positions. The inductive effect is stronger than resonance and causes net electron withdrawal and thus causes net deactivation. The resonance effect tends to oppose the inductive effect for the attack at ortho- and para- positions and hence makes the deactivation less for ortho- and para- attack. Reactivity is thus controlled by the stronger inductive effect and orientation is controlled by resonance effect.

3. Reaction with metals

Wurtz-Fittig reaction
A mixture of an alkyl halide and aryl halide gives an alkylarene when treated with sodium in dry ether and is called Wurtz-Fittig reaction.

Fittig reaction
Aryl halides also give analogous compounds when treated with sodium in dry ether, in which two aryl groups are joined together. It is called Fittig reaction.

Intext Questions
10.7 Which alkyl halide from the following pairs would you expect to react more rapidly by an SN2 mechanism? Explain your answer.

10.8 In the following pairs of halogen compounds, which compound undergoes faster SN1 reaction?

10.9 Identify A, B, C, D, E, R and R1 in the following:

10.7 Polyhalogen Compounds

Carbon compounds containing more than one halogen atom are usually referred to as polyhalogen compounds. Many of these compounds are useful in industry and agriculture. Some polyhalogen compounds are described in this section.

10.7.1 Dichloro- methane (Methylene chloride)

Dichloromethane is widely used as a solvent as a paint remover, as a propellant in aerosols, and as a process solvent in the manufacture of drugs. It is also used as a metal cleaning and finishing solvent. Methylene chloride harms the human central nervous system. Exposure to lower levels of methylene chloride in air can lead to slightly impaired hearing and vision. Higher levels of methylene chloride in air cause dizziness, nausea, tingling and numbness in the fingers and toes. In humans, direct skin contact with methylene chloride causes intense burning and mild redness of the skin. Direct contact with the eyes can burn the cornea.

10.7.2 Trichloro-methane (Chloroform)

Iodine and other substances. The major use of chloroform today is in Chemically, chloroform is employed as a solvent for fats, alkaloids, (Chloroform) the production of the freon refrigerant R-22. It was once used as a general anaesthetic in surgery but has been replaced by less toxic, safer anaesthetics, such as ether. As might be expected from its use as an anaesthetic, inhaling chloroform vapours depresses the central nervous system. Breathing about 900 parts of chloroform per million parts of air (900 parts per million) for a short time can cause dizziness, fatigue, and headache. Chronic chloroform exposure may cause damage to the liver (where chloroform is metabolised to phosgene) and to the kidneys, and some people develop sores when the skin is immersed in chloroform. Chloroform is slowly oxidised by air in the presence of light to an extremely poisonous gas, carbonyl chloride, also known as phosgene. It is therefore stored in closed dark coloured bottles completely filled so that air is kept out.

10.7.3 Triiodo-methane (Iodoform)

It was used earlier as an antiseptic but the antiseptic properties are due to the liberation of free iodine and not due to iodoform itself. Due to its objectionable smell, it has been replaced by other formulations containing iodine.

10.7.4 Tetrachlo- romethane (Carbon tetrachloride)

It is produced in large quantities for use in the manufacture of refrigerants and propellants for aerosol cans. It is also used as feedstock in the synthesis of chlorofluorocarbons and other chemicals, pharmaceutical manufacturing, and general solvent use. Until the mid 1960s, it was also widely used as a cleaning fluid, both in industry, as a degreasing agent, and in the home, as a spot remover and as fire extinguisher. There is some evidence that exposure to carbon tetrachloride causes liver cancer in humans. The most common effects are dizziness, light headedness, nausea and vomiting, which can cause permanent damage to nerve cells. In severe cases, these effects can lead rapidly to stupor, coma, unconsciousness or death. Exposure to CCl4 can make the heart beat irregularly or stop. The chemical may irritate the eyes on contact. When carbon tetrachloride is released into the air, it rises to the atmosphere and depletes the ozone layer. Depletion of the ozone layer is believed to increase human exposure to ultraviolet rays, leading to increased skin cancer, eye diseases and disorders, and possible disruption of the immune system.

10.7.5 Freons

The chlorofluorocarbon compounds of methane and ethane are collectively known as freons. They are extremely stable, unreactive, non-toxic, on-corrosive and easily liquefiable gases. Freon 12 (CCl2F2) is one of the most common freons in industrial use. It is manufactured from tetrachloromethane by Swarts reaction. These are usually produced for aerosol propellants, refrigeration and air conditioning purposes. By 1974, total freon production in the world was about 2 billion pounds annually. Most freon, even that used in refrigeration, eventually makes its way into the atmosphere where it diffuses unchanged into the stratosphere. In stratosphere, freon is able to initiate radical chain reactions that can upset the natural ozone balance (Unit 14, Class XI).

10.7.6 p,p-Dichlorodiphenyl trichloro ethane(DDT)

DDT, the first chlorinated organic insecticides, was originally prepared in 1873, but it was not until 1939 that Paul Muller of Geigy Pharmaceuticals in Switzerland discovered the effectiveness of DDT as an insecticide. Paul Muller was awarded the Nobel Prize in Medicine and Physiology in 1948 for this discovery. The use of DDT increased enormously on a worldwide basis after World War II, primarily because of its effectiveness against the mosquito that spreads malaria and lice that carry typhus. However, problems related to extensive use of DDT began to appear in the late 1940s. Many species of insects developed resistance to DDT, and it was also discovered to have a high toxicity towards fish. The chemical stability of DDT and its fat solubility compounded the problem. DDT is not metabolised very rapidly by animals; instead, it is deposited and stored in the fatty tissues. If ingestion ontinues at a steady rate, DDT builds up within the animal over time. The use of DDT was banned in the United States in 1973, although it is still in use in some other parts of the world.

Summary
Alkyl/ Aryl halides may be classified as mono, di, or polyhalogen (tri-, tetra-, etc.) compounds depending on whether they contain one, two or more halogen atoms in their structures. Since halogen atoms are more electronegative than carbon, the carbon- halogen bond of alkyl halide is polarised; the carbon atom bears a partial positive charge, and the halogen atom bears a partial negative charge. Alkyl halides are prepared by the free radical halogenation of alkanes, addition of halogen acids to alkenes, replacement of –OH group of alcohols with halogens using phosphorus halides, thionyl chloride or halogen acids. Aryl halides are prepared by electrophilic substitution to arenes. Fluorides and iodides are best prepared by halogen exchange method.
The boiling points of organohalogen compounds are comparatively higher than the corresponding hydrocarbons because of strong dipole-dipole and van der Waals forces of attraction. These are slightly soluble in water but completely soluble in organic solvents.
The polarity of carbon-halogen bond of alkyl halides is responsible for their nucleophilic substitution, elimination and their reaction with metal atoms to form organometallic compounds. Nucleophilic substitution reactions are categorised into SN1 and SN2 on the basis of their kinetic properties. Chirality has a profound role in understanding the reaction mechanisms of SN1 and SN2 reactions. SN2 reactions of chiral alkyl halides are characterised by the inversion of configuration while SN1 reactions are characterised by racemisation.
A number of polyhalogen compounds e.g., dichloromethane, chloroform, iodoform, carbon tetrachloride, freon and DDT have many industrial applications. However, some of these compounds cannot be easily decomposed and even cause depletion of ozone layer and are proving environmental hazards.

Exercise

10.1 Name the following halides according to IUPAC system and classify them as alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
(i) (CH3)2CHCH(Cl)CH3
(ii) CH3CH2CH(CH3)CH(C2H5)Cl
(iii) CH3CH2C(CH3)2CH2I
(iv) (CH3)3CCH2CH(Br)C6H5
(v) CH3CH(CH3)CH(Br)CH3
(vi) CH3C(C2H5)2CH2Br
(vii) CH3C(Cl)(C2H5)CH2CH3
(viii) CH3CH=C(Cl)CH2CH(CH3)2
(ix) CH3CH=CHC(Br)(CH3)2
(x) p-ClC6H4CH2CH(CH3)2
(xi) m-ClCH2C6H4CH2C(CH3)3
(xii) o-Br-C6H4CH(CH3)CH2CH3

10.2 Give the IUPAC names of the following compounds:
(i) CH3CH(Cl)CH(Br)CH3
(ii) CHF2CBrClF
(iii) ClCH2C≡CCH2Br
(iv) (CCl3)3CCl
(v) CH3C(p-ClC6H4)2CH(Br)CH3
(vi) (CH3)3CCH=ClC6H4I-p

10.3 Write the structures of the following organic halogen compounds.
(i) 2-Chloro-3-methylpentane
(ii) p-Bromochlorobenzene
(iii) 1-Chloro-4-ethylcyclohexane
(iv) 2-(2-Chlorophenyl)-1-iodooctane
(v) 2-Bromobutane
(vi) 4-tert-Butyl-3-iodoheptane
(vii) 1-Bromo-4-sec-butyl-2-methylbenzene
(viii) 1,4-Dibromobut-2-ene

10.4 Which one of the following has the highest dipole moment?
(i) CH2Cl2 (ii) CHCl3 (iii) CCl4

10.5 A hydrocarbon C5H10 does not react with chlorine in dark but gives a single monochloro compound C5H9Cl in bright sunlight. Identify the hydrocarbon.

10.6 Write the isomers of the compound having formula C4H9Br.

10.7 Write the equations for the preparation of 1-iodobutane from
(i) 1-butanol
(ii) 1-chlorobutane
(iii) but-1-ene.

10.8 What are ambident nucleophiles? Explain with an example.

10.9 Which compound in each of the following pairs will react faster in SN2 reaction with –OH?
(i) CH3Br or CH3I (ii) (CH3)3CCl or CH3Cl

10.10 Predict all the alkenes that would be formed by dehydrohalogenation of the following halides with sodium ethoxide in ethanol and identify the major alkene:
(i) 1-Bromo-1-methylcyclohexane
(ii) 2-Chloro-2-methylbutane
(iii) 2,2,3-Trimethyl-3-bromopentane.

10.11 How will you bring about the following conversions?
(i) Ethanol to but-1-yne
(ii) Ethane to bromoethene
(iii) Propene to1-nitropropane
(iv) Toluene to benzyl alcohol
(v) Propene to propyne
(vi) Ethanol to ethyl fluoride
(vii) Bromomethane to propanone
(viii) But-1-ene to but-2-ene
(ix) 1-Chlorobutane to n-octane
(x) Benzene to biphenyl.

10.12 Explain why
(i) the dipole moment of chlorobenzene is lower than that of cyclohexyl chloride?
(ii) alkyl halides, though polar, are immiscible with water?
(iii) Grignard reagents should be prepared under anhydrous conditions?

10.13 Give the uses of freon 12, DDT, carbon tetrachloride and iodoform.

10.14 Write the structure of the major organic product in each of the following reactions:

10.15 Write the mechanism of the following reaction:

10.16 Arrange the compounds of each set in order of reactivity towards SN2 displacement:
(i) 2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane
(ii) 1-Bromo-3-methylbutane, 2-Bromo-2-methylbutane, 3-Bromo-2-methylbutane
(iii) 1-Bromobutane, 1-Bromo-2,2-dimethylpropane, 1-Bromo-2-methylbutane, 1-Bromo-3-methylbutane.

10.17 Out of C6H5CH2Cl and C6H5CHClC6H5, which is more easily hydrolysed by aqueous KOH.

10.18 p-Dichlorobenzene has higher m.p. and solubility than those of o- and m-isomers. Discuss.

10.19 How the following conversions can be carried out?
(i) Propene to propan-1-ol
(ii) Ethanol to but-1-yne
(iii) 1-Bromopropane to 2-bromopropane
(iv) Toluene to benzyl alcohol
(v) Benzene to 4-bromonitrobenzene
(vi) Benzyl alcohol to 2-phenylethanoic acid
(vii) Ethanol to propanenitrile
(viii) Aniline to chlorobenzene
(ix) 2-Chlorobutane to 3, 4-dimethylhexane
(x) 2-Methyl-1-propene to 2-chloro-2-methylpropane
(xi) Ethyl chloride to propanoic acid
(xii) But-1-ene to n-butyliodide
(xiii) 2-Chloropropane to 1-propanol
(xiv) Isopropyl alcohol to iodoform
(xv) Chlorobenzene to p-nitrophenol
(xvi) 2-Bromopropane to 1-bromopropane
(xvii) Chloroethane to butane
(xviii) Benzene to diphenyl
(xix) tert-Butyl bromide to isobutyl bromide
(xx) Aniline to phenylisocyanide

10.20 The treatment of alkyl chlorides with aqueous KOH leads to the formation of alcohols but in the presence of alcoholic KOH, alkenes are major products. Explain.

10.21 Primary alkyl halide C4H9Br (a) reacted with alcoholic KOH to give compound (b). Compound (b) is reacted with HBr to give (c) which is an isomer of (a). When (a) is reacted with sodium metal it gives compound (d), C8H18 which is different
from the compound formed when n-butyl bromide is reacted with sodium. Give the structural formula of (a) and write the equations for all the reactions.

10.22 What happens when
(i) n-butyl chloride is treated with alcoholic KOH,
(ii) bromobenzene is treated with Mg in the presence of dry ether,
(iii) chlorobenzene is subjected to hydrolysis,
(iv) ethyl chloride is treated with aqueous KOH,
(v) methyl bromide is treated with sodium in the presence of dry ether,
(vi) methyl chloride is treated with KCN?

Answers to Some Intext Questions

10.1

10.2 (i) H2SO4 cannot be used along with KI in the conversion of an alcohol to an alkyl iodide as it converts KI to corresponding HI and then oxidises it to I2.

10.3 (i) ClCH2CH2CH2Cl (ii) ClCH2CHClCH3 (iii) Cl2CH2CH2CH3 (iv) CH3CCl2CH3

10.4

10.5

10.6 (i) Chloromethane, Bromomethane, Dibromomethane, Bromoform. Boiling point increases with increase in molecular mass.
(ii) Isopropylchloride, 1-Chloropropane, 1-Chlorobutane. Isopropylchloride being branched has lower b.p. than 1-Chloropropane.

10.7

10.8

10.9

Some Useful Links

http://www.freelance-teacher.com/videos.htm

I. Multiple Choice Questions (Type-I)

1. The order of reactivity of following alcohols with halogen acids is ___________.

(A) CH3CH2 —CH2—OH

(i) (A) > (B) > (C)
(ii) (C) > (B) > (A)
(iii) (B) > (A) > (C)
(iv) (A) > (C) > (B)

2. Which of the following alcohols will yield the corresponding alkyl chloride on reaction with concentrated HCl at room temperature?

(i) CH3CH2—CH2—OH

3. Identify the compound Y in the following reaction.

4. Toluene reacts with a halogen in the presence of iron (III) chloride giving ortho and para halo compounds. The reaction is

(i) Electrophilic elimination reaction
(ii) Electrophilic substitution reaction
(iii) Free radical addition reaction
(iv) Nucleophilic substitution reaction

5. Which of the following is halogen exchange reaction?

6. Which reagent will you use for the following reaction?

CH3CH2CH2CH3 → CH3CH2CH2CH2Cl + CH3CH2CHClCH3
(i) Cl2/UV light
(ii) NaCl + H2SO4
(iii) Cl2 gas in dark
(iv) Cl2 gas in the presence of iron in dark

7. Arrange the following compounds in the increasing order of their densities.

(i) (a) < (b) < (c) < (d)
(ii) (a) < (c) < (d) < (b)
(iii) (d) < (c) < (b) < (a)
(iv) (b) < (d) < (c) < (a)

8. Arrange the following compounds in increasing order of their boiling points.

(b) CH3CH2CH2CH2Br

(i) (b) < (a) < (c)
(ii) (a) < (b) < (c)
(iii) (c) < (a) < (b)
(iv) (c) < (b) < (a)

9. In which of the following molecules carbon atom marked with asterisk (*) is asymmetric?

(i) (a), (b), (c), (d)
(ii) (a), (b), (c)
(iii) (b), (c), (d)
(iv) (a), (c), (d)

10. Which of the following structures is enantiomeric with the molecule (A) given below :

11. Which of the following is an example of vic-dihalide?

(i) Dichloromethane
(ii) 1,2-dichloroethane
(iii) Ethylidene chloride
(iv) Allyl chloride

12. The position of –Br in the compound in CH3CH==CHC(Br)(CH3)2 can be classified as ____________.

(i) Allyl
(ii) Aryl
(iii) Vinyl
(iv)Secondary

13. Chlorobenzene is formed by reaction of chlorine with benzene in the presence of AlCl3. Which of the following species attacks the benzene ring in this reaction?

(i) Cl
(ii) Cl+
(iii) AlCl3
(iv) [AlCl4]

14. Ethylidene chloride is a/an ______________.

(i) vic-dihalide
(ii) gem-dihalide
(iii) allylic halide
(iv) vinylic halide

15. What is ‘A’ in the following reaction?

16. A primary alkyl halide would prefer to undergo _____________.

(i) SN1 reaction
(ii) SN2 reaction
(iii) α–Elimination
(iv) Racemisation

17. Which of the following alkyl halides will undergo SN1 reaction most readily?

(i) (CH3)3C—F
(ii) (CH3)3C—Cl
(iii) (CH3)3C—Br
(iv) (CH3)3C—I

18. Which is the correct IUPAC name for ?

(i) 1-Bromo-2-ethylpropane
(ii) 1-Bromo-2-ethyl-2-methylethane
(iii) 1-Bromo-2-methylbutane
(iv) 2-Methyl-1-bromobutane

19. What should be the correct IUPAC name for diethylbromomethane?

(i) 1-Bromo-1,1-diethylmethane
(ii) 3-Bromopentane
(iii) 1-Bromo-1-ethylpropane
(iv) 1-Bromopentane

20. The reaction of toluene with chlorine in the presence of iron and in the absence of light yields ____________.

21. Chloromethane on treatment with excess of ammonia yields mainly

(i) N, N-Dimethylmethanamine
(ii) N–methylmethanamine (CH3—NH—CH3)
(iii) Methanamine (CH3NH2)
(iv) Mixture containing all these in equal proportion

22. Molecules whose mirror image is non superimposable over them are known as chiral. Which of the following molecules is chiral in nature?

(i) 2-Bromobutane
(ii) 1-Bromobutane
(iii) 2-Bromopropane
(iv) 2-Bromopropan-2-ol

23. Reaction of C6H5CH2Br with aqueous sodium hydroxide follows ____________.

(i) SN1 mechanism
(ii) SN2 mechanism
(iii) Any of the above two depending upon the temperature of reaction
(iv) Saytzeff rule

24. Which of the carbon atoms present in the molecule given below are asymmetric?

(i) a, b, c, d
(ii) b, c
(iii) a, d
(iv) a, b, c

25. Which of the following compounds will give racemic mixture on nucleophilic substitution by OH ion?

(i) (a)
(ii) (a), (b), (c)
(iii) (b), (c)
(iv) (a), (c)

Note : In the questions 26 to 29 arrange the compounds in increasing order of rate of reaction towards nucleophilic substitution.

26.

(i) (a) < (b) < (c)
(ii) (c) < (b) < (a)
(iii) (a) < (c) < (b)
(iv) (c) < (a) < (b)

27.

(i) (a) < (b) < (c)
(ii) (a) < (c) < (b)
(iii) (c) < (b) < (a)
(iv) (b) < (c) < (a)

28.

(i) (c) < (b) < (a)
(ii) (b) < (c) < (a)
(iii) (a) < (c) < (b)
(iv) (a) < (b) < (c)

29.

(i) (a) < (b) < (c)
(ii) (b) < (a) < (c)
(iii) (c) < (b) < (a)
(iv) (a) < (c) < (b)

30. Which is the correct increasing order of boiling points of the following compounds?
1-Iodobutane, 1-Bromobutane, 1-Chlorobutane, Butane

(i) Butane < 1-Chlorobutane < 1-Bromobutane < 1-Iodobutane
(ii) 1-Iodobutane < 1-Bromobutane < 1-Chlorobutane < Butane
(iii) Butane < 1-Iodobutane < 1-Bromobutane < 1-Chlorobutane
(iv) Butane < 1-Chlorobutane < 1-Iodobutane < 1-Bromobutane

31. Which is the correct increasing order of boiling points of the following compounds?

1-Bromoethane, 1-Bromopropane, 1-Bromobutane, Bromobenzene

(i) Bromobenzene < 1-Bromobutane < 1-Bromopropane < 1-Bromoethane
(ii) Bromobenzene < 1-Bromoethane < 1-Bromopropane < 1-Bromobutane
(iii) 1-Bromopropane < 1-Bromobutane < 1-Bromoethane < Bromobenzene
(iv) 1-Bromoethane < 1-Bromopropane < 1-Bromobutane < Bromobenzene

II. Multiple Choice Questions (Type-II)

Note : In the following questions two or more options may be correct. Consider the following reaction and answer the questions no. 32–34.

32. Which of the statements are correct about above reaction?

(i) (a) and (e) both are nucleophiles.
(ii) In (c) carbon atom is sp3 hybridised.
(iii) In (c) carbon atom is sp2 hybridised.
(iv) (a) and (e) both are electrophiles.

33. Which of the following statements are correct about this reaction?

(i) The given reaction follows SN2 mechanism.
(ii) (b) and (d) have opposite configuration.
(iii) (b) and (d) have same configuration.
(iv) The given reaction follows SN1 mechanism.

34. Which of the following statements are correct about the reaction intermediate?

(i) Intermediate (c) is unstable because in this carbon is attached to 5 atoms.
(ii) Intermediate (c) is unstable because carbon atom is sp2 hybridised.
(iii) Intermediate (c) is stable because carbon atom is sp2 hybridised.
(iv) Intermediate (c) is less stable than the reactant (b).

Answer Q. No. 35 and 36 on the basis of the following reaction.

35. Which of the following statements are correct about the mechanism of this reaction?

(i) A carbocation will be formed as an intermediate in the reaction.
(ii) OH will attach the substrate (b) from one side and Cl will leave it simultaneously from other side.
(iii) An unstable intermediate will be formed in which OH and Cl will be attached by weak bonds.
(iv) Reaction proceeds through SN1 mechanism.

36. Which of the following statements are correct about the kinetics of this reaction?

(i) The rate of reaction depends on the concentration of only (b).
(ii) The rate of reaction depends on concentration of both (a) and (b).
(iii) Molecularity of reaction is one.
(iv) Molecularity of reaction is two.

37. Haloalkanes contain halogen atom (s) attached to the sp3 hybridised carbon atom of an alkyl group. Identify haloalkane from the following compounds.

(i) 2-Bromopentane
(ii) Vinyl chloride (chloroethene)
(iii) 2-chloroacetophenone
(iv) Trichloromethane

38. Ethylene chloride and ethylidene chloride are isomers. Identify the correct statements.

(i) Both the compounds form same product on treatment with alcoholic KOH.
(ii) Both the compounds form same product on treatment with aq.NaOH.
(iii) Both the compounds form same product on reduction.
(iv) Both the compounds are optically active.

39. Which of the following compounds are gem-dihalides?

(i) Ethylidene chloride
(ii) Ethylene dichloride
(iii) Methylene chloride
(iv) Benzyl chloride

40. Which of the following are secondary bromides?

(i) (CH3)2 CHBr
(ii) (CH3)3C CH2Br
(iii) CH3CH(Br)CH2CH3
(iv) (CH3)2CBrCH2CH3

41. Which of the following compounds can be classified as aryl halides?

(i) p-ClC6H4CH2CH(CH3)2
(ii) p-CH3CHCl(C6H4)CH2CH3
(iii) o-BrH2C-C6H4CH(CH3)CH2CH3
(iv) C6H5-Cl

42. Alkyl halides are prepared from alcohols by treating with

(i) HCl + ZnCl2
(ii) Red P + Br2
(iii) H2SO4 + KI
(iv) All the above

43. Alkyl fluorides are synthesised by heating an alkyl chloride/bromide in presence of ____________ or ____________.

(i) Ca F2
(ii) CoF2
(iii) Hg2F2
(iv) NaF

III. Short Answer Type

44. Aryl chlorides and bromides can be easily prepared by electrophilic substitution of arenes with chlorine and bromine respectively in the presence of Lewis acid catalysts. But why does preparation of aryl iodides requires
presence of an oxidising agent?

45. Out of o-and p-dibromobenzene which one has higher melting point and why?
46. Which of the compounds will react faster in SN1 reaction with the OH ion?
CH3— CH2— Cl or C6H5— CH2— Cl

47. Why iodoform has appreciable antiseptic property?
48. Haloarenes are less reactive than haloalkanes and haloalkenes. Explain.
49. Discuss the role of Lewis acids in the preparation of aryl bromides and chlorides in the dark.
50. Which of the following compounds (a) and (b) will not react with a mixture of NaBr and H2SO4. Explain why?

(a) CH3CH2CH2OH

51. Which of the products will be major product in the reaction given below? Explain.

CH3CH = CH2 + HI → CH3CH2CH2I + CH3CHICH3
(A)                  (B)

52. Why is the solubility of haloalkanes in water very low?
53. Draw other resonance structures related to the following structure and find out whether the functional group present in the molecule is ortho, para directing or meta directing.

54. Classify the following compounds as primary, secondary and tertiary halides.
(i) 1-Bromobut-2-ene (ii) 4-Bromopent-2-ene
(iii) 2-Bromo-2-methylpropane
55. Compound ‘A’ with molecular formula C4H9Br is treated with aq. KOH solution. The rate of this reaction depends upon the concentration of the compound ‘A’ only. When another optically active isomer ‘B’ of this compound was treated
with aq. KOH solution, the rate of reaction was found to be dependent on concentration of compound and KOH both.

(i) Write down the structural formula of both compounds ‘A’ and ‘B’.
(ii) Out of these two compounds, which one will be converted to the product with inverted configuration.

56. Write the structures and names of the compounds formed when compound ‘A’ with molecular formula, C7H8 is treated with Cl2 in the presence of FeCl3.

57. Identify the products A and B formed in the following reaction :
(a) CH3—CH2—CH==CH—CH3+HCl → A + B

58. Which of the following compounds will have the highest melting point and why?

59. Write down the structure and IUPAC name for neo-pentylbromide.
60. A hydrocarbon of molecular mass 72 g mol–1 gives a single monochloro derivative and two dichloro derivatives on photo chlorination. Give the structure of the hydrocarbon.
61. Name the alkene which will yield 1-chloro-1-methylcyclohexane by its reaction with HCl. Write the reactions involved.
62. Which of the following haloalkanes reacts with aqueous KOH most easily? Explain giving reason.

(i) 1-Bromobutane
(ii) 2-Bromobutane
(iii) 2-Bromo-2-methylpropane
(iv) 2-Chlorobutane

63. Why can aryl halides not be prepared by reaction of phenol with HCl in the presence of ZnCl2?
64. Which of the following compounds would undergo SN1 reaction faster and why?

65. Allyl chloride is hydrolysed more readily than n-propyl chloride. Why?
66. Why is it necessary to avoid even traces of moisture during the use of a Grignard reagent?
67. How do polar solvents help in the first step in SN1 mechanism?
68. Write a test to detect the presence of double bond in a molecule.
69. Diphenyls are potential threat to the environment. How are these produced from arylhalides?

70. What are the IUPAC names of the insecticide DDT and benzenehexachloride? Why is their use banned in India and other countries?
71. Elimination reactions (especially β-elimination) are as common as the nucleophilic substitution reaction in case of alkyl halides. Specify the reagents used in both cases.
72. How will you obtain monobromobenzene from aniline?
73. Aryl halides are extremely less reactive towards nucleophilic substitution. Predict and explain the order of reactivity of the following compounds towards nucleophilic substitution:

74. tert-Butylbromide reacts with aq. NaOH by SN1 mechanism while n-butylbromide reacts by SN2 mechanism. Why?
75. Predict the major product formed when HCl is added to isobutylene. Explain the mechanism involved.
76. Discuss the nature of C–X bond in the haloarenes.
77. How can you obtain iodoethane from ethanol when no other iodine containing reagent except NaI is available in the laboratory?
78. Cyanide ion acts as an ambident nucleophile. From which end it acts as a stronger nucleophile in aqueous medium? Give reason for your answer.

IV. Matching Type

Note : Match the items given in Column I and Column II in the following questions.

79. Match the the compounds given in Column I with the effects given in Column II.

Blood substituent

Column I Column II
(i) Chloramphenicol (a) Malaria
(ii) Thyroxine (b) Anaesthetic
(iii) Chloroquine (c) Typhoid fever
(iv) Chloroform (d) Goiter
(e)

80. Match the items of Column I and Column II.

Column I Column II
(i) SN1 reaction (a) vic-dibromides
(ii) Chemicals in fire extinguisher (b) gem-dihalides
(iii) Bromination of alkenes (c) Racemisation
(iv) Alkylidene halides (d) Saytzeff rule
(v) Elimination of HX from alkylhalide (e) Chlorobromocarbons

81. Match the structures of compounds given in Column I with the classes of compounds given in Column II.

82. Match the reactions given in Column I with the types of reactions given in Column II.

83. Match the structures given in Column I with the names in Column II.

84. Match the reactions given in Column I with the names given in Column II.

V. Assertion and Reason Type

Note : In the following questions a statement of assertion followed by a statement of reason is given. Choose the correct answer out of the following choices.

(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are wrong statements.
(iii) Assertion is correct but reason is wrong statement.
(iv) Assertion is wrong but reason is correct statement.
(v) Assertion and reason both are correct statements but reason is not correct explanation of assertion.

85. Assertion : Phosphorus chlorides (tri and penta) are preferred over thionyl chloride for the preparation of alkyl chlorides from alcohols.
Reason : Phosphorus chlorides give pure alkyl halides.

86. Assertion : The boiling points of alkyl halides decrease in the order :
RI > RBr > RCl > RF
Reason : The boiling points of alkyl chlorides, bromides and iodides are considerably higher than that of the hydrocarbon of comparable molecular mass.

87. Assertion : KCN reacts with methyl chloride to give methyl isocyanide
Reason : CN is an ambident nucleophile.

88. Assertion : tert-Butyl bromide undergoes Wurtz reaction to give 2, 2, 3, 3-tetramethylbutane.
Reason : In Wurtz reaction, alkyl halides react with sodium in dry ether to give hydrocarbon containing double the number of carbon atoms present in the halide.

89. Assertion : Presence of a nitro group at ortho or para position increases the reactivity of haloarenes towards nucleophilic substitution.
Reason : Nitro group, being an electron withdrawing group decreases the electron density over the benzene ring.

90. Assertion : In monohaloarenes, further electrophilic substitution occurs at ortho and para positions.
Reason : Halogen atom is a ring deactivator.

91. Assertion : Aryl iodides can be prepared by reaction of arenes with iodine in the presence of an oxidising agent.
Reason : Oxidising agent oxidises I2 into HI.

92. Assertion : It is difficult to replace chlorine by –OH in chlorobenzene in comparison to that in chloroethane.
Reason : Chlorine-carbon (C—Cl) bond in chlorobenzene has a partial double bond character due to resonance.

93. Assertion : Hydrolysis of (–)-2-bromooctane proceeds with inversion of configuration.
Reason : This reaction proceeds through the formation of a carbocation.

94. Assertion : Nitration of chlorobenzene leads to the formation of m-nitrochlorobenzene
Reason : —NO2 group is a m-directing group.

VI. Long Answer Type

95. Some alkylhalides undergo substitution whereas some undergo elimination reaction on treatment with bases. Discuss the structural features of alkyl halides with the help of examples which are responsible for this difference.

96. Some halogen containing compounds are useful in daily life. Some compounds of this class are responsible for exposure of flora and fauna to more and more of UV light which causes destruction to a great extent. Name the class of these halocompounds. In your opinion, what should be done to minimise harmful effects of these compounds.

97. Why are aryl halides less reactive towards nucleophilic substitution reactions than alkyl halides? How can we enhance the reactivity of aryl halides?

ANSWERS

I. Multiple Choice Questions (Type-I)

1. (ii)     2. (iv)     3. (i)     4. (ii)     5. (i)     6. (i)     7. (i)
8. (iii), boiling point of (a) 364 K. boiling point of (b) 375 K, boiling point of (c) 346 K
9. (ii)
10. (i), Hint : Make the models of all the molecules and superimpose (i) to (iv) molecules on molecule (A).
11. (ii)     12. (i)     13. (ii)     14. (ii)     15. (iii)     16. (ii)     17. (iv)     18. (iii)     19. (ii)     20. (iv)     21. (iii)     22. (i)

23. (i), Hint : is stable cation so favours the progress of reaction by SN1 mechanism.
24. (ii)     25. (i)     26. (iii)     27. (iv)     28. (iv)     29. (iii)     30. (i)     31. (iv)

II. Multiple Choice Questions (Type-II)

32. (i), (iii)     33. (i), (ii)     34. (i), (iv)     35. (i), (iv)     36. (i), (iii)     37. (i), (iv)     38. (i), (iii)     39. (i), (iii)     40. (i), (iii)     41. (i), (iv)     42. (i), (ii)     43. (ii), (iii)

III. Short Answer Type

44. Iodination reactions are reversible in nature. To carry out the reaction in the forward direction, HI formed during iodination is removed by oxidation. HIO4 is used as an oxidising agent.
45. p-Dibromobenzene has higher melting point than its o-isomer. It is due to symmetry of p-isomer which fits in crystal lattice better than the o-isomer.
46. C6H5—CH2—Cl

47. Due to liberation of free iodine.
48. See NCERT textbook for Class XII.
49. See NCERT textbook for Class XII.
50. (b), C—O bond is more stable in (b) because of resonance.

51. ‘B’ is major product of the reaction. For explanation, see Markownikov’s rule. Consult chemistry textbook, Class XI, NCERT, Section 13.3.5.
52. See NCERT textbook for Class XII.
53. Ortho-para directing due to increase in the electron density at ortho and para positions. (For resonance structures consult NCERT textbook, Class XII)
54. (i) Primary (ii) Secondary (iii) Tertiary

55. (i) Compound A : Compound B :
(ii) Compound ‘B’.

56.

57.

58. II, due to symmetry of para-positions; it fits into crystal lattice better than other isomers.

59.
; 1-Bromo-2,2-dimethylpropane

60. C5H12, pentane has molecular mass 72 g mol–1, i.e. the isomer of pentane which yields single monochloro derivative should have all the 12 hydrogens equivalent.

61.

62. (iii); The tertiary carbocation formed in the reaction is stable.
63. C—O bond in phenols is more stable due to resonance effect and it has double bond character, hence breaking of this bond is difficult.
64. (B) Undergoes SN1 reaction faster than (A) because in case of (B), the carbocation formed after the loss of Cl is stabilised by resonance, whereas, no such stabilisation is possible in the carbocation obtained from (A).
65. Allyl chloride shows high reactivity as the carbocation formed by hydrolysis is stabilised by resonance while no such stabilisation of carbocation exists in the case of n-propyl chloride.
66. Grignard reagents are highly reactive and react with water to give corresponding hydrocarbons.
RMgX + H2O → RH + Mg(OH)X
67. [Hint: solvation of carbocation.]
68. [Hint : (1) Unsaturation test with Br2 water (2) Bayer’s test.]
69. Consult NCERT textbook for Class XII.
70. Consult NCERT textbook for Class XII.
71. Consult NCERT textbook for Class XII.
72. Consult NCERT textbook for Class XII.
73. III > II > I
74. Consult Chemistry textbook (NCERT) Class XII, Part II.

75.

The mechanism involved in this reaction is:

76. Hint : Discuss polar nature and stabilisation of C—X bond.

77.

78. Hint : It acts as a stronger nucleophile from the carbon end because it will lead to the formation of C–C bond which is more stable than the C–N bond.

IV. Matching Type

79. (i) → (c) (ii) → (d) (iii) → (a) (iv) → (b)
80. (i) → (c) (ii) → (e) (iii) → (a) (iv) → (b) (v) →→ (d)
81. (i) → (b) (ii) → (d) (iii) → (a) (iv) → (c)
82. (i) → (b) (ii) → (d) (iii) → (e) (iv) → (a) (v) → (c)
83. (i) → (a) (ii) → (c) (iii) → (b) (iv) → (d)
84. (i) → (b) (ii) → (a) (iii) → (d) (iv) → (c)

V. Assertion and Reason Type

85. (ii) 86. (v) 87. (iv) 88. (i) 89. (i) 90. (v) 91. (iii) 92. (i) 93. (iii) 94. (iv)

VI. Long Answer Type

95. Hint : Primary alkyl halides prefer to undergo substitution reaction by SN2 mechanism whereas tertiary halides undergo elimination reaction due to the formation of stable carbocation.
96. Consult Chemistry textbook of NCERT for Class XII.
97. Consult Chemistry textbook of NCERT for Class XII.

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[ I suggest you see the videos starting with 1- first then starting with 2- ….. in that sequence. ]

[ Tell your friends about this link if you liked the videos ]

In case of doubts or suggestions, Please send me email at mokshya@gmail.com

search for videos in http://www.skmclasses.in

Answers to -> Frequently Asked Questions ( FAQ ) [ commonly asked intelligent Questions :-) ]

1 ) How do I prepare for IIT ?

Ans : – See the videos made by me ( search for videos in http://www.skmclasses.in
Though we have many more which have not been uploaded ). While watching the videos, take notes and try to solve the problems yourself by pausing the video. Tell me if any calculation is wrong. See the videos with 1- first then 2- and so on. Write to IAPT Kothrud, Pune office to buy ( 150 Rs approx ) the book with previous papers of NSEP ( National Standard Exam in Physics – The 1st level ), INPhO ( Indian National Physics Olympiad – 2nd level ). Prepare with these and see how much you are scoring. You can guess your ALL INDIA rank easily from NSEP, and INPhO rank. Since 1998 the IIT JEE toppers have been mostly representing India in IPhO.

2 ) Which codec and Player do I use to see the videos ?

Ans : – You can use GOM Player, or VLC Player. You have to have good speakers with filters or good earphones with filters. We have checked mostly it is OK with these. ( If you are depending only on your embedded speakers of computer /screen / keyboard then there may be extra distortions. As these speakers are often not of good Quality. Also install latest KL Codecs ) In any case reduce the volume see the board, imagine sitting in the last bench and solving the problems of your own. See if your solution differs anywhere with the scribbles on the board.

3 ) Why are you giving these ( high Quality ) lecture for free ?

Ans : Well there are lot of good things free in this world. Linux, My-SQL, Open-Office ….. Go to sourceforge and get thousands of high quality software free along with source code. Yes all officially free …. Why do you think Richard Stallman, Zimmerman, ….. etc are considered Guru philosophers ? In Punjab and Gurudwaras worldwide there are so many Langars where you get better food than Restaurants. ….. why ? Why do you have Dharmasalas and subsidized rest rooms near hospitals / Famous Temples / various places ? in Iftar party anyone can eat for free …. why ?

I am teaching since 1989 I have observed most students can do much better if they have the self motivation to solve and practice. Cheap books are available in second hand bookstalls, where you get thousands of Numericals to solve ….. but most students will like to blow their time going and coming for tuition, travel time …. TV for hours and hours watching cricket / Tennis games, playing computer games …. My free lectures are not going to make much difference in spending of unnecessary money for coaching ….. I know very well , how much people enjoy …. ! spending unnecessarily !!

-

Do you know that there are NO poor / needy students in Bangalore.
-

Sometime back I had tried to teach for IIT JEE FREE. Discussed with a few NGOs and social service guys. Arranged rooms but got only 1 student. We had informed many people in many ways to inform students …. We did not get students who are ready to learn for free. So I am sure these lectures are NOT FREE. If anyone learns from these, s/he changes and that’s the gain / benefit. This change ( due to learning ) is very costly …. Most do not want to learn ………..

search for videos in http://www.skmclasses.in
You will get most videos. I say most because I do not upload all videos that I make. I have many more videos which are not in the net.

:-)

4 ) How can I get all your lectures ?

Ans : – Apart from my lectures there are approx 700 GB of PCM ( Phy, Chem, Math ) lectures. It takes approx 3 years of continuous download from scattered sources. I have ( 20,000 )Thousands of these. You can take ALL of them from me in an external 1 TB hard disk, instead of spending so much money and time again for downloading. These cover ( by Various Professors ) everything of Chemistry, Physics, Maths… Lot of this is from outside India … as foreigners have much wider heart than Indians ( as most of GNU / open source software have been developed by Non-Indians ). I observed the gaps in these videos, and thus I am solving IIT, APhO, Roorkey, IPhO Numericals. Videos made by me along with these videos gives a complete preparation.

Send me a mail at mokshya@gmail.com to contact me.

search for videos in http://www.skmclasses.in
You will get most videos. I say most because I do not upload all videos that I make. I have many more videos which are not in the net.

:-)

5 ) How do you get benefited out of this ?

Ans :- If anyone learns we all will have better people in this world. I will have better “ YOU “.
:-)

6 ) Why do you call yourself a Zookeeper ?

Ans :- This is very nicely explained at http://zookeepersblog.wordpress.com/z00keeper-why-do-i-call-myself-a-zoookeeper/

:-)

7 ) Where do you stay ?

Ans :- Presently I am in Bangalore.

:-)

8 ) If I need videos in a few topics can you make them for me ?

Ans :- We actively answers doubts at doubtpoint.
see http://skmclasses.weebly.com/doubtpoint.html
In case you appreciate our time and efforts involved in answering complicated Questions, then get Quality answers at doubtpoint.

:-)

9 ) Why did you write an article saying there are No Poor students ?

Ans :- There are lots of NGOs and others working for rural / poor children education at lower classes. While very less effort is on for std 9 till 12. Also see the answer in question number ( 3 ) above. In more than 2 decades of teaching I never met a Poor child who was seriously interested in ( higher ) studies. As I have a mind / thinking of a ” Physicist “, I go by ” Experimental Observation “.

It is not about what is being said about poor in media / TV etc, or ” what it should be ” ( ? ) …. It is about what I see happening. Also to add ( confuse ? you more )…. You must be knowing that in several states over many years now girl students have better ( by marks as well as by pass percentage ) result in std 10 / Board Exams….. well but NEVER a girl student came FIRST in IIT JEE … why ? [ The best rank by a Girl student is mostly in 2 digits, very rarely in single digit ] ????? So ????

:-)

10 ) How much do I have to study to make it to IIT ?

Ans :- My experience of Teaching for IIT JEE since 1989, tells me, Total 200 hours per subject ( PCM ) is sufficient. If you see my Maths and Physics videos, each subject is more than 200 hours. So if someone sees all the videos diligently, takes notes and remembers, …… Done.

:-)

11 ) What is EAMCET ?

Ans :- Engineering Agriculture and Medicine Common Entrance Test is conducted by JNT University Hyderabad on behalf of APSCHE. This examination is the gateway for entry into various professional courses offered in Government/Private Colleges in Andhra Pradesh.

12 ) In your videos are you covering other Exams apart from IIT ?

Ans : – Yes. See many videos made by solving problems of MPPET, Rajasthan / J&K CET, UPSEAT ( UPES Engineering Aptitude Test ), MHCET, BCECE ( Bihar Combined Entrance Competitive Examination Board ), WB JEE etc

:-)

13 ) What is SCRA ?

Ans : – Special Class Railway Apprentice (SCRA) exam is conducted by Union Public Service Commission (UPSC) board, for about 10 seats.That translates into an astonishing ratio of 1 selection per 10,000 applicants. The SCRA scheme was started in 1927 by the British, to select a handful of most intelligent Indians to assist them in their Railway Operations, after training at their Railway’s largest workshop, i.e. Jamalpur Workshop, and for one year in United Kingdom. The selected candidates were required to appear in the Mechanical Engineering Degree Examination held by Engineering Council (London).

Thanks for your time. To become my friend in google+ ( search me as mokshya@gmail.com and send friend request )

Read http://edge.org/responses/what-scientific-concept-would-improve-everybodys-cognitive-toolkit
:-)
The following video is a must see for full CO2 cycle, plates of Earth, Geological activities, stability of weather

:-)
Article in Nature says CO2 increase is good for the trees

http://thegwpf.org/science-news/6086-co2-is-greening-the-planet-savannahs-soon-to-be-covered-by-forests.html

:-)

http://climaterealists.com/index.php?id=9752

BBC documentary Crescent and Cross shows the 1000 years of fight between Christians and Muslims. Millions have been killed in the name of Religion. To decided whose GOD is better, and which GOD to follow. The fight continues.
-

Summary of Women

:-)
The Virus of Faith

:-)
The God delusion

:-)
cassiopeia facts about evolution

-

Intermediate Fossil records shown and explained nicely Fossils, Genes, and Embryos http://www.youtube.com/watch?v=fdpMrE7BdHQ

The Rise Of Narcissism In Women

:-)
13 type of women whom you should never court

http://timesofindia.indiatimes.com/life-style/relationships/man-woman/13-Women-you-should-never-court/articleshow/14637014.cms

:-)
Media teaching Misandry in India http://www.youtube.com/watch?v=-M2txSbOPIo

Summary of problems with women

http://problemwithwomentoday.blogspot.in/2009/12/problem-with-women-today-what-in-hell.html

:-)
Eyeopener men ? women only exists
http://www.youtube.com/watch?v=6ZAuqkqxk9A

:-)

Most unfortunate for men

:-)

 

Each of you is an Activist in some way or other. You are trying to propagate those thoughts, ideas that you feel concerned / excited about.
-

Did you analyze your effectiveness ?

Culturomics can help you

:-D

see how biased women are. Experimental proof. Women are happy when they see another woman is beating a man ( see how women misbehave with men )

:-)
http://www.youtube.com/watch?v=LlFAd4YdQks

-

see detailed statistics at

An eye opener in Misandry

My sincere advice would be to be EXTREMELY careful ( and preferably away ) of girls. As girls age; statistically certain behavior in them has been observed. Most Male can NOT manage those behaviors… Domestic violence, divorce etc are rising very fast. Almost in all cases boys / males are HUGE loosers. Be extremely choosy ( and think from several angles ) before even talking to a girl.
:-)

http://zookeepersblog.wordpress.com/save-the-male/

:-)

How women manipulate men

http://www.angryharry.com/esWomenManipulateMen.htm

Gender Biased Laws in India

http://zookeepersblog.wordpress.com/biased-laws/

:-)

Only men are victimised

Men are BETTER than women

http://www.menarebetterthanwomen.com/

:-)

see http://www.youtube.com/watch?&v=T0xoKiH8JJM#!
:-)

Male Psychology http://www.youtube.com/watch?v=uwxgavf2xWE

Women are more violent than men

http://www.independent.co.uk/news/uk/home-news/women-are-more-violent-says-study-622388.html

:-)

In the year 2010, 168 men ended their lives everyday ( on average ). More husbands committed suicide than wives.
:-)

http://www.rediff.com/news/report/ncrb-stats-show-more-married-men-committing-suicide/20111028.htm

It is EXTREMELY unfortunate that media projects men as fools, women as superiors, Husbands as servants, and replaceable morons. In ad after ad worldwide from so many companies, similar msg to disintegrate the world is being bombarded. It is highly unacceptable misandry

:-)

It is NOT at all funny that media shows violence against MEN. Some advertisers are trying to create a new ” Socially acceptable culture ” of slapping Men ( by modern city women ). We ( all men ) take objection to these advertisements.
We oppose this Misandry bad culture. Please share to increase awareness against Men bashing

:-)

Are you a nice person ? Just shout Wooooooooo , Eyye Eyye and enjoy to see someone in trouble ….

-

Think what are you doing … why are you doing ?

Every Man must know this …

:-)
Manginas, White Knights, & Other Chivalrous Dogs

!
!
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……##### u r #####
……..### SWEET. ###
……/….#########…\
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(.(.(____)….`.#.´..(____).).)

 

 

key words

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bonded elements fixed ratio, usually chemical formula concentration amount solute mol IITJEE SKMClasses.weebly.com 1 dm 3 1000 cm solution coordinate bond shared pair electrons provided one bonding atoms called dative covalent bond covalent bond bond formed shared pair electrons cracking breaking long chained saturated hydrocarbonsIITJEE SKMClasses.weebly.com mixture shorter chained alkanesalkenes curly arrow symbol IITJEE SKMClasses.weebly.com reaction mechanisms IITJEE SKMClasses.weebly.com show movement electron Coaching ICWA Coaching CFA Coaching CFP Coaching CMAT Coaching School Tuitions CBSE School Tuitions Home Tuitions 9th STD Tuitions PUC Coaching 10th Std Tuitions College Tuitions Maths Tuitions Engineering Tuitions Accounts & Finance Tuitions MBA & BBA Coaching Microbiology & Biotech Tuitions Study Abroad GRE & SAT Coaching GMAT Coaching IELTS/TOEFL Coaching PTE Coaching proteins protonation pyridines pyrroles quinones quinolines radical reaction radicals rearrangement receptors reduction regioselectivity retro reaction rhodium ring closure ring contraction ring expansion ring opening ruthenium samarium scandium Schiff bases selenium self-assembly silicon sodium solid-phase synthesis solvent effects spectroscopy sphingolipids spiro compounds stereoselective synthesis stereoselectivity steric hindrance steroids Stille reaction substituent effects sulfates sulfonamides sulfones sulfoxides sulfur supported catalysis supramolecular tandem reaction tautomerism terpenoids thioacetals thiols tin titanium total synthesis transesterification transition metals transition states tungsten Umpolung vinylidene complexes vitamins Wacker reaction Wittig reaction ylides zeolites zinc BRST Quantization Effective field theories Field Theories Higher Dimensions Field Theories Lower Dimensions Large Extra Dimensions Lattice Quantum Field Theory Nonperturbative Effects Renormalization Group Renormalization Regularization skmclasses.weebly.com Renormalons Sigma Models 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products smaller enthalpy reactants, resulting heat loss IITJEE SKMClasses.weebly.com surroundings fractional distillation separation components liquid mixture skmclassesfractions IITJEE SKMClasses.weebly.com differ boiling point skmclasses.weebly.com hence chemical composition IITJEE SKMClasses.weebly.com distillation typically using fractionating column fragmentation process mass spectrometry IITJEE SKMClasses.weebly.com causes positive ion split skmclasses pieces one positive fragment ion functional group part organic molecule responsible skmclasses.weebly.com chemical reactions general formula simplest algebraic formula member homologous series. skmclasses.weebly.com example general formula alkanes giant covalent lattice dimensional structure atoms, bonded together strong covalent bonds giant ionic lattice three dimensional structure oppositely charged ions, bonded together strong ionic bonds giant metallic lattice three dimensional structure positive ions skmclasses.weebly.com delocalised electrons, bonded together strong metallic bonds greenhouse effect process IITJEE SKMClasses.weebly.com absorption subsequent emission infrared radiation atmospheric gases warms lower atmosphere planet’s surface group vertical column Periodic Table Elements group IITJEE SKMClasses.weebly.com similar chemical properties skmclasses.weebly.com atoms skmclasses.weebly.comnumber outer shell electrons Hess law reaction IITJEE SKMClasses.weebly.com one route skmclasses.weebly.com initial final conditions IITJEE SKMClasses.weebly.com skmclasses.weebly.com total enthalpy change skmclasses.weebly.com skmclasses.weebly.com route heterogeneous catalysis reaction IITJEE SKMClasses.weebly.com catalyst IITJEE skmclasses.weebly.com different physical state reactants; frequently, reactants IITJEE SKMClasses.weebly.com gases whilst catalyst solid heterolytic fission breaking covalent bond IITJEE SKMClasses.weebly.com both bonded electrons going IITJEE SKMClasses.weebly.com one atoms, forming cation (+ ion) skmclasses.weebly.com IITJEE SKMClasses.weebly.com anion ion homogeneous catalysis reaction catalyst skmclasses.weebly.com reactants physical state, IITJEE SKMClasses.weebly.com frequently aqueous gaseous state homologous series series organic compounds IITJEE SKMClasses.weebly.com skmclasses.weebly.com functional group, IITJEE SKMClasses.weebly.com successive member differing homolytic fission breaking covalent bond IITJEE SKMClasses.weebly.com one bonded electrons going IITJEE SKMClasses.weebly.com atom, forming two radicals hydrated Crystalline skmclasses.weebly.com containing water molecules hydrocarbon compound hydrogen skmclasses.weebly.com carbon hydrogen bond strong dipole attraction IITJEE SKMClasses.weebly.com electron deficient hydrogen atom (O H on different molecule hydrolysis reaction IITJEE SKMClasses.weebly.com water aqueous hydroxide ions IITJEE SKMClasses.weebly.com breaks chemical compound skmclasses two compounds initiation first step radical substitution IITJEE SKMClasses.weebly.com free radicals generated ultraviolet radiation intermolecular force attractive force IITJEE SKMClasses.weebly.com neighbouring molecules Intermolecular forces van der Waals’ forces induced dipole ces permanent dipole forces hydrogen bonds ion positively negatively charge atom covalently bonded group atoms molecular ion ionic bonding electrostatic attraction IITJEE SKMClasses.weebly.com oppositely charged ions first) ionisation energy IITJEE SKMClasses.weebly.com remove one electron IITJEE SKMClasses.weebly.com IITJEE SKMClasses.weebly.com ion one mole gaseous 1+ ions IITJEE SKMClasses.weebly.com IITJEE SKMClasses.weebly.com one mole gaseous 2+ ions second) ionisation energy IITJEE SKMClasses.weebly.com remove one electron IITJEE SKMClasses.weebly.com IITJEE SKMClasses.weebly.com ion one mole gaseous 1+ ions IITJEE SKMClasses.weebly.com IITJEE SKMClasses.weebly.com one mole gaseous 2+ ions successive ionisation measure energy IITJEE SKMClasses.weebly.com remove IITJEE SKMClasses.weebly.com electron Chemistry energy second ionisation energy energy IITJEE SKMClasses.weebly.com one electron IITJEE SKMClasses.weebly.com IITJEE SKMClasses.weebly.com ion one mole gaseous 1+ ions IITJEE SKMClasses.weebly.com one mole gaseous 2+ ions isotopes Atoms skmclasses.weebly.com element IITJEE SKMClasses.weebly.com different numbers neutrons different masses le Chatelier’s principle system dynamic equilibrium subjected change position equilibrium will shift minimise change limiting reagent substance chemical reaction IITJEE SKMClasses.weebly.com runs out first lone pair outer shell pair electrons IITJEE SKMClasses.weebly.com involved chemical bonding mass nucleon number particles protons aneutrons) nucleus mechanism sequence steps showing path taken electrons reaction metallic bond electrostatic attraction IITJEE SKMClasses.weebly.com positive metal ions adelocalised electrons molar mass substance units molar mass IITJEE SKMClasses.weebly.com molar volume IITJEE SKMClasses.weebly.com mole gas. units molar volume IITJEE SKMClasses.weebly.com dm room temperature skmclasses.weebly.com pressure molar volume approximately 24.0 substance containing IITJEE skmclasses.weebly.com many particles thereIITJEE SKMClasses.weebly.com carbon atoms exactly 12 g carbon isotope molecular formula number atoms IITJEE SKMClasses.weebly.com element molecule molecular ion M positive ion formed mass spectrometry IITJEE SKMClasses.weebly.com molecule loses electron molecule small group atoms held together covalent bonds monomer small molecule IITJEE SKMClasses.weebly.com combines IITJEE SKMClasses.weebly.com monomers polymer nomenclature system naming compounds nucleophile atom group atoms attracted electron deficient centre atom donates pair electrons covalent bond nucleophilic substitution type substitution reaction IITJEE SKMClasses.weebly.com nucleophile attracted electron deficient centre atom, IITJEE SKMClasses.weebly.com donates pair electrons IITJEE SKMClasses.weebly.com new covalent bond oxidation Loss electrons IITJEE SKMClasses.weebly.com increase oxidation number oxidation number measure number electrons IITJEE SKMClasses.weebly.com IITJEE SKMClasses.weebly.com atom uses bond IITJEE SKMClasses.weebly.com atoms another element. Oxidation numbers IITJEE SKMClasses.weebly.com derive d rules oxidising agent reagent IITJEE SKMClasses.weebly.com oxidises (takes electrons from) another species percentage yield period horizontal row elements Periodic Table Elements show trends properties across period periodicity regular periodic variation properties elements IITJEE SKMClasses.weebly.com atomic number position Periodic Table permanent dipole small charge difference across bond resulting IITJEE SKMClasses.weebly.com difference electronegativities bonded atoms permanent dipole dipole force attractive force IITJEE SKMClasses.weebly.com permanent dipoles neighbouring polar molecules pi bond (p bond reactive part double bond formed above skmclasses.weebly.com below plane bonded atoms sideways overlap p orbitalspolar covalent bond bond IITJEE SKMClasses.weebly.com permanent dipole polar molecule molecule IITJEE SKMClasses.weebly.com IITJEE SKMClasses.weebly.com overall dipole skmclasses account dipoles across bonds polymer long molecular chain built monomer units precipitation reaction formation solid solution during chemical reaction Precipitates IITJEE SKMClasses.weebly.com formed IITJEE SKMClasses.weebly.com two aqueous solutions IITJEE SKMClasses.weebly.com mixed together principal quantum number n number representing relative overall energy orbital IITJEE SKMClasses.weebly.com increases distance nucleus sets orbitals IITJEE SKMClasses.weebly.com value IITJEE skmclasses.weebly.com electron shells energy levels propagation two repeated radical substitution IITJEE SKMClasses.weebly.com build up products chain reaction radical species unpaired electron rate reaction change concentration reactant product redox reaction reaction IITJEE SKMClasses.weebly.com reduction skmclasses.weebly.com oxidation take IITJEE SKMClasses.weebly.com reducing agent reagent IITJEE SKMClasses.weebly.com reduces (adds electron to) species reduction Gain electrons decrease oxidation number yield actual amount mol product theoretical amount mol product Chemistry reflux continual boiling skmclasses.weebly.com condensing reaction mixture ensure IITJEE SKMClasses.weebly.com reaction IITJEE SKMClasses.weebly.com without contents flask boiling dry relative atomic mass weighted mean mass atom element compared one twelfth mass IITJEE SKMClasses.weebly.com atom carbon relative formula mass weighted mean mass formula unit compared IITJEE SKMClasses.weebly.com one twelfth mass atom carbon relative isotopic mass mass atom isotope compared IITJEE SKMClasses.weebly.com one twelfth mass atom carbon relative molecular mass weighted mean mass molecule compared twelfth mass atom carbon 12 repeat unit specific arrangement atom s IITJEE SKMClasses.weebly.com occurs structure over over again. Repeat units IITJEE SKMClasses.weebly.com included brackets outside IITJEE SKMClasses.weebly.com symbol n Salt chemical compound formed IITJEE SKMClasses.weebly.com IITJEE SKMClasses.weebly.com acid IITJEE SKMClasses.weebly.com H+ ion acid IITJEE skmclasses.weebly.com been replaced metal ion another positive ion such IITJEE skmclasses.weebly.com ammonium ion, NH saturated hydrocarbon IITJEE SKMClasses.weebly.com single bonds only shell group atomic orbitals IITJEE SKMClasses.weebly.com skmclasses.weebly.com principal quantum number known main energy level simple molecular lattice three dimensional structure molecules, bonded together weak intermolecular forces skeletal formula simplified organic formula, IITJEE SKMClasses.weebly.com hydrogen atoms removed alkyl chains, leaving carbon skeleton skmclasses.weebly.com associated functional groups species particle IITJEE SKMClasses.weebly.com part chemical reaction specific heat capacity, c energy IITJEE SKMClasses.weebly.com raise temperature 1 g substance 1 C spectator ions Ions present part chemical reaction standard conditions pressure 100 kPa 1 atmosphere stated temperature usually 298 K (25 °C), skmclasses.weebly.com concentration 1 mol dm reactions aqueous solutions standard enthalpies enthalpystandard solution solution known concentration Standard solutions normally IITJEE SKMClasses.weebly.com titrations IITJEE SKMClasses.weebly.com determine unknown information another substance Chemistry standard state physical state substance under standard conditions 100 kPa 1 atmosphere) skmclasses.weebly.com 298 K 25 C stereoisomers Compounds skmclasses.weebly.com structural formula IITJEE SKMClasses.weebly.com different arrangement atoms space stoichiometry molar relationship IITJEE SKMClasses.weebly.com relative quantities substances part reaction stratosphere second layer Earth’s atmosphere, containing ‘ozone layer’, about 10 km IITJEE SKMClasses.weebly.com 50 km above Earth’s surface structural formula formula showing minimal detail skmclasses.weebly.com arrangement atoms molecule structural isomers Molecules IITJEE SKMClasses.weebly.com skmclasses.weebly.com molecular formula different structural arrangements atoms subshell group skmclasses.weebly.com type atomic orbitals s, p, d f within shell substitution reaction reaction IITJEE SKMClasses.weebly.com atom group atoms replaced different atom group atoms termination step end radical substitution IITJEE SKMClasses.weebly.com two radicals combine IITJEE SKMClasses.weebly.com molecule thermal decomposition breaking chemical substance IITJEE SKMClasses.weebly.com heat skmclasses least two chemical substances troposphere lowest layer Earth’s atmosphere extending Earth’s surface about 7 km (above poles) about 20 km above tropics unsaturated hydrocarbon hydrocarbon containing carbon carbon multiple bonds van der Waals’ forces Very weak attractive forces IITJEE SKMClasses.weebly.com induced dipoles neighbouring molecules volatility ease IITJEE SKMClasses.weebly.com liquid turns skmclasses gas Volatility increases boiling point decreases water crystallisation Water molecules IITJEE SKMClasses.weebly.com IITJEE SKMClasses.weebly.com IITJEE SKMClasses.weebly.com essential part crystalline structure absolute zero – theoretical condition concerning system at zero Kelvin IITJEE SKMClasses.weebly.com system does IITJEE SKMClasses.weebly.com emit absorb energy (all atoms rest accuracy – how close value IITJEE SKMClasses.weebly.com actual true value IITJEE SKMClasses.weebly.com see precision acid compound that, IITJEE SKMClasses.weebly.com dissolved water pH less 7.0 compound IITJEE SKMClasses.weebly.com donates hydrogen ion acid anhydride compound IITJEE SKMClasses.weebly.com two acyl groups boundIITJEE SKMClasses.weebly.com single oxygen atom acid dissociation constant – IITJEE SKMClasses.weebly.com equilibrium constant skmclasses.weebly.com dissociation weak acid actinides – fifteen chemical elements IITJEE SKMClasses.weebly.com actinium (89) skmclasses.weebly.com lawrencium (103 activated complex – structure IITJEE SKMClasses.weebly.com forms because collisionIITJEE SKMClasses.weebly.com molecules new bondsvIITJEE SKMClasses.weebly.com formed activation energy – minimum energy IITJEE SKMClasses.weebly.com must be inputIITJEE SKMClasses.weebly.com chemical system activity series actual yield addition reaction – within organic chemistry, IITJEE SKMClasses.weebly.com two IITJEE SKMClasses.weebly.com molecules combineIITJEE SKMClasses.weebly.com IITJEE SKMClasses.weebly.com larger aeration mixing air skmclasses liquid solid alkali metals metals Group 1 on periodic table alkaline earth metals – metals Group 2 on periodic table allomer substance IITJEE SKMClasses.weebly.com hIITJEE skmclasses.weebly.comdifferent composition another skmclasses.weebly.comcrystalline structure allotropy elements IITJEE SKMClasses.weebly.com different structures skmclasses.weebly.com therefore different forms IITJEE skmclasses.weebly.com Carbon diamonds, graphite, skmclasses.weebly.com fullerene anion negatively charge ions anode – positive side dry cell battery cell aromaticity – chemical property conjugated rings IITJEE SKMClasses.weebly.com results unusual stability. See IITJEE SKMClasses.weebly.com benzene atom – chemical element IITJEE SKMClasses.weebly.com smallest form, skmclasses.weebly.com made up neutrons skmclasses.weebly.comprotons within nucleus skmclasses.weebly.comelectrons circling nucleus atomic mass unit atomic number number representing IITJEE SKMClasses.weebly.com element IITJEE SKMClasses.weebly.com corresponds IITJEE SKMClasses.weebly.com number protons within nucleus atomic orbital region IITJEE SKMClasses.weebly.com electron atom may be found atomic radius average atomic mass Avogadro’s law Avogadro’s number number particles mole substance ( 6.02×10^23 ) barometer deviceIITJEE SKMClasses.weebly.comIITJEE SKMClasses.weebly.com measure pressure atmosphere base substance IITJEE SKMClasses.weebly.com accepts proton skmclasses.weebly.com high pH; common example sodium hydroxide (NaOH biochemistry chemistry organisms boiling phase transition liquid vaporizing boiling point temperature IITJEE SKMClasses.weebly.com substance startsIITJEE SKMClasses.weebly.com boil boiling-point elevation process IITJEE SKMClasses.weebly.com boiling point elevated adding substance bond – attraction skmclasses.weebly.com repulsion IITJEE SKMClasses.weebly.com atoms skmclasses.weebly.com molecules IITJEE SKMClasses.weebly.com cornerstone Boyle’s law Brønsted-Lowrey acid chemical species IITJEE SKMClasses.weebly.com donates proton Brønsted–Lowry acid–base reaction Brønsted-Lowrey base – chemical species IITJEE SKMClasses.weebly.com accepts proton buffered solution – IITJEE SKMClasses.weebly.com aqueous solution consisting weak acid skmclasses.weebly.comits conjugate base weak base skmclasses.weebly.comits conjugate acid IITJEE SKMClasses.weebly.com resists changes pH IITJEE SKMClasses.weebly.com strong acids basesIITJEE SKMClasses.weebly.com added burette (IITJEE SKMClasses.weebly.com buret glasswareIITJEE SKMClasses.weebly.com dispense specific amounts liquid IITJEE SKMClasses.weebly.com precision necessary titration skmclasses.weebly.com resource dependent reactions example combustion catalyst chemical compoundIITJEE SKMClasses.weebly.comIITJEE SKMClasses.weebly.com change rate IITJEE SKMClasses.weebly.com speed up slow down reaction,IITJEE SKMClasses.weebly.com regenerated at end reaction cation – positively charged ion centrifuge equipmentIITJEE SKMClasses.weebly.comIITJEE SKMClasses.weebly.com separate substances based on density rotating tubes around centred axis cell potential force galvanic cell IITJEE SKMClasses.weebly.com pulls electron through reducing agentIITJEE SKMClasses.weebly.com oxidizing agent chemical Law certain rules IITJEE SKMClasses.weebly.com pertain IITJEE SKMClasses.weebly.com laws nature skmclasses.weebly.comchemistry – examples chemical reaction – change one IITJEE SKMClasses.weebly.com substances skmclassesanother multiple substances colloid mixture evenly dispersed substances such IITJEE skmclasses.weebly.comm milks combustion IITJEE SKMClasses.weebly.com exothermic reaction IITJEE SKMClasses.weebly.com oxidant skmclasses.weebly.comfuel IITJEE SKMClasses.weebly.com heat skmclasses.weebly.comoften light compound – substance IITJEE SKMClasses.weebly.com made up two IITJEE SKMClasses.weebly.com chemically bonded elements condensation phase changeIITJEE SKMClasses.weebly.com gasIITJEE SKMClasses.weebly.com liquid conductor material IITJEE SKMClasses.weebly.com allows electric flow IITJEE SKMClasses.weebly.com freely covalent bond – chemical bond IITJEE SKMClasses.weebly.com involves sharing electrons crystal solid IITJEE SKMClasses.weebly.com packed IITJEE SKMClasses.weebly.com ions, molecules atoms IITJEE SKMClasses.weebly.com orderly fashion cuvette glasswareIITJEE SKMClasses.weebly.com spectroscopic experiments. usually made plastic glass quartz skmclasses.weebly.comshould be IITJEE possible deionization removal ions, skmclasses.weebly.com water’s case mineral ions such IITJEE skmclasses.weebly.comsodium, iron skmclasses.weebly.comcalcium deliquescence substances IITJEE SKMClasses.weebly.com absorb water IITJEE SKMClasses.weebly.com atmosphereIITJEE SKMClasses.weebly.com liquid solutions deposition – settling particles within solution mixture dipole electric magnetic separation charge dipole moment – polarity polar covalent bond dissolution solvation – spread ions monosacharide double bond sharing two pairs electradodes Microcentrifuge Eppendorf tube IITJEE SKMClasses.weebly.com Coomassie Blue solution earth metal – see alkaline earth metal electrolyte solution IITJEE SKMClasses.weebly.com conducts certain amount current skmclasses.weebly.com split categorically IITJEE skmclasses.weebly.com weak skmclasses.weebly.comstrong electrolytes electrochemical cell using chemical reaction’s current electromotive force made electromagnetic radiation type wave IITJEE SKMClasses.weebly.com through vacuums IITJEE skmclasses.weebly.comwell IITJEE skmclasses.weebly.commaterial skmclasses.weebly.comclassified IITJEE 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skmclasses.weebly.comH entropy – amount energy IITJEE SKMClasses.weebly.com available skmclasses.weebly.com work closed thermodynamic system usually symbolized IITJEE skmclasses.weebly.com S enzyme – protein IITJEE SKMClasses.weebly.com speeds up catalyses reaction Empirical Formula – IITJEE SKMClasses.weebly.com called simplest formula gives simplest whole -number ratio atoms IITJEE SKMClasses.weebly.com element present compound eppendorf tube – generalized skmclasses.weebly.comtrademarked term skmclasses.weebly.com type tube; see microcentrifuge freezing – phase transitionIITJEE SKMClasses.weebly.com liquidIITJEE SKMClasses.weebly.com solid Faraday constant unit electrical charge widelyIITJEE SKMClasses.weebly.com electrochemistry skmclasses.weebly.comequalIITJEE SKMClasses.weebly.com ~ 96,500 coulombs represents 1 mol electrons, Avogadro number electrons: 6.022 × 1023 electrons. F = 96 485.339 9(24) C/mol Faraday’s law electrolysis two part law IITJEE SKMClasses.weebly.com Michael Faraday published about electrolysis mass substance altered at IITJEE SKMClasses.weebly.com electrode during electrolysis directly proportionalIITJEE SKMClasses.weebly.com quantity electricity transferred at IITJEE SKMClasses.weebly.com electrode mass IITJEE SKMClasses.weebly.com elemental material altered at IITJEE SKMClasses.weebly.com electrode directly proportionalIITJEE SKMClasses.weebly.com element’s equivalent weight frequency number cyclesIITJEE SKMClasses.weebly.com unit time. Unit: 1 hertz = 1 cycleIITJEE SKMClasses.weebly.com 1 second galvanic cell battery made up electrochemical IITJEE SKMClasses.weebly.com two different metals connected salt bridge gas particles container IITJEE SKMClasses.weebly.com no definite shape volume geochemistry – chemistry skmclasses.weebly.comchemical composition Earth Gibbs energy – value IITJEE SKMClasses.weebly.com indicates spontaneity reaction usually symbolized G Cavalier India, Kalyan Nagar halogens Group 7 Periodic Table skmclasses.weebly.comare non-metals heat energy transferredIITJEE SKMClasses.weebly.com one systemIITJEE SKMClasses.weebly.com another thermal interaction jodium – Latin name halogen element iodine Joule SI I.M.S. Learning Resources Pvt. Ltd., Jaya Nagar 4th Block unit energy, defined IITJEE skmclasses.weebly.com newton-meter indicator special compound addedIITJEE SKMClasses.weebly.com solution IITJEE SKMClasses.weebly.com changes color depending on acidity solution; different indicators Giraffe Coaching, Cunningham Road different colors effective pH ranges inorganic compound – compounds IITJEE SKMClasses.weebly.com contain carbon IITJEE SKMClasses.weebly.com exceptions main article inorganic chemistry part chemistry concerned IITJEE SKMClasses.weebly.com inorganic compounds International Union Pure skmclasses.weebly.comApplied Chemistry IUPAC insulator material IITJEE SKMClasses.weebly.com resists flow electric current ion molecule gained lost one IITJEE SKMClasses.weebly.com electron ionic bond electrostatic attractionIITJEE SKMClasses.weebly.com oppositely charged ions ionization breaking up compound skmclassesseparate ions Kinetics sub-field chemistry specializing reaction rates Kinetic energy energy IITJEE SKMClasses.weebly.com object IITJEE SKMClasses.weebly.com motion lanthanides Elements 57 through 71 lattice Unique arrangement atoms molecules crystalline liquid solid Laws thermodynamics liquid state matter IITJEE SKMClasses.weebly.com shape container light Portion electromagnetic spectrum IITJEE SKMClasses.weebly.com visibleIITJEE SKMClasses.weebly.com naked eye. 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Ambedkar Veedhi Dr. DVG Road Delhi Public School, South 11 K.M., kanakapura Road Konanakunte Post, Bangalore Dr. Raj Kumar Road Dr. TCM Royan Road Ejipura Electronic City Field Marshal Cariappa Road Frazer Town Ganapathi Nagar Gandhi Bazaar Gandhi Nagar Ganga Nagar Gangadhar Chetty Road Ganigarpet Garvebhavi Palya Gavipuram Extension Gayathri Nagar Geddala Halli Geddalahalli Giri Nagar Giri Nagar 1st Phase Giri Nagar 2nd Phase GM Palya Gokula Golf Course Road Gorgunte Palya Govindaraj Nagar Green Park Extension, Guddada Halli Gundopanth Street National Public School, Indiranagar 12 A Main HAL II Stage, Bangalore H.Siddaiah Road Haines Road HAL HAL 2nd Stage HAL 3rd Stage HAL Airport Road Hampi Nagar Hanumantha Nagar Hayes Road HBR Layout Hebbal Kempapura Hebbal Ring Road Hegde Nagar Heggana Halli Hennur Hesaraghatta HKP Road HMT Layout Hongasandra Hoody Horamavu Hosakere Halli photochemistry photooxidation piperidines polyanions polycations polycycles polymers Porphyrins prostaglandins 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Training iPhone Development Training Mobile Application Testing Training Mobile Gaming Training Mobile Application Development Training Oakridge International School Oakridge International School, Sarjapur Road, , Bangalore School of India, Bannerghatta, Bangalore Delhi Public School DPS North Campus, Yelahanka, Bangalore Jain International Residential School (JIRS), Jakkasandra Post, Bangalore Delhi Public School (DPS East), Sarjapur, Bangalore TREAMIS World School, Electronics City, Bangalore South Delhi Public School (South), Kanakapura Road, Bangalore The Deen’s Academy, Whitefield, Bangalore National Public School (NPS), Koramangala, Bangalore Royale Concorde International School, Kalyan Nagar, Bangalore Freedom International School, HSR Layout, Bangalore Air Force School Army Public School Bangalore Military School BGS International School Cambridge Public School Delhi Public School Deva Matha Central School Jain International Residential School Kendriya Vidyalaya A M C School A.S.C Public School Amara Jyothi Public School Anand Shiksha Kendra ICSE Syllabus ACTS Secondary School B Mona High School Baldwin Boys High School Baldwin Girls High School Bishop Cotton Boys School Bishop Cotton Girls School Brigade School Candor International School Cambridge Public School Cathedral High School Chinmaya Vidyalay Christ Academy Ekya School Gnan Srishti School of Excellence Gopalan National School India International School IIS Lawrence School-ICSE New Horizon Public School Notre Dame Academy Paradise Residential School Patel Public School Podar International School Prakriya Green Wisdom School Primus School Ryan International School Sishu Griha St. Francis De Sales (SFS) High School Sherwood High Sri Kumaran Childrens Home St Francis School St Johns High School St Thomas Public School St. Patricks Academy St. Peters School Vibgyor High CBSE Syllabus AECS Magnolia Maaruti Public School Amaatra Academy Amrita Vidyalayam BGS-NPS School Brigade School BRS Global Centre for Excellence Capitol Public School CMR National Public School Delhi Public School East, South, North Edify School EuroSchool Freedom International School Geethanjali Montessori Geethanjali Vidhyalaya Gitanjali International School GISB Greengrove International School Gomathy Global School Harvest International School JSS Public School Kendriya Vidyalaya KV Manipal Tattva School Mirambika School for New Age NITTE International School National Centre for Excellence NCFE National Public School New Horizon Gurukul NHG Oakridge International School Presidency School PSBB LLA Padma Seshadri Bal Bhavan Radcliffe School Ravindra Bharathi Global School Sadhguru Sainath International School SSI Sri Kumaran Childrens Home Sunrise International Residential School Sujaya School The Samhita Academy Vagdevi Vilas School Venkat International Public School VIPS Vyasa International School Zee School IGCSE Syllabus Asia Pacific World School Krupanidhi Cambridge International School Candor International School Ekya School Gitanjali International GISB Greengrove International School Gomathy Global School Gopalan International School Harvest International School India International School (IIS) Oakridge International School Primus School Shibumi Trio World School International Baccalaureate IB Candor International School Oakridge International School (IB-PYP) State Board Amaatra Academy Lawrence School-State Board Paradise Residential School Primus School St. Francis De Sales (SFS) High School Sri Kumaran Childrens Home St Francis School Vagdevi Vilas School Special Schools Sri Rakum School for the blind Mirambika School for New Age Sri Aurobindo Shibumi (J. Krishnamurthi Aurinko Academy Chetana Kini Institute Samarthanam Residential School XSeed Schools Mirambika School New Age Sri Aurobindo Mother Teresa Public School curriculum Chrysalis High List of Schools Achievers International Academy ACTS Secondary School Amaatra Academy Amar Jyothi School Amrita Vidyalayam Army Public School Asia Pacific World School Aurinko Academy B Mona High School Baldwin Boys High School Baldwin Girls High School Bangalore International School Bangalore School Bethany High Bethany Junior School BGS-NPS School Bishop Cotton Boys School Bishop Cotton Girls School Brigade School British International School BRS Global Centre for Excellence BVM Global Cambridge Public School Candor International School Capitol Public School Cathedral High School Chinmaya Vidyalaya Christ Academy Chrysalis High CMR National Public School Delhi Public School Deva Matha Central School Edify School Ekya School EuroSchool Freedom International School Gear School Geethanjali Montessori Geethanjali Vidhyalaya Gitanjali International (GISB) Global Indian International School Gnan Srishti School Gomathy Global School Gopalan School Green County Public School Greengrove International School Greenwood High Harvest International School India International School Innisfree House School JSS Public School Kendriya Vidyalaya (KV) Lawrence School ICSE Lawrence School-State Magnolia Maaruti Public School Manipal Tattva School Mirambika School for New Age Mother Teresa Public School National Centre for Excellence National Hill View Public School National Public School New Horizon Gurukul New Horizon Public School Nitte International School Notre Dame Academy Oakridge International School Oxford Public School Parachute Regiment School Paradise Residential School Patel Public School Podar International School Prakriya Green Wisdom School Presidency School Primus School PSBB LLA Radcliffe School Ravindra Bharathi Global School Ryan International School Sadhguru Sainath International School Samarthanam Residential School SFS High School Sherwood High Shibumi Silver Oaks Sishu Griha Sri Chaitanya Techno School Sri Kumaran Childrens Home Sri Rakum School for the blind St Francis School St Johns High School St Mira School St Thomas Public School St. Patrick’s Academy St. Peters School Sujaya School Sunrise International Residential School The Samhita Academy Trio World School Vagdevi Vilas School Venkat International Public School Vibgyor High Vidyaniketan School Vyasa International School Whitefield Global School Xseed Pre-School Zee School
Primary Years Programme Colegio Anglo Mexicano MEXICO Milgate Primary School, AUSTRALIA Diploma Programme Australian International School Indonesia Pejaten Campus INDONESIA Instituto Educativa Fiscomisional Celina Vivar Espinosa, ECUADOR Unidad Educativa Juan de Salinas, ECUADOR Primary Years Programme Academia Moderna Charter, UNITED STATES Beacon School BRAZIL Dr. Orlando Edreira Academy, School 26, UNITED STATES Westhill Institute Carpatos Elementary Campus, MEXICO Westhill Institute, S.C. MEXICO Middle Years Programme Cooper Academy, UNITED STATES European International School VIETNAM Mark Bills Middle School UNITED STATES Mount Washington School UNITED STATES UCSI International School MALAYSIA Diploma Programme Cass Technical High School, UNITED STATES Colegio Experimental Juan Montalvo, ECUADOR Colegio Miguel Moreno Ordoñez de Cuenca ECUADOR Colegio Nacional Ibarra ECUADOR Colegio Nacional Mariano Benítez ECUADOR Colegio Nacional Velasco Ibarra, ECUADOR Colegio Nacional Veracruz, ECUADOR Colegio Pedro Vicente Maldonado ECUADOR Colegio Técnico 12 de Febrero, ECUADOR Colegio Técnico Fiscomisional Ecuador Amazónico, ECUADOR Colegio de Bachillerato Limón ECUADOR King Fahd Academy Bonn GERMANY Saudi Schools Moscow RUSSIAN FEDERATION Unidad Educativa 17 de Julio ECUADOR Unidad Educativa 12 de Febrero ECUADOR Unidad Educativa Bernardo Valdivieso ECUADOR Unidad Educativa Dayuma ECUADOR Unidad Educativa Federico González Suárez ECUADOR Unidad Educativa Fiscomisional Fray Bartolomé de las Casas ECUADOR Unidad Educativa Fiscomisional Juan Pablo II ECUADOR Unidad Educativa Fiscomisional San José de Calasanz ECUADOR Unidad Educativa León Ruales ECUADOR Unidad Educativa Nacional Napo ECUADOR Unidad Educativa Temporal Camilo Gallegos Dominguez ECUADOR Unidad Educativa Temporal Manuel Córdova Galarza ECUADOR Primary Years Programme Campus International School, UNITED STATES Carl Hankey K-8 School UNITED STATES Christa McAuliffe Elementary School UNITED STATES Goethe International Charter School , UNITED STATES Hammond Eastside Elementary Magnet School, UNITED STATES Hawthorne Elementary School UNITED STATES Idlewild Elementary School, UNITED STATES J. Colin English Elementary UNITED STATES Jose de Escandon Elementary, UNITED STATES Lincoln Elementary School, UNITED STATES Qingdao Amerasia International School CHINA Roland Park K-8 Magnet School for International Studies, UNITED STATES Theodore Roosevelt Elementary School, UNITED STATES Woodrow Wilson Elementary UNITED STATES Middle Years Programme Cache La Poudre Middle School, UNITED STATES Carl Hankey K-8 School, UNITED STATES Cedar Shoals High School UNITED STATES Concord High School, UNITED STATES Harry Stone Montessori Academy, UNITED STATES International School of Monterey, UNITED STATES Johnnie R. Carr Middle School, UNITED STATES Prairie Seeds Academy, UNITED STATES Roland Park K-8 Magnet School, UNITED STATES Sterling Middle School UNITED STATES The Aga Khan Academy, Hyderabad, INDIA Diploma Programme Ausangate Bilingual School PERU Author’s School Istochnik RUSSIAN FEDERATION Colegio Fiscal Técnico El Chaco ECUADOR Colegio Juan Bautista Montini ECUADOR Colegio Nacional Ciudad de Cuenca ECUADOR Colegio Nacional Experimental Salcedo, ECUADOR Colegio Nacional Machachi, ECUADOR Colegio Nacional Mixto El Playon, ECUADOR Colegio Técnico Cascales, ECUADOR Dar al Marefa Private School, UNITED ARAB EMIRATES Escola Internacional del Camp SPAIN Gymnasium Jovan Jovanovic Zmaj SERBIA ISTEK Private Acibadem Schools TURKEY Instituto Superior Tecnológico Carlos Cisneros ECUADOR Instituto Superior Tecnológico Daniel Alvarez Burneo ECUADOR Instituto Técnico Superior Isabel de Godin ECUADOR King Abdulaziz Saudi School Rome ITALY Riga State Gymnasium Nr. 2 LATVIA Saudi School Vienna AUSTRIA State IS Seeheim Jugenheim/Schuldorf Bergstrasse GERMANY Unidad Educativa Bolívar, ECUADOR Unidad Educativa Abelardo Moncayo, ECUADOR Unidad Educativa Fiscomisional Verbo Divino, ECUADOR Unidad Educativa Mayor ECUADOR Unidad Educativa Nueva Semilla, ECUADOR Unidad Educativa Temporal Juan Bautista Vásquez, ECUADOR Primary Years Programme Ajman Academy UNITED ARAB EMIRATES British International School Kiev UKRAINE Cache La Poudre Elementary School, UNITED STATES Dr. Thomas S. O Connell Elementary School UNITED STATES Gems World Academy Abu Dhabi UNITED ARAB EMIRATES Hebron-Harman Elementary School, UNITED STATES International School of Solothurn, SWITZERLAND Lisa-Junior Primary School AUSTRIA Madison Richard Simis Elementary School, UNITED STATES Miina Härma Gümnaasium, ESTONIA Riffenburgh Elementary School UNITED STATES Roscoe Wilson Elementary School, UNITED STATES Singapore International School INDIA William H. Wharton K-8 Dual Language Academy UNITED STATES World Academy of Tirana, ALBANIA École Centrale, CANADA École Micheline-Brodeur CANADA École Saint-Édouard, CANADA École élémentaire catholique Jean-Paul II CANADA Özel Istanbul Coskun Koleji Anaokulu & Ilkokulu TURKEY Middle Years Programme Abraham Lincoln Middle School UNITED STATES Beijing Huijia Private School CHINA Cakir Middle School TURKEY Durango High School UNITED STATES Emirates IS Meadows, UNITED ARAB EMIRATES Madison International School, MEXICO Meadow Park Middle School, UNITED STATES North Central High School, UNITED STATES Phuket International Academy Day School THAILAND Ray Wiltsey Middle School UNITED STATES Rockridge Secondary School CANADA School Lane Charter School UNITED STATES Strothoff International School Rhein-Main Campus Dreieich GERMANY Tsukuba International School JAPAN École Père-Marquette, CANADA École secondaire Saint-Luc, CANADA Diploma Programme Anania Shirakatsy Armenian National Lyceum Ed’l Complex-CJSC, ARMENIA COLEGIO ALAUDA SPAIN Colegio Británico, MEXICO Colegio Nacional Camilo Gallegos Toledo ECUADOR Colegio Nacional Experimental Amazonas, ECUADOR Colegio Nacional Experimental María Angélica Idrobo, ECUADOR Colegio Nacional San José, ECUADOR Eastern Mediterranean International School, ISRAEL Emirates National School UNITED ARAB EMIRATES GEMS American Academy Abu Dhabi, UNITED ARAB EMIRATES German International School Sharjah UNITED ARAB EMIRATES Instituto Tecnológico Superior Angel Polibio Chaves, ECUADOR International School Moshi Arusha Campus TANZANIA, UNITED REPUBLIC OF International School of Bydgoszcz POLAND Ludoteca Elementary & High School, Padre Víctor Grados, ECUADOR Léman International School Chengdu CHINA Metropolitan School of Panama, PANAMA Munic. Atms. Educ. Institution Kogalym Secondary School ?8, RUSSIAN FEDERATION Phorms Bilingual Gymnasium, GERMANY Royal High School, UNITED STATES SIS Swiss International School Stuttgart-Fellbach, GERMANY Seedling Public School INDIA The British School of Beijing CHINA Unidad Educativa Fiscal Experimental del Milenio, ECUADOR Unidad Educativa Juan de Velasco ECUADOR Unidad Educativa Tumbaco, ECUADOR École secondaire Gaétan Gervais, CANADA École secondaire Hanmer CANADA Stonehill International School American School of Bombay Mumbai Day school offering PYP MYP DP Dhirubhai Ambani International School Mumbai Day school offering DP Ecole Mondiale World School, Mumbai Day school offering DP Jamnabai Narsee School Mumbai Day school offering DP Ahmedabad International School Ahmedabad Day School offering PYP Mahatma Gandhi International School Ahmedabad Day school offering MYP Mahindra United World College of India Pune Boarding school offering DP Mercedes-Benz International School Pune American Embassy School Delhi Day school offering DP The British School, Delhi Day school offering DP Pathways World School, Gurgaon Boarding school offering PYP DP SelaQui World School, Dehra Dun Boarding school offering DP Canadian International School, Bangalore Mixed Boarding Day school offering DP International School of Bangalore, Bangalore Mixed Boarding Day school offering DP Oakridge International School Hyderabad Day school offering PYP Chinmaya International Residential School Coimbatore Boarding school offering DP Good Shepherd International School Ooty Boarding school offering DP Kodaikanal International School, Kodaikanal Boarding school offering DP Home Tuition Group teachers available small groupsstudents IB International Baccalaureate Programme, IGCSE, ISc, ICSE, CBSE Schools offering IB ( International Baccalaureate ) Programme Bangalore International School Geddalahalli Hennur Bagalur Road Kothanur Post Bengaluru India 560 077 Stonehill International School, 1st Floor, Embassy Point #150, Infantry Road Bengaluru 560 001 Stonehill International School 259/333/334/335 Tarahunise Post Jala Hobli, Bengaluru North 562157 Candor International School Begur Koppa Road, Hullahalli Off Bannerghatta Road, Near Electronic City Bangalore 560105 Greenwood High International School Bengaluru, No.8-14, Chickkawadayarapura, Near Heggondahalli Gunjur Post, Varthur Sarjapur Road, Bangalore 560087 Sarla Birla Academy, Bannerghatta, Bangalore, Canadian International School, Yelahanka, Bangalore Indus International School Billapura Cross Sarjapur Bangalore

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