Chap-1-alkyl-halide-aryl-halide-exercise.pdf

ALLEN

CHEMISTRY ALLEN Study Package For – JEE (Advanced)

JEE-Chemistry EXERCISE-01

CHECK YOUR GRASP

SELECT THE CORRECT ALTERNATIVE (ONLY ONE CORRECT ANSWER)

H 1.

Cl

+ SOCl2  is-

H

H

(A)

(B) Cl

2.

OH

The product formed in the reaction

The reaction

HO

H

(C)

H

+ SOCl2

H

O Cl

N

H

SO3H

(D)

Cl + SO2 +

N+ Cl – H

proceeds by the mechanism (A) S N1 3.

(B) S N 2

1, 3- Dibromopropane reacts with metallic zinc to form (A) propene

4.

(D) S E 2

(C) SNi

(B) cyclopropane

(C) propane

(D) hexane

Consider the following reaction sequence, aq.H 2 SO 4 PCl 5   A   B. CH3C  CH  HgSO 4

Heat

The products (A) and (B) are, respectively, (B) CH 3CH 2 CHO and CH 3CH 2CHCl 2

(C) CH 3CHOHCH 3 and CH 3CHClCH 3

(D) CH 3CH 2 CH 2OH and CH 3 CH 2CH 2Cl

Which of the following has highest dipole moment: (A) CH 3Cl

6.

(B) CH 3F

(B) carbanion

(C) cabocation

(D) final product

(C) HCN

(D) NH 4CN

To form alkane isonitrile, alkyl halide is reacted with: (A) KCN

8.

(D) CH 3I

In S N1 the first step involves the formation of (A) free radical

7.

(C) CH 3Br

(B) AgCN

Which one of the following compounds most readily undergoes substitution by S N 2 mechanism ?

(B) H3C

(A) H3C

H3C

Cl

CH3 (C) H3C

(D)

C3H7

Cl

H3C

CH3 Cl

Cl 9.

Sec. Butyl chloride undergo alkaline hydrolysis in the polar solvent by (A) S N 2

(B) S N1

(C) S N1 and S N 2

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(D) none of these

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5.

(A) CH 3COCH 3 and CH 3CCl 2CH 3

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JEE-Chemistry 10.

Grignard reagent can be prepared by dry (A) CH 3 —CH 2—Cl + Mg  ether

dry (B) CH3 CH CH2 + Mg  ether

Cl

OH

CH3 dry (C) CH3 C OH + Mg  ether

(D) All of them

CH3 11.

Most stable carbocation formed from (CH 3) 3C–Br, (C 6H5) 3CBr,(C 6H 5) 2CHBr and C 6H5CH 2Br would be 



(A) C 6H 5 C H 2 12.

(C) (C 6H 5) 3 C

CH3 CH CH CH3

alc. KOH

CH2 (A) CH 3—CH

CH CH2 CH3

CH—CH 3 predominates

(B) CH 2

(C) Both are formed in equal amounts

15.

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17.

18.

20.

21.

(C) Ethyl alcohol

(D) Nitro ethane

The reaction ,CH3Br + OH–  CH3OH + Br–

obeys the mechanism

(A) S N1

(C) E1

(B) S N 2

(D) E2

Ethylidene chloride can be prepared by the reaction of HCl and (B) Ethylene

(C) Acetylene

(D) Ethylene glycol

1–phenyl–2–chloropropane on treating with alc. KOH gives mainly (A) 1–phenylpropene

(B) 2–phenylpropene

(C) 1–phenylpropane–2–ol

(D) 1–phenylpropan–1–ol

Grignard reagent is obtained when magnesium is treated with (A) Alkyl halide in presence of alcohol

(B) Alkyl halide in presence of phenol

(C) Alkyl halide in presence of dry ether

(D) Alkyl halide in presence of alcoholated ether

Ethylene reacts with bromine to form (A) Chloroethane

19.

(D) The product ratio depends on the halogen

(B) Ethene

(A) Ethane 16.

CH—CH 2 —CH 3 predominates

The products of reaction of alcoholic silver nitrite with ethyl bromide are (A) Ethane

14.

(D) (C 6H 5) 2 CH

For the reaction

CH 3 CH(X)CH 2CH 3

13.





(B) (CH3)3 C

(B) Ethylene dibromide

(C) Cyclohexane

(D) 1-bromo propane

Br2 KCN  X   Y ; Y is C2H4 

(A) CH 3CH 2CN

(B)

NC—CH 2 —CH 2 —CN

(C) Br—CH 2 —CH 2 CN

(D) Br—CH

CHCN

Reactivity order of halides for dehydrohalogenation is (A) R – F > R – Cl > R – Br > R – I

(B) R – I > R – Br > R – Cl > R – F

(C) R – I > R – Cl > R – Br > R – F

(D) R – F > R – I > R – Br > R – Cl

Which of the following is least reactive in a nucleophilic substitution reaction (A) CH 2

E ALLEN Materials

CHCl

(B) CH 3 CH 2 Cl

(C) CH 2

CHCH 2 Cl

(D) (CH 3) 3 C–Cl

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JEE-Chemistry 22.

The correct reactivity order of alcohols towards H–X will be

OH (I) CH 2

(II) H3C

CH—OH

(A) II > I > III > IV 23.

(III) CH 3—CH 2 —OH

CH2

OH

(B) IV > III > II > I

(C) II > IV > I > III

Al O

Cl

(B) CH3 CH CH2

OH OH

Cl

OH Cl

(C) CH3 CH CH2

Cl

(D) CH3 CH CH2

OH

Cl

Cl

For the reaction, ZnX 2 C2H5OH + HX    C2H5X,

(A) HI > HCl > HBr 25.

(D) II > IV > III > I

2 3 aq.NaOH HOCl   (Y)  Identify 'Z' in the following reaction series, CH3.CH2CH2Br   (X)   (Z) : Heat

(A) Mixture of CH3CH CH2 and CH3CH CH2

24.

(IV) CH3 CH CH3

the order of reactivity is

(B) HI > HBr > HCl

(C) HCl > HBr > HI

(D) HBr > HI > HCl

Ethyl alcohol reacts at a faster rate with HI than with HCl in forming the corresponding ethyl halides under identical conditions mainly because (A) HI, being a stronger acid, protonates ethyl alcohol at oxygen much better and helps substitution (B) the bond length in HI is much shorter than that in HCl (C) I– is a much better leaving group

ANSWER KEY

C HE C K Y OU R G R ASP Qu e.

1

2

3

4

5

6

7

8

9

E XE R CISE - 1 10

11

12

13

14

15

C

A

C

D

D

B

C

24

25

Ans .

B

B

B

A

A

C

B

B

Qu e.

16

17

18

19

20

21

22

23

Ans .

A

C

B

B

B

A

D

B

B

D

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(D) I– is a much better nucleophile than Cl–

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JEE-Chemistry EXERCISE–02

BRAIN TEASERS

SELECT THE CORRECT ALTERNATIVES (ONE OR MORE THEN ONE CORRECT ANSWERS) 1.

Which of the following does/do produce a white precipitate of AgCl on warming with alcoholic silver nitrate? (A) Allyl chloride

2.

(B) t-Butyl chloride

Cl

(I)

Cl

(II)

(A) I < II < III < IV

(III)

(B) IV < III < II < I

5.

(D) IV < II < I < III

The order of decreasing nucleophilicity of the following is (B) CH 3O– > OH – > CH 3COO – > H 2O (D) HO – > CH 3O –> CH 3COO –> H 2 O

The order of decreasing SN1 reactivities of the halides CH 3 CH 2 CH 2 Cl

CH 2 = CHCHClCH 3

CH 3 CH 2 CHClCH 3

I

II

III

(A) I > II > III

(B) II > I > III

(C) II > III > I

(D) III > II > I

Consider the following anions.

O

O

CF3–S–O–

O–

C6H5–S–O–

O (I)

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Cl (IV)

(C) IV < I < II < III

(A) H 2O > OH – > CH 3COO – > CH 3O – (C) CH3COO– > CH3O–> OH– > H2O 4.

(D) Vinyl chloride

What is the order of reactivity of the following compounds towards nucleophilic substitution?

Cl

3.

(C) Benzyl chloride

O (II)

(III)

O CH3–C–O– (IV)

When attached to sp3- hybridized carbon, their leaving group ability in nucleophilic substitution reactions decreases in the order (A) I > II > III > IV 6.

(B) I > II > IV > III –

–

(C) IV > I > II > III

(D) IV > III > II > I

–

The basicity of RO ,HO , RCOO , ROH, and H2O are of the order (A) HO– > RO– > H2O > ROH > RCOO– (B) RO– > HO– > RCOO– > ROH > H2O (C) H2O > ROH > RCOO– > HO– > RO– (D) ROH > H2O > HO– > RCOO– > RO–

7.

Which of the following are aprotic solvents : (A) DMSO

8.

(B) DMF

(C) H 2 O

(D) CH 3 COOH

Which is/are true statements (s) : (A) Protonation increases electrophilic nature of carbonyl group (B) CF3 SO 3– is better leaving group than CH 3 SO 3– (C) Benzyl carbonium ion is stabilised by resonance

OH (D) CCl 3 CH

E ALLEN Materials

is stable,due to H-Bonding

OH

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JEE-Chemistry Me 9.

SOCl2

 C—OH  inC 5 H 5 N

Ph

H Which statement is true for the above reaction ?

10.

(A) Retention of configuration

(B) Inversion of configuration

(C) Inversion and Retention both

(D) None

Which of the following undergoes hydrolysis most easily

Cl

Cl (A)

(C)

NO2 NO2 Cl

Cl

(C)

(D)

NO2 11.

NO2

NO2

NO2

A compound 'A' formula of C3H6Cl2 on reaction with alkali can give 'B' of formula C3H6O or 'C' of formula C3H4. 'B' on oxidation gave a compound of the formula C3H6O2. 'C' with dilute H2SO4 containing Hg2+ ion gave 'D' of formula C3H6O, which with bromine and alkali gave the sodium salt of C2H4O2. Then 'A' is (A) CH 3 CH 2CHCl 2

(C) CH 2ClCH 2CH 2Cl

Isobutyl magnesium bromide with dry ether and absolute alcohol gives (A) CH3 CH CH2OH and CH 3CH 2MgBr

(B) CH3 CH CH2 CH2

CH3 CH2

and Mg(OH)Br (D) CH3 CH CH3 and CH 3CH 2OMgBr

CH3

CH3 Following reaction is

H CH3(CH2)5

H 

OH C Br  HO C

(A) E1

15.

16.

(CH2)5CH3 CH3

H3C

14.

CH3 and Mg (OH) Br

CH3

(C) CH3 CH CH3 , CH2

13.

(D) CH 3 CHClCH 2Cl

(B) S N1

(D) S N 2

(C) E2

On treatment with chlorine in presence of sunlight, toluene gives the product (A) o-chloro toluene

(B) 2, 5-dichloro toluene

(C) p-chloro toluene

(D) Benzyl chloride

In S N1 reaction an optically active substrates mainly gives : (A) Retention in configuration

(B) Inversion in configuration

(C) Racemic product

(D) No product

Alkyl iodides can be prepared by :CCl 4 (A) RCH 2 COOAg + I 2  RCH 2 I 

acetone  RCH 2 I + NaCl (B) RCH 2 Cl +NaI  

(C) R—OH + HI  RI + H 2 O

(D) CH 4 + I 2  CH 3 I

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12.

(B) CH 3CCl 2CH 3

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JEE-Chemistry 17.

Which of the following reagents can be used to prepare an alkyl halide :(A) NaCl

18.

(B) HCl + ZnCl 2

(C) SOCl 2

(D) PCl 5

Which of the following reactions depict the nucleophilic substitution of C 2H 5Br :(A) C 2 H 5 Br + C 2 H 5 SNa  C 2 H 5 SC 2 H 5 + NaBr Na  C 2 H 5 OH  C 2 H 6 +HBr (B) C 2 H 5 Br 

(C) C 2 H 5 Br + AgCN  C 2 H 5 NC + AgBr (D) C 2 H 5 Br + KOH  C 2 H 5 OH+ KBr 19.

For an S N 2 reaction, which of the following statements are true :(A) The rate of reaction is independent of the concentration of the nucleophile (B) The nucleophile attacks the C-atom on the side of the molecule opposite to the group being displaced (C) The reaction proceeds with simultaneous bond formation and rupture (D) None of these

20.

Which of the following is an S N 2 reaction :(A) CH 3 CH 2 Br + KOH  CH 3 CH 2 OH + KBr (B) CH 3 CH 2 Br + CH 3 CH 2 ONa  CH 3 CH 2 OCH 2 CH 3 + NaBr (C) (CH 3 ) 3 CBr + KOH  (CH 3 ) 3 COH+ KBr

CH3

CH3 (D) CH3—CH2—C—Br + KOH

CH3CH2—C—OH + KBr CH3

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CH3

ANSWER KEY

B RAIN T EASER S

E XE R CISE - 2

Qu e.

1

2

3

4

5

6

7

8

9

10

11

12

13

14

15

Ans .

A ,B ,C

C

B

C

B

B

A ,B

A ,B ,C ,D

B

D

A

D

D

D

C

Qu e.

16

17

18

19

20

Ans .

B .C

B ,C ,D

A ,C ,D

B ,C

A ,B

E ALLEN Materials

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JEE-Chemistry

EXERCISE–03

MISCELLANEOUS TYPE QUESTIONS

TRUE OR FAL SE : 1.

Alkyl halides follow the reactivity sequence, R—I > R—Br > R—Cl > R—F

2.

Vinyl chloride reacts with dilute NaOH to form vinyl alcohol.

3.

Allyl chloride is more reactive than vinyl chloride.

4.

Tertiary butyl bromide undergoes S N1 reactions.

5.

Both vic- and gem-dihalides on heating with zinc dust in presence of alcohol form same alkene.

FILL IN THE BLANKS : 1.

The interaction of elemental sulphur with Grignard reagent gives ...................... .

2.

An alkyl halide may be converted into alcohol by ......................reaction

3.

Diethyl ether is obtained from ethyl bromide by treating it with ...................... and the name of the reaction is .................. .

4.

Allyl chloride is a ...................... compound while vinyl chloride is inert towards nucleophilic substitution.

5.

The dihalides in which halogen atoms are attached to adjacent carbon atoms are termed as............... .

6.

Alkyl halides are formed when thionyl chloride and ............... are refluxed in presence of pyridine.

7.

Ethylene chloride on hydrolysis with aq. KOH forms............... .

MATCH THE COLUMN Match the column I with column II. Column-I (react ion)

Cl C Ph (+) H

OH C + SOCl2 Ph (+) H

CH3 (A)

(B)

OH C + SOCl2 Ph (+) H

CH3

Column-II (Mechanism)

CH3

Pyridine

(p)

S N1

Cl (q) C H5C6 H (–)

S N2

CH3

–

(C)

(r)

SNi

(s)

E2

CH3

(D)

2.

OH Cl CH3 C +HCl  C H5C6 (+) H C6H5 (±) H CH3

Match the column I with column II. Column-I

Column-II

(Substrate)

(A)

(Relative rate of solvolysis in 50% aqueous ethanol at 45°C)

Cl

(B)

Cl

(p)

7700

(q)

1

(r)

91

(s)

1,30,000

H3C (C) (D)

H3C Ph

Cl Cl

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1.

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JEE-Chemistry ASSERTION & RE ASON QUESTION :

1.

These questions contains, Statement-I (assertion) and Statement-II (reason). (A) Statement-I is True, Statement-II is True ; Statement-II is a correct explanation for Statement-I (B) Statement-I is True, Statement-II is True ; Statement-II is NOT a correct explanation for Statement-I (C) Statement-I is True, Statement-II is False. (D) Statement-I is False, Statement-II is True. Statement-I : Iodination of akanes is carried out by heat in presence of readucing agent. Because Statement-II : Iodination of alkanes takepalce explosively.

2.

Statement-I : Chloropropane has higher boiling point than chloroethane. Because Statement-II : Haloalkanes are polar molecules.

3.

Statement-I : Polar solvent slows down S N

2

reaction.

Because Statement-II : CH 3 –Br is less reactive than CH 3 Cl. 4.

Statement-I : Primary benzylic halides are more reactive than primary alkyl halides towards S N 1 reaction. Because Statement-II : Reactivity depends upon the nature of the nucleophile and the solvent.

5.

Statement-I : Vinylic halides are reactive towards nucleophilic substitution reaction. Because Statement-II : Reactivity is due to the polarity of carbon-halogen bond.

6.

Statement-I : Ar yl halides undergo electrophilic substitution less readily than benzene. Because

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Statement-II : Ar yl halide gives only meta product w.r.t. electrophilic substitution. 7.

Statement-I : Optically active 2-iodibutane on treatment with NaI in acetone undergoes racemisation. Because Statement-II : Repeated Walden inversions on the reactant and its product eventually gives a racemic mixture.

8.

Statement-I : Free radical chlorination of n-butane gives 72% of 2-chlorobutane and 28% of 1-chlorobutane though it has six primary and four secondary hydrogens. Because Statement-II : A secondary hydrogen is abstracted more easily than the primary hydrogen.

9.

Statement-I : Nucleophilic substitution reaction on an optically active alkyl halide gives a mixture of enantiomers. Because Statement-II : The reaction occurs by S 1 mechanism. N

10.

Statement-I : Boiling point of alkyl halide increases with increasse in molecular weight. Because Statement-II : Boiling point of alkylhalides are in the order RI > RBr > RCI > RF.

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JEE-Chemistry COMPREHENSION BASED QUESTIONS : Comprehension # 1 An organic compound A has molecular formula C10H17Br and it is non-resolvable. A does not decolourize brown colour of bromine water solution. A on treatement with (CH 3) 2COK/(CH 3)3COH yields B as major product. B on treatment with H2/Pt yields (C10H16) which on treatment with Cl2/hv yields three monochloro derivative. Also B on boiling with acidic permanganate solution yields C(C 10 H 16 O 3 ). C on heating with sodalime yields D (C9H 16O). D on reducing with LiAlH4 followed by heating the product with concentrated H2 SO 4 yields E (C 9H 16) as major product. E on treatment with ozone followed by work-up with Zn–H 2 O yields 6-Ketononanal. Compound A is :

Br

Br (A)

2.

(C)

(D) none of these

(B)

(C)

(D)

Compound C is :

O

COOH

(A)

CH2 4.

(B)

Compound B is :

(A) 3.

Br

O

O

CH2 CH2

(B)

(C)

O

O O

(D)

H C=C

COOH CH2 H

Compound D is :

O

O (A)

O

(B)

(C)

CH3

(D)

CH3

COOH Comprehension # 2

Nucleophilic substitution reactions generally expressed as Nu – + R — L  R— Nu + L – Where Nu –  Nucleophile ; R—L  substrate ; L  leaving group The best leaving groups are those that become the most stable ions after they depart. Since most leaving groups leave as a negative ion, the best leaving groups are those ions that stabilize a negative charge most effectively. A good leaving group should be (a) electron-withdrawing to polarize the carbon (b) stable once it has left (not a strong base) (c) polarisable- to maintain partial bonding with the carbon in the transition state (both SN1 and SN2). This bonding helps to stabilise the transition state and reduces the activation energy.

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1.

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JEE-Chemistry 1.

Among the following which is feasible ? (A) X – + CH 3 —CH 2 —H  CH 3 —CH 2 —X + H – (B) X – + CH 3 —OH  CH 3 —X + OH  – (C) X + H3C —OH  CH 3 —X + H 2 O

H (D) X – + CH 3 —CH 3  CH 3 —X + CH 3 2.

Among the following which is false statement ? (A) The weaker the base after the group departs, the better the leaving group (B) A reactive leaving group would raise the energy of the product, driving the equilibrium towards the reactants (C) Relative leaving group ability may vary with change of solvent (D) Better leaving group only increases S N 2 rate, not S N 1.

3.

CH 3 Br

CH 3 F

CH 3 OH

CH 3 OSO 2 CF3

(I)

( II)

(III)

(IV )

The correct order of decreasing reactivity of the above compounds towards CH 3 O – in an S N 2 reaction is : (A) I > IV > II > III 4.

Cl – (I)

(B) IV > I > II > III

CH3O –

CH 3 S –

(II)

(II)

(C) IV > I > III > II

(D) IV > II > I > III

I– ( IV )

The correct order of increasing leaving group capability of above anoins

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(A) III < IV < II < I

(B) II < III < I < IV

(C) II < IV < III < I

(D) I < III < II < IV

Comprehension # 3 Nucleophilic aliphatic substitution reaction is mainly of two types : S N1 and S N2. The S N1 mechanism is a two step process. Reaction velocity of SN1 reaction depends only on the concentration of the substrate. Since product formation takes place by the formation of carbocation, optically active substrate gives (+) and (–) forms of the product. In most of the cases the product usually consits of 5-20% inverted product and 80-95% racemised species. The more stable the carbocation, the greater is the proportion of racemisation. In solvolysis reaction, the more nucleophilic the solvent, the greater is the proportion of inversion. 1.

Which one of the following compound will give S N1 reaction predominantly ?

CH3 (A) H5C6——–Br

CH3 2.

(B) H3C

(C) H3C—Br

(D) All of these

Br

Which of the following compounds will give S N1 and S N 2 reactions with considerable rate ?

CH3 I. C 6 H 5 —CH 2 —Br

II. CH 2 =CH—CH 2 —Br

III. CH 3 —CH(Br)CH 3

IV. H3C

CH3 Br Select the correct answer from the codes given below (A) I, II and III

E ALLEN Materials

(B) I, II and IV

(C) II, III and IV

(D) I, III and IV

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JEE-Chemistry 3.

For the given reaction

R1

R1 R——–X

HOH

R——–OH R2

R2

Which substrate will give maximum racemisation ?

H2C

CH3 (A) H5C6——–Br

Br

(B)

C2H5

C2H5

Br

Br —OCH3

H5C6——–

H5C6——–

(C)

+

ANSWER KEY

Tr u e / Fals e 1. T

2. F

3. T

4. T

Matc h

th e

2. nucleophilic substitution 5. vic-dihalides or alkylene halides



3. sodium ethoxide, williamson's synthesis 6. alcohols

C o lu m n

1. (A) r ; B q ; (C)  s ; (D) p 

5. F

F i ll i n t h e B lank s 1. thioalcohol 4. reactive 7. glycol



E XE R CISE - 3

2. (A) q ; (B) r ; (C)  s ; (D) p

A s s er ti o n - R eas o n Q u es ti o ns 1. D 8. A

2. B 9. A

C o mp rehe ns i o n

B as ed

3. C 10. B

4. B

5. D

Q u e st i o ns

C o mp re he ns i o n # 1 : 1. (A) C o mp re he ns i o n # 2 : 1. (C) C o mp re he ns i o n # 3 : 1. (A)

2. (C) 2. (D) 2. (A)

3. (A) 3. (B) 3. (C)

4. (C) 4. (B)

32 ALLEN Materials

Provided By - Material Point

6. C

7. A

\\node6\E_NODE6 (E)\Data\2014\Kota\JEE-Advanced\SMP\Che\Unit-11\Eng\1. Alkyl halide & Aryl halide\Exe.p65

NH3

M ISC EL L AN E OU S T YP E Q U EST ION



—NO2

(D)

CH3



CH3

E Available on Learnaf.com

JEE-Chemistry

EXERCISE–04 [A] 1.

CONCEPTUAL SUBJECTIVE EXERCISE

Arrange the following compounds in order of : Decreasing S N 1 reaction rate :

Ph

Ph

Ph

2.

Cl

Cl (II)

Cl (I)

Cl (IV)

(III)

Select the member of each pair that shows faster rate of S N 2 reaction with KI in acetone. (a) CH 3–CH 2–CH 2 –CH 2–Cl

and

CH3–CH–CH2–Cl CH3

(I)

(II)

(b) CH 3–CH 2–CH 2 –Cl

and

CH 3–CH 2–CH 2 –Br

(I)

(II)

CH3 (c) CH3–CH–CH2–CH2–Cl

and

CH3–C–CH2Cl CH3

CH3

(I)

(II) Br

(d)

CH3

CH3—CH2—CH2—CH—CH3 and CH3—CH—CH2—CH—CH3

(I) \\node6\E_NODE6 (E)\Data\2014\Kota\JEE-Advanced\SMP\Che\Unit-11\Eng\1. Alkyl halide & Aryl halide\Exe.p65

3.

Br

(II)

Of the following statements which are true for S N1 reaction. (a) Tertiary alkyl halides react faster than secondary. (b) The absolute confuguration of the product is opposite to that of the reactant when an optical active substrate is used. (c)

The reaction shows first order kinetics.

(d) The rate of reaction depends markedly on the nucleophilicity of the nucleophile. (e) The mechanism is two step. (f)

Carbocations are intermediate.

(g) Rate  [Alkyl halides] (h) The rate of the raction depends on the nature of the leaving group. 4.

Of the following statements, which are true for SN2 reaction. (a) Tertiary alkyl halides reacts faster than secondary. (b) The absolute configuration of product is opposite to that of the reactant when an optically active substrate is used. (c)

The reaction shows first order kinetics.

(d) The rate of the reaction depends markedly on the nucleophilicity of the attacking reagent. (e) The mechanism is one step.

E ALLEN Materials

33 Provided By - Material Point

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JEE-Chemistry (f)

Carbocations are intermediate.

(g) Rate  [Alkyl halides] (h) The rate of the raction depends on the nature of the leaving group. 5.

Arrange the isomers of molecular formula C4H9Cl in order of decreasing rate of reaction with sodium iodide in acetone.

6.

There is an overall 29-fold difference in reactivity of 1-chlorohexane, 2-chlorohexane towards potassium iodide in acetone. Which one is the most reactive ? why ?

CH2CH = CH2 7.

Identify the product when A reacts with

(A) (a) Br 2 /Fe

(b) Br 2/CCl 4

(c) NBS

(d) HBr –

8.

OH Identify major product in the following : ClCH 2CHCl 2  CH 2=CCl 2

EtO–

(a) CH3CH2CHCH3

(b) CH 3 CH 2 CH 2CH 2Br EtO–

Br

CH2CH2CHCH3 (c)

EtO–

CH3 (d) H3CCCH2CH2Br

Br

(CH3)3COK (CH3)3COH

CH3

CH2Cl

9.

Which is faster in the following pairs of halogen compounds undergoing S N2 reactions? (a)

Cl

and

(b)

Cl

I

and

Cl (c) 10.

Cl

Br

and

(d)

Br

and

Cl R – Mg – Br (A) on reaction with H2O forms a gas (B), which occupied 1.4 L/g at NTP. What is product

when R – Br reacts with benzene in presence of AlCl 3 ?

34 ALLEN Materials

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EtO– EtOH

(e)

E Available on Learnaf.com

JEE-Chemistry ANSWER KEY

C ON C EP T UAL SU BJ EC T IVE E X ER C ISE

1.

E XE R CISE - 4 (A)

IV > I > II > III

2.

(a) I (b) II (c) I (d) I

3.

(a) T (b) F (c) T (d) F (e) T (f) T (g) T (h) T

4.

(a) F (b) T (c) F (d) T (e) T (f) F (g) F (h) T

5.

1° > 2° > 3° Anion of acetic acid is more stabilised by resonance than phenoxide ion.

6.

1-chlorohexane Because it follows Sn2 path.

CH2CH = CH2 7.

and para

(a)

Br Ortho Br

CHCH= CH2

CH2CHCH2 (b)

(c)

Br

Br

CHCH2CH3 (d)

Br –

(1, 2-H shift gives more stable benzylic carbocation)

\\node6\E_NODE6 (E)\Data\2014\Kota\JEE-Advanced\SMP\Che\Unit-11\Eng\1. Alkyl halide & Aryl halide\Exe.p65

CH=CHCH2CH3 8.

(a) CH 3 CH = CHCH 3

(b) CH 3 CH = CHCH 3

(c)

CH3 CH3 (d) H3CCCH= CH2 9.

(e)

CH3 Ease of backside attack (less steric hindrance) decides which undergoes S N2 faster (except in (b) in which iodide is better leaving group). In all cases first one is fater than the other for S N2 reaction.

10.

Gas B is CH 4 , hence A is CH 3MgBr. CH 3Br forms

E ALLEN Materials

CH3 on reaction with benzene.

35 Provided By - Material Point

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JEE-Chemistry

EXERCISE–04 [B] 1.

BRAIN STORMING SUBJECTIVE EXERCISE

Explain the following observations: –

(a) Azide ion (N 3 ) react with 2- bromopentane thousand times faster than with neopentyl bromide in a S N2 reaction though former is a secondar y halide while latter is primary. (b) What will happen to the stereochemistry of product of the following reaction:\

Br CH3 + N 3 –

H

SN2

D (c) What will happen to the rate if the concentration of alkyl bromide in (b) is doubled? (d) What will happen to the rate if the concentration of azide ion in (b) is doubled? (e) How the sign of optical rotation of reactant and product are related in (b) (f) When allowed to stand in dilute H 2SO 4, laevo-rotatory 2-butanol slowly loses optical activity. Provide structure of major product in the following reaction indicating stereochemistry where appropriate:

D OH TsCl

C

(a)

CH3

3.

D

NaCN

CH3

H

H

OH HBr Heat

NaCN

Propose mechanism of the following reactions:

Cl (a)

O O

+ CH3O–

–

O

Br CH3O

(b)

(c)

O

CH3OH

O

4.

C

(b)

O

O

O

+ HO –

OH O

HO

Which of the following alkyl halide could be successfully used to synthesize Grignard reagent and why other fail?

Br N

HO (I)

Br (II)

O H2N

OH

Br

Br (IV)

(III)

36 ALLEN Materials

Provided By - Material Point

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2.

E Available on Learnaf.com

JEE-Chemistry 5.

An alkyl bromide A has molecular formula C 8H 17Br and four different structures can be drawn for it, all optically active. A on refluxing with ethanolic KOH solution yields only one elimination product B(C 8H 16) which is still enantiomeric. B on treatment with H 2/Pt yields C(C 8H 18) which does not rotate the plane polarized light, B on ozonolysis followed by work-up with H 2O 2 yields D(C 7H 14O) as one product which is still resolvable. Deduce structures of A to D.

6.

Identify A to G in the following.

Br2CCl4

(a)

O

(b)

7.

Br

Br2CCl4

Cl

KCN

A

KCN

D

Mg/ether

B

H3O+

B

H3O+

E

D2O

C

C

G

Na/ether

D

(A) + HCHO/HO 3

Na/ether (with two mol of A)

F Identify B to F 8.

Vinyl chloride does not give S N reaction but allyl chloride gives. Explain.

9.

Arrange the following in the increasing order of their ability as a leaving group: (a) CH3S–, CH3O–, CF3– and F– (b) CF 3SO 3–, CH 3SO 3– and CH 3COO –

\\node6\E_NODE6 (E)\Data\2014\Kota\JEE-Advanced\SMP\Che\Unit-11\Eng\1. Alkyl halide & Aryl halide\Exe.p65

10.

RBr when treated with AgCN in a highly polar solvent gives RNC whereas when it is treated with NaCN it gives RCN. Explain.

E ALLEN Materials

37 Provided By - Material Point

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JEE-Chemistry ANSWER KEY

B RAIN STOR MIN G SUB J EC T IVE E X ER C ISE

1.

E XE R CISE - 4 (B )

(a) Though neopentylbromide is primary, bulky tertiary butyl group possess very large steric hindrance –

to the attack of bulky nucleophile N 3 .

N3

Br

SN2

CH3 + N 3–

(b) H

CH3

H

D

D

(c) Rate will double

(d) Rate will double

(e) not related

(f) Recemization occur through carbocation intermediate

D 2.

(a)

D

C

C

(b)

CH3

NC

H3C

H

D

(a)

CH3

NC

H

H

O–

Cl 3.

C

CN +

O

– + OCH3

O + Cl –

O

O Cl

– + OCH3

OCH3

Br O–

O

O

–

–Br

O

– O

O – + OH

(c)

OCH3

– O – O

HO

HO

O Product 4.

O–

O

H2O

O

HO

Only II can be used for successful synthesis of Grignard reagent, rest all contain acidic proton and will react with R – (from Grignard reagent) forming alkane.

Br O

5.

A

C

B

Br 6.

D

CN

(A)

(B)

CN

Br

38 ALLEN Materials

Provided By - Material Point

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(b) Br

E Available on Learnaf.com

JEE-Chemistry O

O

COOH

CN

Br

(C)

(D)

(E)

COOH

Br

O

CN

O COOH

(F)

(G)

COOH

COOH

(decarboxylation takes place on heating when there is a keto group at - position) 7.

(B) Cl

D

(E) Cl

D

(D) D

Cl

CH2OH

(F) Cl

In Vinyl chloride, C – Cl bond is stable due to resonance (as in chlorobenzene)

CH2

CH

+

••

••

8.

(C) Cl

Mg– Br

Cl

CH2

••

CH

Cl

Hence SN reaction in which Cl is replaced by nucleophile is not possible. In addition to this, sp2- hybridised carbon is more acidic than sp3- carbon, hence removal of proton (H+) is easier than removal of halide (Cl–) In allyl chloride, S N reaction is easier since allyl carbocation formed after removal of Cl – is stabilised by resonance. + \\node6\E_NODE6 (E)\Data\2014\Kota\JEE-Advanced\SMP\Che\Unit-11\Eng\1. Alkyl halide & Aryl halide\Exe.p65

CH2

CH2

CHCH2Cl

CHCH2+Cl–

Allyl carbocation +

CH2 –

+

CH2

CH –

CH2 –

;

CH

CH2

(b) CH3COO– < CH3SO3– < CF3SO3–

9.

(a) CF3 < CH3O < CH3S

10.

As [CN] – is an ambident nuicleophile which ahve two nucleophile which have two nucleophilic sites and can attack from either side. In a highly polar solvent, AgCN promotes the formation of carbocation R + , precipitation of AgBr. ••

N •• R—BR + Ag + [CN – ] C

C

••

N ••

••

fast

 R–N+ C R+ + CN– + Ag Br  

–

slow

In the absence of such promotion by Ag +, with Na+[CN] –, the resulting S N2 reaction is found to proceed with preferential attack on the atom in the nucleophile which is more polarisable i.e. C. –  NC – +R – Br  [NC ....R....Br ]  N  C – R + Br –

E ALLEN Materials

Transition State

39 Provided By - Material Point

Available on Learnaf.com

JEE-Chemistry

EXERCISE–05 1.

2.

PREVIOUS YEARS QUESTIONS

Chlorination of toluene in the presence of light and heat followed by treatment with aqueous NaOH gives(A) o-cresol

(B) p-cresol

(C) 2, 4 dihydroxytoluene

(D) Benzoic acid

Aryl halides are less reactive towards nucleophilic substitution reaction as compared to alkyl halides due to(A) The formation of less stable carbonium ion (C) The inductive effect

3.

(D)

sp 2

[IIT - 90]

hybridised carbon attached to the halogen

(B) 1–butanol

[IIT - 91]

(C) 2–butene

(D) 2–butanol

In the addition of HBr to propene in the absence of peroxides, the first step involves the addition of (A) H +

5.

(B) Resonance stabilization

1-Chlorobutane on reaction with alcoholic potash gives (A) 1–butene

4.

[IIT - 90]

(C) H

(B) Br –

(D) Br 

[IIT - 93]

Arrange the following compounds in order of increasing dipole moment :

[IIT - 96]

(I) Toluene ; (II) m-dichlorobenzene ; (III) o-dichlorobenzene ; (IV) p-dichlorobenzene (A) I < IV < II < III

13.

15.

(D) (CH3) 3OD

+

(B) CH3CHCH3

[IIT - 97]

(D) CH3CHCH 2 2

(C) CH3CHCH2

(B) 3

(C) 4

(D) 1

(B) 1-butene

(C) cis-2-butene

[IIT - 97]

(D) trans-2-butene

(B) SOCl 2

(C) PCl5

[IIT - 98]

(D) NaOCl

(A) is ortho and para directing

(B) is meta directing

(C) deactivates the ring by hyperconjugation

(D) deactivates the ring

[IIT - 99]

A solution of (+) 2–chloro–2phenylethane in toluene racemises slowly in the presence of small amount of SbCl 5 due to the formation of [IIT - 99] (B) Carbene

(C) Free-radical

(D) Carbocation

The order of reactivity of the following alkyl halides for a S N 2 reaction is -

[IIT-2000]

(A) RF > RCl > R –Br > R–I

(B) R–F > R –Br > R–Cl > R–I

(C) R–Cl > R –Br > R–F > R–I

(D) R–I > R –Br > R–Cl > R–F

Which of the following has the highest nucleophilicity : (A)

16.

(C) (CD3) 3CD

Toluene, when treated with Br 2/Fe, gives o and p-bromotoluene, because the CH 3 group -

(A) Carbanion 14.

(B) (CH3)3OD

Benzyl chloride (C 6H 5CH 2Cl) can be prepared from toluene by chlorination with (A) SO2Cl2

12.

II T - 9 7]

During debromination of meso-2,3-dibromobutane, with Zn dust/CH3COOH the major compound formed is [IIT - 97] (A) n-butane

11.

(D) p-chloroaniline

The number of possible enantiomeric pairs that can be produced during monochlorination of isopentane(A) 2

10.

(C) m-chloroaniline

The intermediate during the addition of HCl to propene in presence of peroxide is (A) CH3CHCH2Cl

9.

(B) m-toluidine

[IIT - 97]

(CH3) 3CMgCl reaction with D 2O produces : (A) (CH3)3CD

8.

(D) IV < II < I < III

In the reaction of p-chloro toluene with KNH 2 in liq. NH 3, the major product is (A) o-toluidine

7.

(C) I < IV < II < III

F–

(B)

OH –

(C) CH3

[IIT-2000] –

(D) NH 2

An S N 2 reaction at an asymmetric carbon of a compound always gives :

–

[IIT-2001]

(A) an enantiomer of the substrate

(B) a product with opposite optical rotation

(C) a mixture of diastereomers

(D) a single stereoisomer

40 ALLEN Materials

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6.

(B) IV < I < II < III

E Available on Learnaf.com

JEE-Chemistry 17.

The number of isomer for the compound with molecular formula C 2BrCl FI is (A) 3

18.

(B) 4

(C) 5

[IIT - 01]

(D) 6

In the presence of peroxide, hydrogen chloride and hydrogen iodide do not give anti-Markovnikov's addition to alkenes because :

[IIT-01]

(A) both are highly ionic (B) one is oxidising and the other is reducing (C) one of the steps in endothermic in both the cases (D) all the steps are exothermic in both the reactions 19.

Identify the set of reagents/reaction conditions 'X' and 'Y' in the following set of transformations -[IIT-02] Y X CH 3–CH 2 –CH 2 Br  Product  CH3–CH–CH3

Br (A) X = dilute aqueous NaOH, 20°C, Y= HBr/acetic acid, 20°C (B) X = concentrated alcoholic NaOH, 80°C; Y = HBr/acetic acid, 20° (C) X = dilute aqueous NaOH 20°, Y = Br 2 /CHCl 3 , 0°C (D) X = concentrated alcoholic NaOH, 80°C; Y = Br2 /CHCl 3 , 0°C 20.

F

NO2

(CH3)2NH DMF

(A)

(i) NaNO2 + HCl 0°–5°C (B) (ii) H/Catalytic Reduction 2

[IIT-03]

H3C

(A) O2N

NH2

(B)

N

NH2

N

NO2

H3C

H3C N

H3C

NO2

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(C) H2C

(D) H3C

NH2

CH3 H 21.

CH3 NO2 on hydrolysis in presence of acetone :

MeO H

Cl

CH3

CH3 H

H H CH3

CH3

(K) MeO

(L) MeO

NO2 H

[IIT -05]

OH CH3 CH3

OH CH3

CH3 H

NO2

CH3 NO2

(M) MeO

H CH3 OH (A) K & L

E ALLEN Materials

(B) only L

(C) M only

(D) K & M

41 Provided By - Material Point

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JEE-Chemistry 22.

The reagent (s) for the following conversion :

Br

?

[IIT - 07]

C H is /are -

HC

Br

23.

(A) alcoholic KOH

(B) Alcoholic KOH followed by NaNH 2

(C) aquesous KOH followed by NaNH 2

(D) Zn/CH 3 OH

In the following groups : (I) –OAc ;

[IIT -97]

(II) –OMe ;

(III) –OSO2Me ; (IV) OSO2CF 3

the order of leaving group ability is (A) I > II > III > IV

(B) IV > III > I > II

Aq. KOH

(C) III > II > I > IV

(D) II > III > IV > I

24.

CH3CH2CHCl2

?

[IIT 1991]

25.

Draw the stereochemical structure of the products in the following reaction.

[IIT 1994]

C2H5 

Br

OH / DMSO H   S N2

CH3 Give reasons : H3C

[IIT 2005]

Br CH3

  acidic solution ; (ii) Br— C 2 H 5 OH (aq.)

(a) (i)

CH3 F

C 2 H 5 OH (aq.)   neutral

F NaOH (aq )   F– (liberated) ;

(b) (i) O N 2

CH3

NaOH (aq )   F – is not liberated

(ii) H C 3

CH2NO2

CH3 27.

An alkyl halide ,(A) of formula C 6H 11Cl on treatment with potassium tertiary butoxide gives two isomeric alkenes (B) and (C) C 6H 10 .Both alkene on hydrogenation give methycyclopentane. Predict the structure of (A), (B) and (C).

28.

Which would be the major product in each of the following reactions ?

F

CH3 C 2 H 5 OH   

(a) H3C

CH3

(c)

O

NaOCH 3   

(b)

NO2

base  

Br

42 ALLEN Materials

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26.

E Available on Learnaf.com

JEE-Chemistry 29.

The following compound on hydrolysis in aqueous acetone will give:

CH3 H

CH3

MeO

NO2 H

CH3

Cl

CH3 H (K)

NO2 OH CH3

CH3 H

(M)

\\node6\E_NODE6 (E)\Data\2014\Kota\JEE-Advanced\SMP\Che\Unit-11\Eng\1. Alkyl halide & Aryl halide\Exe.p65

31.

CH3

MeO

NO2 OH H

CH3

CH3 H

CH3

MeO

NO2 H

30.

CH3

MeO H

(L)

[IIT 2005]

It mainly gives (A) K and L Match the following: Column I

CH3 OH

(B) Only K

(C)L and M

(D) Only M [IIT 2006] Column II (P) E1 reaction

(A) CH3–CHBr–CD3 on treatment with alc. KOH gives CH2=CH-CD3 as a major product. (B) Ph – CHBr - CH3 reacts faster than Ph-CHBr-CD3. (C) Ph-CD2-CH2Br on treatment with C2H5OD/C2H5O– gives Ph-CD=CH2 as the major product. (D) PhCH2CH2Br and PhCD2CH2Br react with same rate. The major product of the following reaction is

H3C

(Q) (R)

E2 reaction E1cb reaction

(S)

First order reaction [IIT 2008]

Br F PhSNa   dim ethyl formamide

NO2

SPh

H3C

H3C

SPh

F (A)

F (B)

NO2

E ALLEN Materials

H3 C

H3 C

Br

SPh SPh

SPh (C)

NO2

(D)

NO2

NO2

43 Provided By - Material Point

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JEE-Chemistry 32.

(A)

Br

OCH3 and H2

Br and CH3OH

(C) 33. 34.

HBr OCH3    the products are

In the reaction

[IIT 2010]

(B)

Br and CH3Br

(D)

OH and CH3Br

The total number of alkenes possible by dehydrobromination of 3-bromo-3-cyclopentylhexane using alcoholic KOH is [IIT-2011] KI in acetone, undergoes S N2 reaction with each of P, Q, R and S. The rates of the reaction vary as [IIT 2013]

O Cl Cl

H3C–Cl P

Q

R

S

(A) P > Q > R > S (B) S > P > R > Q (C) P > R > Q > S (D) R > P > S > Q Match the chemical conversions in List-I with the appropritate reagents in List-II and select the correct answer using the code given below this lists [IIT 2013] Li st- I Li st-II (P)

 Cl 

(Q)

 ONa 

OEt

(1)

(i) Hg(OAc) 2 (ii) NaBH 4

(2)

NaOEt

(3)

Et-Br

(4)

(i) BH 3 (ii) H 2O 2 /NaOH

OH

 

(R)

 

(S)

OH Codes : P

Q

R

S

(A)

2

3

1

4

(B)

3

2

1

4

(C)

2

3

4

1

(D)

3

2

4

1

44 ALLEN Materials

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35.

Cl

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JEE-Chemistry ANSWER

P RE VIOU S Y EARS QU E ST ION S

KEY

E XE R CISE - 5

1. (D)

2. (B)

3. (A)

4.(A)

5. (B)

6. (D)

7.(A)

8. (B)

9. (A)

10. (C)

11. (A)

12. (A)

13. (D)

14. (D)

15. (C)

16. (D)

17. (D)

18. (C)

19. (B)

20. (B)

21. (A)

22. (B)

23. (B)

24. CH 3 —CH 2 —CHO

C2H5 25. H

OH CH3

CH3 —C— OC2H5

26. (a) (i) Products are

+ HBr (aq.) ; Hence acidic.

CH3 (ii) No reaction takes place, as aryl halide is inert to nucleophilic subsititution. (b) (i) —NO2 group facilitates the nucleophilic attack because it stabilised the anion formed when attack of OH takes place. (ii) Does not show reaction.

Cl

CH2

CH3

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27. (B)

CH3 (A)

(B)

(C)

OCH3 CH3 28. (a)

(b)

H2C—C=CH—CH3

(c)

O

NO2 29.

A,C

30.

D

34.

B

35.

A

E ALLEN Materials

31.

C

32.

D

33.

A

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