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JEE Advanced

Explore popular questions from Haloalkanes and Haloarenes for JEE Advanced. This collection covers Haloalkanes and Haloarenes previous year JEE Advanced questions hand picked by experienced teachers.

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Haloalkanes and Haloarenes

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Q 1. Chlorobenzene can be prepared by reacting aniline with:

A

hydrochloric acid

B

cuprous chloride

C

chlorine in presence of anhydrous aluminium chloride

nitrous acid followed by heating with cuprous chloride

Explanation

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Q 2. The reaction of toluene with chlorine in presence of ferric chloride gives predominantly:

A

benzoyl chloride

B

{tex} m {/tex} -chlorotoluene

C

benzyl chloride

{tex} o - {/tex} and {tex} p {/tex} -chlorotoluene

Explanation

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Q 3. The number of structural and configurational isomers of a bromo compound, {tex} \mathrm { C } _ { 5 } \mathrm { H } _ { 9 } \mathrm { Br } {/tex}, formed by the addition of {tex} \mathrm {HBr} {/tex} to {tex}2{/tex}-pentyne respectively are

A

1 and 2

2 and 4

C

4 and 2

D

2 and 1

Explanation

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Q 4. {tex} 1 - {/tex} Chlorobutane on reaction with alcoholic potash gives

{tex} 1 - {/tex}butene

B

{tex} 1 - {/tex}butanol

C

{tex} 2 - {/tex}butene

D

{tex} 2 - {/tex} butanol

Explanation

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Q 5. The chief reaction product of reaction between {tex} n {/tex} -butane and bromine at {tex} 130 ^ { \circ } \mathrm { C } {/tex} is:

A

C

D

Explanation

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Q 6. What would be the product formed when {tex} 1 - {/tex} bromo- {tex} 3 - {/tex} chlorocyclobutane reacts with two equivalents of metallic sodium in ether?

A

B

C

Explanation

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Q 7. The reagent(s) for the following conversion,

is/are

A

alcoholic {tex} \mathrm {KOH} {/tex}

alcoholic {tex} \mathrm {KOH} {/tex} followed by {tex} \mathrm {NaNH_2} {/tex}

C

aqueous {tex} \mathrm {KOH} {/tex} followed by {tex} \mathrm {NaNH_2} {/tex}

D

{tex} \mathrm { Zn } / \mathrm { CH } _ { 3 } \mathrm { OH } {/tex}

Explanation

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Q 8. The major product of the following reaction is -

B

C

D

Explanation


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Q 9.

Benzyl chloride ( ) can be prepared from toluene by chlorination with:

A

B

D

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Q 10.

The decreasing leaving group order (fugacity order) of the following compounds is:

i. ii. iii. iv.

A

(i)>(ii)>(iii)>(iv)

(iv)>(iii)>(ii)>(i)

C

(iii)>(i)>(ii)>(iv)

D

(iv)>(ii)>(i)>(iii)

Explanation

Weaker the base, stronger is the leaving group

Fugacity:

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Q 11.

Which is least reactive towards nucleophilic substitution ( )?

A

B

D

Explanation

Aryl halides are least reactive due to resonance

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Q 12.

Which of the following will give mechanism?

A

C

D

Explanation

EWG in benzyl halides favours , but EDG favours

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Q 13.

In the given sequence of reactions, predict (X)

B

C

D

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Q 14.

The decreasing basic order of the following is :

i. ii.

iii. iv.

A

(i)>(ii)>(iii)>(iv)

B

(iv)>(iii)>(ii)>(i)

(ii)>(iv)>(iii)>(i)

D

(iv)>(ii)>(i)>(iii)

Explanation

Stronger the acid, weaker the

  • Sulphonic acids are stronger than carboxylic acids

  • Aromatic sulphonic acids are stronger than aliphatic sulphonic acids

  • More the number of EWG, stronger is the acid

  • Acidic:

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    Q 15.

    The decreasing leaving group order of the following is:

    A

    (i)>(ii)>(iii)>(iv)

    (iv)>(iii)>(ii)>(i)

    C

    (ii)>(i)>(iii)>(iv)

    D

    (ii)>(i)>(iv)>(iii)

    Explanation

    Weaker the base or stronger the acid, stronger is the leaving group

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    Q 16.

    The decreasing nucleophilic order of the following compounds is:

    i. ii. iii. iv.

    A

    (i)>(ii)>(iii)>(iv)

    (iv)>(iii)>(ii)>(i)

    C

    (ii)>(i)>(iii)>(iv)

    D

    (ii)>(i)>(iv)>(iii)

    Explanation

    Since nucleophilic centre is different and they belong to the same group, so basic character and nucleophilicity are reversed

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    Q 17.

    Which of the following has the highest dipole moment?

    A

    B

    C

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    Q 18.

    Benzonitrile on reaction with , followed by hydrolysis, gives

    B

    C

    D

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    Q 19.

    Isopropyl alcohol is heated with a suspension of bleaching powder ( ) with water. The products are:

    A

    Ethane and propane

    B

    Ethyne and ethene

    Trichloromethane and sodium acetate

    D

    Carbon tetrachloride

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    Q 20.

    The product formed by the reaction between 2,2,2-trichloroethanal and chlorobenzene in is:

    A

    Chloretone

    DDT

    C

    Chlorobenzaldichloride

    D

    Benzene sulphonic acid

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    Q 21.

    Propyl lithium reacts with ethene to give a compound (A), which on reaction with methanal followed by acidic hydrolysis gives compound (B). The compound (B) is:

    A

    Heptan-1-ol

    B

    Heptan-2-ol

    Hexan-1-ol

    D

    Hexan-2-ol

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    Q 22.

    Ethylmercaptan is prepared by the reaction of the following, followed by hydrolysis

    A

    C

    D

    Explanation

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    Q 23.

    The reaction of -butyl bromide with sodium methoxide mainly produces:

    A

    Isobutane

    Isobutylene

    C

    -Butyl methyl ether

    D

    Sodium -butoxide

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    Q 24.

    An ethereal solution of 4-nitrochlorobenzene is treated with metallic sodium. The product formed is:

    A

    Aminobenzene

    4,4-Dinitrodiphenyl

    C

    -Chloroaniline

    D

    Benzene diazonium chloride

    Explanation

    Strongly EWG ( group facilitates the reaction

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    Q 25.

    Which is the most effective ion in an displacement on methyl bromide?

    B

    C

    D

    Explanation

    More the nucleophilic character, more is the reaction. Basicity and nucleophilicity are same when the nucleophilic centres are same

    Acidic order:HN > C COOH > OH > O> OH

    Basic and nucleophilic order:

    Therefore, is the most effective nucleophile among the given nucleophiles