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Predict the order of reactivity of the following four isomers towards SN2\text{S}_\text{N}2 reaction. (I) CH3CH2CH2CH2Cl\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{Cl} (II) CH3CH2CH(Cl)CH3\text{CH}_3\text{CH}_2\text{CH}(\text{Cl})\text{CH}_3 (III) (CH3)2CHCH2Cl(\text{CH}_3)_2\text{CHCH}_2\text{Cl} (IV) (CH3)3CCl(\text{CH}_3)_3\text{CCl}

A

(IV) > (III) > (II) > (I)

B

(I) > (II) > (III) > (IV)

C

(I) > (III) > (II) > (IV)

D

(IV) > (II) > (III) > (I)

Step-by-Step Solution

The reactivity of alkyl halides towards SN2\text{S}_\text{N}2 reactions is primarily governed by steric hindrance around the electrophilic carbon atom. The lesser the steric hindrance, the higher the reactivity. Thus, the general order of reactivity is primary (11^{\circ}) > secondary (22^{\circ}) > tertiary (33^{\circ}) .

Analysing the given isomers: (I) CH3CH2CH2CH2Cl\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{Cl} (1-chlorobutane) is a straight-chain primary (11^{\circ}) alkyl halide, which has the least steric hindrance. (III) (CH3)2CHCH2Cl(\text{CH}_3)_2\text{CHCH}_2\text{Cl} (1-chloro-2-methylpropane) is also a primary (11^{\circ}) alkyl halide, but it has a methyl branch at the β\beta-carbon, making it more sterically hindered than isomer (I). (II) CH3CH2CH(Cl)CH3\text{CH}_3\text{CH}_2\text{CH}(\text{Cl})\text{CH}_3 (2-chlorobutane) is a secondary (22^{\circ}) alkyl halide, which is more hindered than the primary halides. (IV) (CH3)3CCl(\text{CH}_3)_3\text{CCl} (2-chloro-2-methylpropane) is a tertiary (33^{\circ}) alkyl halide, which is highly sterically hindered and least reactive towards SN2\text{S}_\text{N}2 substitution.

Therefore, the correct decreasing order of reactivity towards SN2\text{S}_\text{N}2 reaction is (I) > (III) > (II) > (IV) .

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