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NEET CHEMISTRYHaloalkanes and HaloarenesMedium

Question

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) .

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Haloalkanes and Haloarenes. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYHaloalkanes and Haloarenespredictreactivityfollowingisomerstowards

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