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JEE Main 202427 JanuaryMorning Shift
Exam
JEE Main
Year
2024
Date
27 January
Shift
Morning Shift
Subject
Chemistry
Chapter
Haloalkanes and Haloarenes

JEE Main 2024 · 27 January · Morning Shift · Chemistry · Haloalkanes and Haloarenes

The correct statement regarding nucleophilic substitution reaction...

The correct statement regarding nucleophilic substitution reaction in a chiral alkyl halide is ;

Options

  1. ARetention occurs in SNl{S}_{N}lreaction and inversion occurs in SN2{S}_{N}2 reaction.
  2. BRacemisation occurs in SNl{S}_{N}lreaction and retention occurs in SN2{S}_{N}2 reaction.
  3. CRacemisation occurs in both SN1{S}_{N}1 and SN2{S}_{N}2 reactions.
  4. DRacemisation occurs in SN1{S}_{N}1 reaction and inversion occurs in SN2{S}_{N}2 reaction.

Correct answer

D. Racemisation occurs in SN1{S}_{N}1 reaction and inversion occurs in SN2{S}_{N}2 reaction.

Step-by-step solution

In the 1st step of SN1{S}_{N}1 mechanism a carbocation is formed which is planar .Therefore the nucleophile can attack the carbocation from both the sides. When a nucleophile attacks the carbocation from the side where initially halogen was there,the product with retention in configuration is produce and when nucleophile attacks the carbocation from backside, the product with inversion in configuration is produce. Hence 5050% of the product will be with retention in configuration and rest 5050% will be with inversion in configuration. This produces a racemic mixture which is optically inactive.

In SN2{S}_{N}2 reaction mechanism requires the attack of nucleophile from the back side of the carbon atom. So the product assumes a stereochemical position opposite to the leaving group originally occupied. This is called inversion of configuration.

SN1{S}_{N}1 – Racemisation

SN2{S}_{N}2 – Inversion

Hence option D is the answer.

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