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JEE Main 20236 AprilMorning Shift
Exam
JEE Main
Year
2023
Date
6 April
Shift
Morning Shift
Subject
Chemistry
Chapter
Haloalkanes and Haloarenes

JEE Main 2023 · 6 April · Morning Shift · Chemistry · Haloalkanes and Haloarenes

For the reaction RCH _ 2 Br + I ^ - Acetone ⟶ RCH _ 2 I _ major +...

For the reaction

RCH2Br+I−⟶AcetoneRCH2Imajor+Br−{RCH}_{2}Br + {I}^{-}\overset{\text{Acetone}}{⟶}\mathop{{RCH}_{2}I}_{\text{major}} + {Br}^{-}

The correct statement is

Options

  1. A

    Br–{Br}^{–} can act as competing nucleophile.

  2. B

    The reaction can occur in acetic acid also.

  3. C

    The transition state formed in the above reaction is less polar than the localised anion.

  4. D

    The solvent used in the reaction solvates the ions formed in rate determining step

Correct answer

C.

The transition state formed in the above reaction is less polar than the localised anion.

Step-by-step solution

R−CH2−Br+I−⟶AcetoneR−CH2−I+Br−R - {CH}_{2} - Br + {I}^{-}\overset{\text{Acetone}}{⟶}R - {CH}_{2} - I + {Br}^{-}

As mentioned the reaction follows SN2{S}_{N}2 reaction mechanism. The Finkelstein reaction classically involves the conversion of Alkyl bromides into Alkyl iodides by the treatment with a solution of Sodium iodide in Acetone. NaBrNaBr is not readily soluble in acetone and hence reaction shifts in forward reaction. For SN2{S}_{N}2 reactions, transition state formed is less polar than the localised anion.

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