Choose the halogen which is most reactive towards SN1 reaction in the given compounds (A, B, C & D) A. ![JEE Main 2023 Chemistry, Haloalkanes and Haloarenes — question figure 1](https://prepforbharat.s3.ap-south-1.amazonaws.com/exam/615f0e999476412f48314daf/Chemistry/images/Haloalkanes_and_Haloarenes/648b5a70417cc3fb48d68403/question_1__q_648b5a70417cc3fb48d68403__cdn-question-pool.getmarks.app__6f06b262-7155-41aa-bb1a-4ab072dca3c0__d5bb2f532a_final_ppt_sync.png) B. ![JEE Main 2023 Chemistry, Haloalkanes and Haloarenes — question figure 2](https://prepforbharat.s3.ap-south-1.amazonaws.com/exam/615f0e999476412f48314daf/Chemistry/images/Haloalkanes_and_Haloarenes/648b5a70417cc3fb48d68403/question_2__q_648b5a70417cc3fb48d68403__cdn-question-pool.getmarks.app__bc464402-0744-4ff9-8362-3e7ce7134916__5720cdb1da_final_ppt_sync.png) C. ![JEE Main 2023 Chemistry, Haloalkanes and Haloarenes — question figure 3](https://prepforbharat.s3.ap-south-1.amazonaws.com/exam/615f0e999476412f48314daf/Chemistry/images/Haloalkanes_and_Haloarenes/648b5a70417cc3fb48d68403/question_3__q_648b5a70417cc3fb48d68403__cdn-question-pool.getmarks.app__5c8d8b32-a2b3-4f7e-9539-485e2c0c12bf__b81abb4f1a_final_ppt_sync.png) D. ![JEE Main 2023 Chemistry, Haloalkanes and Haloarenes — question figure 4](https://prepforbharat.s3.ap-south-1.amazonaws.com/exam/615f0e999476412f48314daf/Chemistry/images/Haloalkanes_and_Haloarenes/648b5a70417cc3fb48d68403/question_4__q_648b5a70417cc3fb48d68403__cdn-question-pool.getmarks.app__06c7a3e2-2c93-4164-9a46-4431a3814ecb__041b74253b_final_ppt_sync.png)

JEE Main 2023 — Chemistry Organic Chemistry

2023mcqmedium

Choose the halogen which is most reactive towards SN1 reaction in the given compounds (A, B, C & D)

A. JEE Main 2023 Chemistry, Haloalkanes and Haloarenes — question figure 1

B. JEE Main 2023 Chemistry, Haloalkanes and Haloarenes — question figure 2

C. JEE Main 2023 Chemistry, Haloalkanes and Haloarenes — question figure 3

D. JEE Main 2023 Chemistry, Haloalkanes and Haloarenes — question figure 4

Official previous-year question

Held on 8 Apr 2023 · Verified 6 Jul 2026.

Options

A
$A-{\mathrm{Br}}_{(b)};B-{I}_{(a)};C-{\mathrm{Br}}_{(a)};D-{\mathrm{Br}}_{(a)}$
B
$A-\mathrm{Br}(b);B-{I}_{(b)};C-\mathrm{Br}(b);D-\mathrm{Br}(b)$
C
$A-{\mathrm{Br}}_{(a)};B-{I}_{(a)};C-{\mathrm{Br}}_{(b)};D-{\mathrm{Br}}_{(a)}$
D
$A-{\mathrm{Br}}_{(a)};B-{I}_{(a)};C-{\mathrm{Br}}_{(a)};D-{\mathrm{Br}}_{(a)}$

Did you get this right?

Solution

The leaving group which results in the formation of more stable carbocation will be more reactive towards S $_{N}$ 1 reaction.

JEE Main 2023 Chemistry, Haloalkanes and Haloarenes — solution figure 1

In the above molecule, by leaving of ${\mathrm{Br}}_{(a)}$ benzyl carbocation is formed. Benzyl carbocation is more stable than aliphatic carbocation.

JEE Main 2023 Chemistry, Haloalkanes and Haloarenes — solution figure 2

By replacing ${I}_{(a)}$ in the above molecule, allyl carbocation is formed. Allyl carbocation is more stable than aliphatic carbocation.

JEE Main 2023 Chemistry, Haloalkanes and Haloarenes — solution figure 3

In the above molecule, it is difficult to replace ${\mathrm{Br}}_{(a)}$ , as carbocation formed at bridge head position is very difficult. Hence, ${\mathrm{Br}}_{(b)}$ is more reactive.

JEE Main 2023 Chemistry, Haloalkanes and Haloarenes — solution figure 4

${\mathrm{Br}}_{(a)}$ is more reactive than ${\mathrm{Br}}_{(b)}$ in the above molecule, because tertiary carbocation is more stable than primary carbocation.

Hence, the correct answer is option (3).

Your note

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Options

$A-{\mathrm{Br}}_{(b)};B-{I}_{(a)};C-{\mathrm{Br}}_{(a)};D-{\mathrm{Br}}_{(a)}$

$A-\mathrm{Br}(b);B-{I}_{(b)};C-\mathrm{Br}(b);D-\mathrm{Br}(b)$

$A-{\mathrm{Br}}_{(a)};B-{I}_{(a)};C-{\mathrm{Br}}_{(b)};D-{\mathrm{Br}}_{(a)}$

$A-{\mathrm{Br}}_{(a)};B-{I}_{(a)};C-{\mathrm{Br}}_{(a)};D-{\mathrm{Br}}_{(a)}$