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

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

A. 

B. 

C. 

D. 

  1. A-Br(b);B-I(a);C-Br(a);D-Br(a)
  2. A-Br(b);B-I(b);C-Br(b);D-Br(b)
  3. A-Br(a);B-I(a);C-Br(b);D-Br(a)
  4. A-Br(a);B-I(a);C-Br(a);D-Br(a)

Solution

The leaving group which results in the formation of more stable carbocation will be more reactive towards SN1 reaction.

In the above molecule, by leaving of Br(a) benzyl carbocation is formed. Benzyl carbocation is more stable than aliphatic carbocation.

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

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

Br(a) is more reactive than Br(b) in the above molecule, because tertiary carbocation is more stable than primary carbocation.

Hence, the correct answer is option (3).

 

Asked in: JEE Main 2023 (08 Apr Shift 1)

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