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Chapter 15: Q54. (page 570)

Question: Draw a stepwise mechanism for the following reaction.

Short Answer

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Answer

Mechanism:

Step by step solution

01

N-bromosuccinimide

N-bromosuccinimide is utilized for 鈥渟elective halogenation鈥� at the allylic carbon, i.e., C-H bond, in the presence of light.

02

Mechanism 

Initiation:

In the presence of light, a weak Na-Br bond is NBS is homolytically cleaved, and the bromine radical is formed.

Initiation reaction

Propagation and Termination:

The bromine radical formed in the initiation step and a proton is abstracted from the C-H bond, and an allylic radical is formed. This radical can undergo resonance.

The allylic radical reacts with Br2 to form the C-Br bond.

The propagation step can occur multiple times.

When two radicals combine, a stable product is formed, which terminates the reaction.

Propagation and termination reactions

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