#27 A certain compound a, when treated with...

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Question

#27 A certain compound a, when treated with N-bromosuccinimide and benzoyl peroxide under photochemical conditions in refluxing carbon tetrachloride, gave 3,4,5-tribromo benzyl bromide in excellent yield. Deduce the structure of compound A.

Answer

Step 1 - The structure of 3, 4, 5-tribromobenzyl bromide is as follows:

Step 2 - N-bromosuccinimide is selective brominating agent for allylic or benzylic position. The retro analysis of target molecule 3, 4, 5-tribromobenzyl bromide is as follows:

Step - 3 Bromination of 1,2,3-tribromo-5-methylbezene with N-bromosuccinimide in the presence of benzoyl peroxide under photochemical conditions in refluxing carbon tetrachloride gives desired product 3, 4, 5-tribromobenzyl bromide.