Consider the reaction: H_3C- D | CH - Br | CH -CH_3 + B r 'X' + HBr Identify the structure of the major product 'X':

JEE Main Chemistry question

Consider the reaction:

--- + r → 'X' + HBr

Identify the structure of the major product 'X':

(A)[radical at the deuterium-bearing carbon]
(B)[radical at the carbon bearing bromine, retaining the deuterium label elsewhere]Correct
(C)[radical formed by loss of the deuterium atom]
(D)[radical at the terminal methyl carbon]

Answer: (B)

Solution

Bromine radical abstracts a hydrogen atom preferentially over a deuterium atom (the kinetic isotope effect: the bond is weaker and breaks faster than the stronger bond), and among the available bonds it preferentially abstracts the hydrogen that generates the more stable (more substituted) radical.

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Question ID VK-148161