The major product of the following chemical reaction is :
Correct Answer :
(CH3)2CH-CH2-CH2-Br
Solution :
The correct answer is (CH3)2CH-CH2-CH2-Br (1-bromo-3-methylbutane).
Reaction Analysis:
The given reaction is the addition of hydrogen bromide (HBr) to an alkene, specifically 3-methylbut-1-ene, in the presence of benzoyl peroxide, .
When HBr reacts with an unsymmetrical alkene in the presence of a peroxide, the addition follows an anti-Markovnikov pathway (also known as the peroxide effect or Kharasch effect), which proceeds via a free-radical mechanism.
Step-by-step Mechanism:
1. Chain Initiation:
The peroxide initiator decomposes homolytically to produce radicals, which then react with HBr to generate a bromine radical (Br•):
2. Chain Propagation:
The bromine radical attacks the double bond of 3-methylbut-1-ene. The addition occurs selectively at the terminal carbon atom to form a more stable secondary carbon radical instead of a less stable primary carbon radical:
This secondary radical then abstracts a hydrogen atom from another HBr molecule to form the final product and regenerate the bromine radical:
Unlike carbocation intermediates, free-radical intermediates do not undergo rearrangement under these standard conditions. Therefore, the major product is the non-rearranged anti-Markovnikov addition product: 1-bromo-3-methylbutane.
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