Q10 · CSIR-NET Chemistry, December 2014
Paper: CSIR-NET December 2014 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Reagents, Reaction Mechanisms & Named Reactions – General · Marks: 2 · Difficulty: Medium
Under review — part of this question (a structure or an option) is not clear in the source scan. 4AB is checking it against the original book; the answer shown may change.
The major product formed in the following reaction sequence is: 
(a)
(b)
(c)
(d)
Answer
Under review — not yet confirmed.
Answer: C
The source book printed A; on checking, C is correct — see the explanation.
Explanation
Dissolving-metal (Na/NH₃) conditions Birch-reduce the arene to the 1,4-diene with both alkyl groups on sp² carbons and reduce the internal alkyne to the (E)-alkene (c).
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