Q12 · CSIR-NET Chemistry, June 2016
Paper: CSIR-NET June 2016 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Named Reactions · 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 products in the following reaction is: 
(a)
(b)
(c)
(d)
Answer
Under review — not yet confirmed.
Answer: C
The source book printed no answer; this one was worked out and checked — see the explanation.
Explanation
Two equivalents of s-BuLi deprotonate the NH₂ and then the benzylic methyl (lateral lithiation directed by the amide). The carbanion attacks the thiophene ester, and the resulting ketone condenses with the amine to give the 2-(2-thienyl)-6-azaindole (c).
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