Q15 · CSIR NET Chemistry, December 2013
Paper: CSIR NET December 2013 · Subject: Organic Chemistry · Chapter: Natural Products · Topic: Natural Products – General · Marks: 2 · Difficulty: Medium
The major product B formed in the following reaction sequence, and overall yield of its formation are (S)-glutamic acid $180\,^{\circ}\mathrm{C}$, 60% A 80% B
(a)
and 48 %
and 48 %(b)
and 70 %
and 70 %(c)
and 48 %
and 48 %(d)
and 70 %
and 70 %Answer
Answer: A ✓ checked by 4AB · confidence high
Explanation
Heating (S)-glutamic acid with the amine gives the (S)-pyroglutamide (A, 60 %); LiAlH₄ reduces both amides to give (S)-2-(anilinomethyl)pyrrolidine (B) with retention. Overall yield 0.60 × 0.80 = 48 %.
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