Q26 · CSIR NET Chemistry, December 2012
Paper: CSIR NET December 2012 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Named Reactions · Marks: 2 · Difficulty: Medium
The major product formed in the following reaction is: 
1. Li, liq. $\mathrm{NH_3}$, t-BuOH 
1. Li, liq. $\mathrm{NH_3}$, t-BuOH (a)
(b)
(c)
(d)
Answer
Answer: B ✓ checked by 4AB · confidence high
Explanation
Birch reduction of 2,6-lutidine gives the 1,4-dihydropyridine (bis-enamine); acid hydrolysis unmasks heptane-2,6-dione, which undergoes intramolecular aldol condensation with KOH to 3-methylcyclohexenone (b).
Study loop for Reagents, Reaction Mechanisms & Named Reactions