Q25 · CSIR NET Chemistry, December 2012
Paper: CSIR NET December 2012 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Reagents, Reaction Mechanisms & Named Reactions – General · Marks: 2 · Difficulty: Medium
The major product B formed in the following reaction sequence is 
1. $\mathrm{CH_2N_2}$, $\mathrm{Et_2O}$ 
(B)
1. $\mathrm{CH_2N_2}$, $\mathrm{Et_2O}$ (B)(a)
(b)
(c)
(d)
Answer
Answer: A ✓ checked by 4AB · confidence high
Explanation
CH₂N₂ O-methylates the enolic 1,3-diketone to 3-methoxycyclohexenone; MeMgCl adds 1,2 and aqueous acid hydrolyses the resulting enol ether/eliminates to 3-methylcyclohexenone (a).
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