Q106 · CSIR NET Chemistry, June 2016
Paper: CSIR NET June 2016 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Reagents, Reaction Mechanisms & Named Reactions – General · Marks: 2 · Difficulty: Medium
The major product formed in the following reaction sequence is: 
3. $\mathrm{H_3O^{+}}$
3. $\mathrm{H_3O^{+}}$(a)
(b)
(c)
(d)
Answer
Answer: C ✓ checked by 4AB · confidence high
Explanation
Ethylene glycol/TsOH protects the ketone as the ketal; the Tebbe reagent methylenates the ester to the enol ether; aqueous acid hydrolyses the enol ether to the methyl ketone and removes the ketal (c).
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