Q11 · CSIR-NET Chemistry, December 2018

Paper: CSIR-NET December 2018 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Reagents, Reaction Mechanisms & Named Reactions – General · Marks: 2 · Difficulty: Hard

Both 1-chloro-1-phenylpropan-2-one and 1-chloro-3-phenylpropan-2-one give same product A when heated in presence of NaOMe. The product A is
(a)Methyl 3-phenylpropanoate
(b)Methyl 2- phenylpropanoate
(c)Methyl 2-methoxy-2-phenylacetate
(d)1-methoxy-3-phenylpropan-2-one
Answer
Answer: A ✓ checked by 4AB · confidence high
Explanation
Favorskii: both α-chloroketones give the same cyclopropanone; methoxide opens it to form the more stable benzylic carbanion, giving methyl 3-phenylpropanoate (a).

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