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Acid-Catalyzed Alpha-Halogentation

24. Enolate Chemistry: Reactions at the Alpha-Carbon / Acid-Catalyzed Alpha-Halogentation / Problem 4

Suggest a synthetic pathway to produce the following compound from the given starting material.

A

Acid-catalyzed alpha-halogentation of 3-methylbutanoate with HBr and water.

B

Synthetic pathway using PBr3 and H2O to convert 3-methylbutanoate to a brominated product.

C

Acid-catalyzed reaction of 3-methylbutanoate with HBr and water to yield a product with CH3SH.

D

Synthetic pathway using PBr3 and H2O to convert 3-methylbutanoate to a product with CH3SH.

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