What product is obtained when propanoic acid is treated with bromine in the presence of red phosphorus followed by hydrolysis?
Answer and explanation
Correct answer: A. 2-Bromopropanoic acid
- Step 1: The Hell-Volhard-Zelinsky (HVZ) reaction selectively brominates carboxylic acids containing alpha-hydrogens at the alpha-carbon position.
- Step 2: Propanoic acid () has its alpha-carbon at position 2, yielding 2-bromopropanoic acid upon bromination and water workup.
Answer
2-Bromopropanoic acid.
Why not the others: 3-Bromopropanoic acid brominates the beta-position, which does not occur under HVZ conditions; dibromination requires excess reagent; and propanoyl bromide hydrolyzes back to acid.
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