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An organic compound X with the molecular formula C ₈ H ₁₅ NO ₃ yields 6-methylpiperidin-2-one as the major product upon treatment with Br ₂ / NaOH followed by heating. The structure of the starting material X is:

Options

  1. AMethyl 6-carbamoylhexanoate
  2. BMethyl 5-carbamoylhexanoate
  3. CMethyl 4-carbamoylhexanoate
  4. DMethyl 5-aminohexanoate

Correct answer

B. Methyl 5-carbamoylhexanoate

Step-by-step solution

The product, 6-methylpiperidin-2-one, is a 6-membered cyclic amide (lactam) with a methyl group at the 6-position. This lactam is formed by the intramolecular nucleophilic acyl substitution (cyclization) of an intermediate amino ester. Breaking the lactam ring (the bond between the nitrogen and the carbonyl carbon) reveals the intermediate to be methyl 5-aminohexanoate. A 6-membered ring requires the amine to be at C5 of the hexanoate chain. The intermediate is formed via the Hofmann bromamide degradation of X. Thi

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