The major product obtained in the following reaction is :
(1-phenyl-2-aminopropan-1-ol treated with \(\mathrm{(CH_3CO)_2O}\)/pyridine (1 eqv.), room temp.)
(1-phenyl-2-aminopropan-1-ol treated with \(\mathrm{(CH_3CO)_2O}\)/pyridine (1 eqv.), room temp.)
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The Correct Option is D
Solution and Explanation
With one equivalent of \(\mathrm{(CH_3CO)_2O}\) and pyridine at room temperature, acylation is chemoselective: the amine nitrogen (more nucleophilic than the alcohol oxygen) is acetylated, giving the N-acetyl amide \(\mathrm{PhCH(OH)CH(CH_3)NHCOCH_3}\) while the OH remains free.
This matches option (4) (OH retained, \(\mathrm{NHCOCH_3}\) present). Option (3) is the O-acetylated ester, (2) has an acylated aromatic ring (Friedel-Crafts type, not possible here) and (1) is a dehydrated enamide.
Answer: (4) the N-acetylated product, PhCH(OH)CH(CH3)NHCOCH3
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