Pick the major product P in the following reaction (ii) KHCO₃, acetone, 40°C [CbzCl is PhCH₂OCOCl] · ABC26OR0664
Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Reagents, Reaction Mechanisms & Named Reactions – General · Exam: GATE 2000-2022 · Marks: 2 · Difficulty: Medium
Pick the major product P in the following reaction 
(ii) 
$\mathrm{KHCO_3}$, acetone, $40^{\circ}\mathrm{C}$ [CbzCl is $\mathrm{PhCH_2OCOCl}$]
(ii) $\mathrm{KHCO_3}$, acetone, $40^{\circ}\mathrm{C}$ [CbzCl is $\mathrm{PhCH_2OCOCl}$](a)
(b)
(c)
(d)
Answer
Answer: D ✓ checked by 4AB · confidence high
Explanation
CbzCl/NaOH acylates the more nucleophilic amine (N-Cbz serine, hydroxyl untouched); the carboxylate then alkylates the phenacyl bromide (KHCO₃, acetone) to give the phenacyl ester (d).
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