Which of the following conditions or reaction sequence will NOT give acetophenone as the major product? (A) (a) (see structure) (b) $\mathrm{Na}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}, \mathrm{H}^{+}$ (B) (see structure) (b) PCC, DCM (C) (see structure) (D) (see structure) $\mathrm{CH}_{3} \mathrm{MgBr}+\mathrm{CdCl}_{2}$

JEE Main · 2022 · 25 Jun 2022 · Shift 2 · Aldehydes Ketones and Carboxylic Acids

Which of the following conditions or reaction sequence will NOT give acetophenone as the major product?
(A) (a) (see structure)
(b)

Na_{2} Cr_{2} O_{7}, H^{+}

(B) (see structure)
(b) PCC, DCM
(C) (see structure)
(D) (see structure)

CH_{3} MgBr + CdCl_{2}

(A)Option A
(B)Option B
(C)Option C✓ Correct
(D)Option D

Answer: (C)

Solution

Acetophenone (

C X_{6} H X_{5} COCH X_{3}

) can be synthesized by various routes. Option (A): Grignard addition to benzoyl compound followed by oxidation gives acetophenone. Option (B): Friedel-Crafts acylation followed by PCC oxidation can give acetophenone. Option (D): Gilman reagent (from

CH X_{3} MgBr + CdCl X_{2}

) reacting with benzoyl chloride gives acetophenone. However, option (C) shows a benzoyl ester, which upon hydrolysis would give benzoic acid, not acetophenone. Therefore, option (C) will NOT give acetophenone as the major product.

JEE Main · 2022 · 25 Jun 2022 · Shift 2 · Single correct option

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JEE Main · 2022 · 25 Jun 2022 · Shift 2 · Aldehydes Ketones and Carboxylic Acids

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