JEE Main 2022 · 25 Jun · Shift 2 · Chemistry Q77

ChemistrySingle correct+4 / -1Question 77 of 90

Which of the following conditions or reaction sequence will NOT give acetophenone as the major product ?

(a)

\mathrm{C_6H_5CHO+CH_3MgBr}

(b)

\mathrm{Na_2Cr_2O_7,H^+}

(a)

\mathrm{CH_3CHO+C_6H_5MgBr}

(b) PCC, DCM

\mathrm{C_6H_5COOC_2H_5+2CH_3MgBr}

\mathrm{C_6H_5COCl+CH_3MgBr+CdCl_2}

Answer and worked solution

Official answer: C

Check each.

(A) $\mathrm{C_6H_5CH(OH)CH_3}$ , then oxidation: acetophenone.
(B) the same secondary alcohol, then PCC: acetophenone.
(C) An ester with 2 $\mathrm{CH_3MgBr}$ goes past the ketone to the tertiary alcohol $\mathrm{C_6H_5C(OH)(CH_3)_2}$ .
(D) Dimethylcadmium with the acid chloride stops at the ketone: acetophenone.

(C)

Topics:Nucleophilic addition Oxidation and reduction

JEE Main 2022 · 25 Jun · Shift 2, Chemistry question 77