Reaction of iso-propylbenzene with O2 followed by the treatment with H3O+ forms phenol and a by-product P. Reaction of P with 3 equivalents of Cl2 gives compound Q. Treatment of Q with Ca(OH)2 produces compound R and calcium salt S. The correct statement(s) regarding P, Q, R and S is(are)
(A)Reaction of P with R in the presence of KOH followed by acidification gives (see structure)✓ Correct
(B)Reaction of R with O2 in the presence of light gives phosgene gas✓ Correct
(C)Q reacts with aqueous NaOH to produce Cl3CCH2OH and Cl3CCOONa
(D)S on heating gives P✓ Correct
Answer: (A), (B), (D)
Solution
Cumene (iso-propylbenzene) undergoes cumene hydroperoxide process to give phenol and acetone (P). Acetone reacts with 3 Cl2 to give chloroform (CHCl3, R) and calcium acetate (S) via haloform reaction with Ca(OH)2. (A) Acetone + chloroform with KOH gives chloretone. (B) Chloroform with O2/light gives phosgene (COCl2). (C) is incorrect: Q (CCl3COCH3) does not undergo Cannizzaro reaction. (D) Calcium acetate on heating gives acetone.
JEE Advanced · 2024 · 26 May 2024 · Paper 1 · One or more correct options