Question 6
Reaction of iso-propylbenzene with followed by the treatment with forms phenol and a by-product . Reaction of with 3 equivalents of gives compound . Treatment of with produces compound and calcium salt . The correct statement(s) regarding and is(are)
Reaction of with in the presence of light gives phosgene gas
reacts with aqueous to produce and
on heating gives
Reaction of with in the presence of followed by acidification gives

Detailed Solution
- iso-propylbenzene (Cumene) reacts with to form Cumene hydroperoxide, which on hydrolysis with gives Phenol and Acetone ().
So, is .
-
() with 3 equivalents of undergo alpha-halogenation to give 1,1,1-trichloroacetone (), which is .
-
() treated with undergoes the haloform reaction to produce Chloroform (, ) and Calcium acetate (, ).
Analyzing options:
(A) Acetone () reacts with Chloroform () in the presence of to form Chloretone (). Correct.
(B) Chloroform (, ) reacts with in the presence of light to form Carbonyl chloride (), also known as phosgene. Correct.
(C) () with aq. undergoes haloform cleavage to give and , not the disproportionation products of chloral. Incorrect.
(D) Calcium acetate () on dry distillation (heating) produces acetone () and . Correct.
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