JEE Advanced · 2006 · 09 Apr 2006 · Hydrocarbons

The major products P and Q are

(A)(see structure) and $CH_{3} CH_{2} CHO$
(B)(see structure) and $CH_{3} COCH_{3}$
(C)(see structure) and $CH_{3} COCH_{3}$
✓ Correct
(D)(see structure) $CH_{3} CH_{2} CHO$

Answer: (C)

Solution

This is the cumene hydroperoxide rearrangement reaction. Cumene (isopropylbenzene) is oxidized to cumene hydroperoxide, which then undergoes acid-catalyzed rearrangement. The O-O bond breaks, and a phenyl group migrates to form phenol and acetone. Product P is phenol (with the isopropyl group, shown in option C) and product Q is acetone (

CH_{3} COCH_{3}

JEE Advanced · 2006 · 09 Apr 2006 · One or more correct options

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