A tertiary alcohol H upon acid catalysed dehydration gives a product I. Ozonolysis of I leads to compounds J and K. Compound J upon reaction with KOH gives benzyl alcohol and a compound L, whereas K on reaction with KOH gives only M. (see structure of M)
Compound H is formed by the reaction of
(A)(see structure)
(B)(see structure)✓ Correct
(C)(see structure)
(D)(see structure)
Answer: (B)
Solution
Working backwards from the given structure of M and the reaction conditions, compound H must be a tertiary alcohol that upon dehydration gives an alkene I. Ozonolysis of I produces J and K. Since J gives benzyl alcohol and L upon reaction with KOH (Cannizzaro reaction), J must be phenylacetaldehyde. K gives only M upon KOH treatment. The structure of H is formed by the Grignard reaction shown in option (B), where phenylmagnesium bromide reacts with acetophenone to form the tertiary alcohol H.
JEE Advanced · 2008 · 13 Apr 2008 · Paper 2 · Single correct option
