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)
The structure of compound I is
(A)(see structure)✓ Correct
(B)(see structure)
(C)(see structure)
(D)(see structure)
Answer: (A)
Solution
Compound I is the alkene formed by acid-catalyzed dehydration of tertiary alcohol H. Upon ozonolysis, I must give J (phenylacetaldehyde) and K (acetophenone). The structure shown in option (A) is 1,2-diphenylpropene, which upon ozonolysis would give the required products J and K.
JEE Advanced · 2008 · 13 Apr 2008 · Paper 2 · Single correct option
