Question

A molecule (P) on treatment with acid undergoes rearrangement and gives (Q). (Q) on ozonolysis followed by reflux under alkaline condition gives (R). The structure of (R) is given below. The structure of (P) is: 
 

• A.
• B.
• C.
• D. Both Option 2 and 3 are correct.

Hint:

In ozonolysis reactions, identify the possible cleavage sites and backtrack to the most probable structure that would result in the given products under the specified conditions.

Answer 1

The Correct Option is A

The first reaction on 'P' is treatment with acid which causes a rearrangement giving 'Q'. Then 'Q' undergoes ozonolysis followed by reflux with alkali to produce 'R'. Ozonolysis will cleave the double bond so let's label the side to add at ketone. Ozonolysis followed by reflux with alkali gives the ketone functionality is. The given product can undergo aldol condensation
If the product given here after reflux with alkali would produce
Given product means Q after ozonolysis with alkaline treatment gave. The first reaction involves acid that give is that the alcohol give alkylene as show n by structure. 

Hence, Both Option 2 and 3 are Correct.