Question

In the following reaction, the major product (H) is

• A. Option a
• B. Option b
• C. Option c
• D. Option d

Hint:

Grignard tips: 

 Always attacks carbonyl first 

Intramolecular cyclization possible 

Workup gives alcohol/ether products 

Answer 1

The Correct Option is D

Concept:
Grignard reagents:
Attack electrophilic carbonyl carbon
Also react with alkyl halides intramolecularly if possible
Step 1: Functional groups
Molecule contains:
Ketone
Alkyl chloride in same chain
Step 2: Reaction pathway
MeMgBr first forms alkoxide via addition to ketone.
Intramolecular nucleophilic substitution occurs forming cyclic ether.
Step 3: After hydrolysis
Protonation gives cyclic ether with allylic side chain.
Conclusion:
Structure corresponding to option (D) forms.