JEE MainChemistryAlcohols Phenols and Ethers
The cyclic alcohol 1-phenylcyclopentan-1-ol is synthesized by reacting a di-Grignard reagent, prepared from a dihalide 'X', with an ester 'Y', followed by acidic hydrolysis. Identify the correct pair of starting materials 'X' and 'Y'.
Options
- A'X' = 1,5-dibromopentane ; 'Y' = ethyl benzoate
- B'X' = 1,4-dibromobutane ; 'Y' = phenyl acetate
- C'X' = 1,3-dibromopropane ; 'Y' = ethyl benzoate
- D'X' = 1,4-dibromobutane ; 'Y' = ethyl benzoate
Correct answer
D. 'X' = 1,4-dibromobutane ; 'Y' = ethyl benzoate
Step-by-step solution
The target molecule is 1-phenylcyclopentan-1-ol, which contains a five-membered ring with a phenyl group and a hydroxyl group on the same carbon atom. In the reaction of a di-Grignard reagent with an ester, the ester carbonyl carbon becomes the tertiary carbon bearing the hydroxyl group in the final product. The ester must also provide the substituent attached to this carbon. Since the product has a phenyl group on the hydroxyl-bearing carbon, the ester must be a benzoate ester (e.g., ethyl benzoate, PhCOOEt ). The