Question

The set(s), in which all the compounds yield achiral products upon treatment with CH\(_3\)MgBr followed by hydrolysis with dilute mineral acid, is(are)

• A. 3,4-epoxyhexane, cyclohexanone, and butanone
• B. ethyl propionate, phenylacetyl chloride, and cyclohexanone
• C. butanone, ethyl propionate, and cyclohexanone
• D. ethyl phenyl ketone, 3,4-epoxyhexane, and phenylacetyl chloride

Hint:

Grignard reagents react with carbonyl compounds to yield alcohols. Symmetric molecules or those with specific stereochemistry yield achiral products after hydrolysis.

Answer 1

The Correct Option is C

Step 1: Analyzing reaction with Grignard reagent (CH\(_3\)MgBr).
- The Grignard reagent reacts with carbonyl compounds (such as ketones and aldehydes), forming an alcohol upon hydrolysis.
- If the compound has symmetry or specific configurations, the product can be achiral.
Step 2: Considering the given options.
- Option (A): 3,4-epoxyhexane, cyclohexanone, and butanone. The epoxy group in 3,4-epoxyhexane reacts with the Grignard reagent to form a symmetric alcohol, which is achiral. Cyclohexanone and butanone will form chiral products after reaction, thus this set does not satisfy the requirement.
- Option (B): ethyl propionate, phenylacetyl chloride, and cyclohexanone. The set contains chiral products. Therefore, not the correct set.
- Option (C): butanone, ethyl propionate, and cyclohexanone are all compounds that will yield achiral products upon reaction with CH\(_3\)MgBr, fulfilling the requirement.
- Option (D): ethyl phenyl ketone, 3,4-epoxyhexane, and phenylacetyl chloride do not all give achiral products.
Final Answer: \[ \boxed{\text{The correct set is (C) butanone, ethyl propionate, and cyclohexanone.}} \]