Question

The compound(s) which on reaction with CH₃MgBr followed by treatment with aqueous NH₄Cl would produce 1-methyl-1-phenylethanol as the major product is/are

• A. methyl benzoate
• B. phenyl acetate.
• C. acetaldehyde.
• D. acetophenone.

Answer 1

The Correct Option is A, D

• (A) Methyl benzoate, upon reaction with CH₃MgBr, undergoes nucleophilic addition forming a magnesium alkoxide intermediate. After treatment with aqueous NH₄Cl, the final product formed is 1-methyl-1-phenylethanol.
• (B) Phenyl acetate would not give the desired product because it does not have the correct functionality for forming the required alcohol.
• (C) Acetaldehyde would lead to a different product because it is a simple aldehyde and does not have the ester group required for this transformation.
• (D) Acetophenone, when reacted with CH₃MgBr, would result in the formation of a magnesium alkoxide intermediate which after treatment with aqueous NH₄Cl would form 1-methyl-1-phenylethanol.

Thus, the correct answers are (A) and (D).