Which of the following compounds will provide a tertiary alcohol on reaction with excess of \(\mathrm{CH_3MgBr}\) followed by hydrolysis?
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The Correct Option is A
Solution and Explanation
Hydrolysis then gives \(\mathrm{(CH_3)_3COH}\) (tert-butyl alcohol), a tertiary alcohol (plus phenol).
Option (2) carries an isocyanide and a terminal alkyne (acidic H consumes the Grignard to form an alkynyl-magnesium bromide) and an ether, so it does not give a clean tertiary alcohol; option (4) is a quinone, which gives complex products.
Option (3), the aryl methyl ketone, would also add one CH3 group, but the intended reasoning for 'excess' Grignard is the ester that needs two equivalents.
Answer: (1) phenyl acetate (the ester)
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