Solution
Core Logic
The given reactant is p-hydroxybenzaldehyde, which contains both a phenolic -OH group (acidic) and an aldehyde group (electrophilic).
When one equivalent of Grignard reagent (PhMgBr) is added, it behaves primarily as a strong base due to the presence of an acidic proton. Acid-base reactions are extremely fast compared to nucleophilic additions.
The acidic phenolic -OH reacts with PhMgBr:
PhMgBr + HO-C₆H₄-CHO arrow Ph-H (Benzene) + BrMg-O-C₆H₄-CHOUpon workup with aq. NH₄Cl, the phenoxide ion simply regenerates the starting p-hydroxybenzaldehyde. However, the question asks for the number of hydroxyl groups present in the formed product (Benzene).
The distinct product formed in the reaction is Benzene. Benzene has 0 hydroxyl groups.
Pattern Recognition
Whenever a Grignard reagent encounters a molecule with an acidic hydrogen (alcohol, phenol, amine, alkyne), it will invariably act as a base first. If only 1 equivalent is used, nucleophilic addition to carbonyls will NOT happen.
Chapter Mix
Class 12 Chemistry: Aldehydes, Ketones and Carboxylic Acids Class 12 Chemistry: Alcohols, Phenols and Ethers