Which of the following products is formed when benzaldehyde is treated with `CH_(3)MgBr` and the addition product so obtained is subjected to acid hydrolysis?

Options

A. Secondary alcohol
B. A primary alcohol
C. Phenol
D. Tert-Butyl alcohol

Answer

To solve the question regarding the reaction of benzaldehyde with methylmagnesium bromide (CH₃MgBr) followed by acid hydrolysis, we can follow these steps:

### Step 1: Identify the Reactants
We start with benzaldehyde (C₆H₅CHO) and methylmagnesium bromide (CH₃MgBr). Benzaldehyde is an aromatic aldehyde, and methylmagnesium bromide is a Grignard reagent.

### Step 2: Grignard Reaction
When benzaldehyde reacts with CH₃MgBr, the Grignard reagent acts as a nucleophile. The carbon atom in the carbonyl group (C=O) of benzaldehyde is electrophilic and will react with the nucleophilic carbon from the Grignard reagent.

The reaction can be represented as follows:
\[ \text{C}_6\text{H}_5\text{CHO} + \text{CH}_3\text{MgBr} \rightarrow \text{C}_6\text{H}_5\text{CH(OH)CH}_3\text{MgBr} \]

This results in the formation of an addition product, which is a magnesium alkoxide (C₆H₅CH(OH)CH₃MgBr).

### Step 3: Acid Hydrolysis
The next step is to subject the addition product to acid hydrolysis. This involves adding an acid (commonly HCl or H₂SO₄) to the reaction mixture to protonate the alkoxide and convert it into an alcohol.

The hydrolysis reaction can be represented as:
\[ \text{C}_6\text{H}_5\text{CH(OH)CH}_3\text{MgBr} + \text{H}_2\text{O} \rightarrow \text{C}_6\text{H}_5\text{CH(OH)CH}_3 + \text{MgBrOH} \]

### Step 4: Identify the Final Product
After hydrolysis, the final product is a secondary alcohol, specifically 1-phenyl-2-propanol (C₆H₅CH(OH)CH₃).

### Final Answer
The product formed when benzaldehyde is treated with CH₃MgBr and the addition product is subjected to acid hydrolysis is:
**1-phenyl-2-propanol (C₆H₅CH(OH)CH₃)**, which is a secondary alcohol.