Reaction of benzyl benzoate with an excess of methyl magnesium bromide generates a mixture of .

Options

A. benzyl alcohol and benzoic acid
B. benzyl methyl ether and 2 - phenylpropan -2- ol
C. benzyl alcohol and 2 - phenylprone - 2- ol
D. ethyl benzene and benzoic acid

Answer

To solve the problem of the reaction of benzyl benzoate with an excess of methyl magnesium bromide (a Grignard reagent), we will follow these steps:

### Step 1: Understand the Reactants
Benzyl benzoate is an ester with the structure:
\[ \text{C}_6\text{H}_5\text{COOCH}_2\text{C}_6\text{H}_5 \]
Methyl magnesium bromide (CH3MgBr) is a Grignard reagent that acts as a nucleophile.

### Step 2: Nucleophilic Attack
In the presence of an excess of methyl magnesium bromide, the nucleophilic methyl group (CH3-) will attack the electrophilic carbon of the carbonyl group in benzyl benzoate. This leads to the formation of a tetrahedral intermediate.

### Step 3: Formation of Acetophenone
The tetrahedral intermediate will collapse, leading to the formation of acetophenone (C6H5COCH3) as one of the products. This occurs because the -O- group leaves as a result of the nucleophilic attack.

### Step 4: Protonation
The negatively charged oxygen from the tetrahedral intermediate will abstract a proton (H+) from the solvent or another source, resulting in the formation of benzyl alcohol (C6H5CH2OH).

### Step 5: Further Reaction
Since we have an excess of methyl magnesium bromide, the acetophenone formed can undergo a second nucleophilic attack by another methyl group from the Grignard reagent. This will lead to the formation of a tertiary alcohol.

### Step 6: Final Product
The final product from the reaction of acetophenone with methyl magnesium bromide will be 2-phenyl-2-propanol (C6H5C(OH)(CH3)CH3), which is a tertiary alcohol.

### Summary of Products
The reaction of benzyl benzoate with excess methyl magnesium bromide generates a mixture of:
1. Benzyl alcohol (C6H5CH2OH)
2. Acetophenone (C6H5COCH3)
3. 2-Phenyl-2-propanol (C6H5C(OH)(CH3)CH3)