Propanone on reaction with alkyl magnesium bromide followed by hydrolysis will not produce.

Options

A. Primary alcohol
B. Secondary alcohol
C. Tertiary alcohol
D. Carboxylic acid

Answer

To solve the question, we need to analyze the reaction of propanone with alkyl magnesium bromide (Grignard reagent) followed by hydrolysis.

### Step-by-Step Solution:

1. **Identify the Reactants**:
- The reactant is propanone, which is a ketone with the structure CH3COCH3.

2. **Reaction with Alkyl Magnesium Bromide**:
- When propanone reacts with an alkyl magnesium bromide (R-MgBr), the Grignard reagent acts as a nucleophile and attacks the carbonyl carbon of propanone.
- This results in the formation of a tetrahedral intermediate.

3. **Formation of the Alkoxide**:
- The tetrahedral intermediate will then collapse, leading to the formation of an alkoxide (R2C(OMgBr)R).

4. **Hydrolysis**:
- Upon hydrolysis (usually by adding water or dilute acid), the alkoxide will be converted into an alcohol.
- Since propanone is a ketone, the product will be a tertiary alcohol (R2C(OH)R).

5. **Analyzing the Options**:
- **Option A**: Primary alcohol - Not produced from this reaction.
- **Option B**: Secondary alcohol - Not produced from this reaction.
- **Option C**: Tertiary alcohol - Produced from this reaction.
- **Option D**: Carboxylic acid - Not produced from this reaction.

6. **Conclusion**:
- The reaction of propanone with alkyl magnesium bromide followed by hydrolysis will not produce primary alcohol, secondary alcohol, or carboxylic acid. It will produce tertiary alcohol.

### Final Answer:
Propanone on reaction with alkyl magnesium bromide followed by hydrolysis will not produce:
- **Option A: Primary alcohol**
- **Option B: Secondary alcohol**
- **Option D: Carboxylic acid**