Which of the compounds with molecular formula `C_(5)H_(10)`yields acetone on ozonolysis ?

Options

A. 2-Methyl-1-butene
B. 2-Methyl-2-butene
C. 3-Methyl-1-butene
D. Cyclopentane

Answer

To determine which compound with the molecular formula C5H10 yields acetone on ozonolysis, we will analyze the ozonolysis products of each compound systematically.

### Step-by-Step Solution:

1. **Identify the Compounds**: The compounds with the molecular formula C5H10 that we need to consider are:
- 2-methyl-1-butene
- 2-methyl-2-butene
- 3-methyl-1-butene
- Cyclopentane

2. **Ozonolysis of 2-methyl-1-butene**:
- Structure: CH2=C(CH3)CH2CH3
- When ozonolysis occurs, the double bond breaks and forms an ozonide intermediate.
- The ozonide then undergoes reductive workup (using Me2S).
- Products formed:
- CH3CH2C(=O)CH3 (butan-2-one)
- CH3CHO (acetaldehyde)
- **Conclusion**: Does not yield acetone.

3. **Ozonolysis of 2-methyl-2-butene**:
- Structure: CH3C(=C(CH3)CH2)CH3
- Ozonolysis leads to the breaking of the double bond and formation of an ozonide.
- Products formed:
- CH3C(=O)CH3 (acetone)
- CH3CHO (acetaldehyde)
- **Conclusion**: Yields acetone.

4. **Ozonolysis of 3-methyl-1-butene**:
- Structure: CH2=C(CH3)CH2CH3
- Similar to 2-methyl-1-butene, ozonolysis results in:
- CH3C(=O)H (acetaldehyde)
- CH3CH2C(=O)H (butanal)
- **Conclusion**: Does not yield acetone.

5. **Ozonolysis of Cyclopentane**:
- Structure: C5H10 (cyclic structure)
- Cyclopentane does not have any double bonds to undergo ozonolysis.
- **Conclusion**: Does not yield acetone.

### Final Answer:
The compound with the molecular formula C5H10 that yields acetone on ozonolysis is **2-methyl-2-butene**.

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