Which of the following isomeric heptanes can yield seven different monochlorinated products upon free radical hlorination ?

Options

A. 3-Methylhexane
B. 2,2-Dimethylpentane
C. 2-Methylhexane
D. 2,3-Dimethylpentane

Explanation

To determine which isomeric heptane can yield seven different monochlorinated products upon free radical chlorination, we need to analyze the structure of each isomer and the number of unique hydrogen atoms that can be replaced by chlorine.

### Step-by-Step Solution:

1. **Understanding Free Radical Chlorination**:
Free radical chlorination involves the substitution of hydrogen atoms with chlorine atoms. The number of different products formed depends on the number of unique hydrogen atoms available for substitution.

2. **Identifying Isomeric Heptanes**:
The isomers of heptane include:
- n-Heptane
- 2-Methylhexane
- 3-Methylhexane
- 2,2-Dimethylpentane
- 2,3-Dimethylpentane
- 2,4-Dimethylpentane
- 3,3-Dimethylpentane
- 3,4-Dimethylpentane

3. **Analyzing 3-Methylhexane**:
- Structure: CH3-CH2-CH(CH3)-CH2-CH2-CH3
- In 3-methylhexane, we can identify the unique hydrogen atoms:
- The terminal CH3 groups (2 equivalent)
- The CH2 groups (4 equivalent)
- The CH group (1 unique)
- This gives us a total of 7 unique hydrogen atoms that can be substituted with chlorine.

4. **Conclusion**:
3-Methylhexane can yield seven different monochlorinated products upon free radical chlorination due to the presence of seven unique hydrogen atoms.

### Final Answer:
The isomeric heptane that can yield seven different monochlorinated products upon free radical chlorination is **3-Methylhexane**.