Which of the following isomeric heptanes can yield seven differentt monochlorinated products upon free radical chlorination?

Options

A. 2,2-Dimethylpentane
B. 2-methylhexane
C. 3-Methylhexane
D. 2,4-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 available for substitution.

### Step-by-Step Solution:

1. **Identify the Isomers of Heptane**:
Heptane (C7H16) has several structural isomers. The common isomers include:
- n-Heptane
- 2-Methylhexane
- 3-Methylhexane
- 2,2-Dimethylpentane
- 2,3-Dimethylpentane
- 2,4-Dimethylpentane
- 3,3-Dimethylpentane
- 3,2-Dimethylpentane

2. **Analyze Each Isomer for Chlorination**:
- **n-Heptane**: Has 7 equivalent hydrogens on the terminal carbons, yielding only 1 product.
- **2-Methylhexane**: Has 6 unique hydrogens, yielding 6 different products.
- **3-Methylhexane**: Similar to 2-methylhexane, it can yield 6 different products.
- **2,2-Dimethylpentane**: Has 4 equivalent hydrogens on the central carbon, yielding only 4 products.
- **2,3-Dimethylpentane**: Has 6 unique hydrogens, yielding 6 different products.
- **2,4-Dimethylpentane**: This isomer has 7 unique hydrogens, allowing for the formation of 7 different monochlorinated products.
- **3,3-Dimethylpentane**: Similar to 2,2-dimethylpentane, it yields only 4 products.

3. **Conclusion**:
The isomer that can yield seven different monochlorinated products upon free radical chlorination is **2,4-Dimethylpentane**.