Of the five isomeric hexanes, the isomers which can give five monochlorinated structural products

Options

A. n-Hexane
B. 2,3-Dimethylbutane
C. 2,2-Dimethybutane
D. 2-Methylpentane

Explanation

To determine which isomer of hexane can give five monochlorinated structural products, we need to analyze the different isomers of hexane based on the number of chemically distinct hydrogen atoms they possess. The isomer with the most distinct hydrogen atoms will yield the maximum number of monochlorinated products.

### Step-by-Step Solution:

1. **Identify the Isomers of Hexane**:
The five isomeric forms of hexane are:
- Hexane (n-hexane)
- 2-methylpentane
- 3-methylpentane
- 2,2-dimethylbutane
- 2,3-dimethylbutane

2. **Analyze n-Hexane**:
- Structure: CH3-CH2-CH2-CH2-CH2-CH3
- All hydrogen atoms are equivalent, leading to only **3 distinct hydrogen atoms**.
- Therefore, it can produce **3 monochlorinated products**.

3. **Analyze 2-Methylpentane**:
- Structure: CH3-CH(CH3)-CH2-CH2-CH3
- Distinct hydrogen atoms:
- 1 from the terminal CH3
- 2 from the CH2 groups
- 2 from the CH group
- Total distinct hydrogen atoms = **5**.
- Thus, it can yield **5 monochlorinated products**.

4. **Analyze 3-Methylpentane**:
- Structure: CH3-CH2-CH(CH3)-CH2-CH3
- Similar to 2-methylpentane, it has **5 distinct hydrogen atoms**.
- Therefore, it can also produce **5 monochlorinated products**.

5. **Analyze 2,2-Dimethylbutane**:
- Structure: CH3-C(CH3)2-CH2-CH3
- Distinct hydrogen atoms:
- 3 from the terminal CH3
- 2 from the CH2
- Total distinct hydrogen atoms = **3**.
- Thus, it can yield **3 monochlorinated products**.

6. **Analyze 2,3-Dimethylbutane**:
- Structure: CH3-CH(CH3)-CH(CH3)-CH3
- Distinct hydrogen atoms:
- 1 from the terminal CH3
- 2 from the CH groups
- 2 from the CH2 groups
- Total distinct hydrogen atoms = **4**.
- Thus, it can yield **4 monochlorinated products**.

### Conclusion:
The isomers of hexane that can give five monochlorinated structural products are **2-methylpentane** and **3-methylpentane**.