Which of the following alkyl halides on hydrolysis gives a glycol?

Options

A. `CH_(3)CH_(2)CH_(2)Cl`
B. `CH_(3) - underset(Cl)underset(|)(CH)- CH_(2)Cl`
C. `CH_(3)- underset(CH_(3))underset(|)overset(Cl)overset(|)(C ) - CH_(3)`
D. `CH_(3) overset(Cl)overset(|)(C ) HCH_(3)`

Answer

To determine which alkyl halide gives a glycol upon hydrolysis, we need to analyze the options provided. A glycol is defined as an organic compound that contains two hydroxyl (-OH) groups attached to two different carbon atoms.

### Step-by-Step Solution:

1. **Understanding Glycol**:
- A glycol is a compound with two hydroxyl groups (-OH) on different carbon atoms. For example, ethylene glycol (HO-CH2-CH2-OH) has two -OH groups on two different carbons.

**Hint**: Remember that a glycol must have two -OH groups on different carbon atoms.

2. **Analyzing the First Option (CH3CH2CH2Cl)**:
- This compound is a primary alkyl halide. Upon hydrolysis, it will replace the chlorine with a hydroxyl group.
- The reaction will yield CH3CH2CH2OH (propanol), which has only one -OH group.

**Hint**: Check if the product has two -OH groups after hydrolysis.

3. **Analyzing the Second Option (CH3CHClCH3)**:
- This compound is a secondary alkyl halide. Upon hydrolysis, two molecules of water can attack the carbon bonded to chlorine.
- The reaction will yield CH3CHOHCH2OH, which has two -OH groups on different carbons (this is propylene glycol).

**Hint**: Look for the possibility of two -OH groups forming from the hydrolysis.

4. **Analyzing the Third Option**:
- This compound has a structure that will yield only one -OH group upon hydrolysis, similar to the first option.

**Hint**: Again, check if the product has two -OH groups.

5. **Analyzing the Fourth Option**:
- This compound will also yield only one -OH group upon hydrolysis, similar to the first and third options.

**Hint**: Confirm whether the product has two -OH groups.

6. **Conclusion**:
- The only alkyl halide that produces a glycol upon hydrolysis is the second option (CH3CHClCH3), which gives propylene glycol with two -OH groups.

**Final Answer**: The second option is the correct answer, as it gives a glycol upon hydrolysis.