Two isomeric compounds
`Cl-CH_2-CH_2-CH_2Cl and CH_3-CH_2-CHCl_2` can be distinguished by the use of

Options

A. `HOH//OH^-`
B. Tollens reagent
C. Both `HOH//OH^(-) ` and Tollens reagent
D. `HOH//OH^-` , Tollens reagent and ceric ammonium nitrate

Answer

To distinguish between the two isomeric compounds \( \text{Cl-CH}_2\text{-CH}_2\text{-CH}_2\text{Cl} \) (1,3-dichloropropane) and \( \text{CH}_3\text{-CH}_2\text{-CHCl}_2 \) (2,2-dichloropropane), we can follow these steps:

### Step 1: Hydrolysis of the Compounds
1. **Hydrolysis of \( \text{Cl-CH}_2\text{-CH}_2\text{-CH}_2\text{Cl} \)**:
- When this compound undergoes hydrolysis, both chlorine atoms are replaced by hydroxyl (OH) groups.
- The product will be \( \text{HO-CH}_2\text{-CH}_2\text{-CH}_2\text{OH} \), which is a diol (specifically, 1,3-propanediol).

2. **Hydrolysis of \( \text{CH}_3\text{-CH}_2\text{-CHCl}_2 \)**:
- In this case, hydrolysis leads to the formation of an aldehyde.
- The product will be \( \text{CH}_3\text{-CH}_2\text{CHO} \) (propanal) after the elimination of one molecule of HCl.

### Step 2: Conducting Tests
3. **Tollens' Test**:
- The aldehyde \( \text{CH}_3\text{-CH}_2\text{CHO} \) can be tested using Tollens' reagent (ammonical silver nitrate).
- A positive result (formation of a silver mirror) indicates the presence of an aldehyde.

4. **Ceric Ammonium Nitrate (CAN) Test**:
- The diol \( \text{HO-CH}_2\text{-CH}_2\text{-CH}_2\text{OH} \) can be tested with ceric ammonium nitrate.
- A positive result (formation of a red complex) indicates the presence of a diol.

### Conclusion
- By performing hydrolysis and subsequent tests, we can distinguish between the two isomers:
- The compound that gives a positive Tollens' test is \( \text{CH}_3\text{-CH}_2\text{-CHCl}_2 \) (2,2-dichloropropane).
- The compound that gives a positive CAN test is \( \text{Cl-CH}_2\text{-CH}_2\text{-CH}_2\text{Cl} \) (1,3-dichloropropane).

### Final Answer
The two isomeric compounds can be distinguished by the use of hydrolysis followed by the Tollens' test and the CAN test.

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