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, `Cl-CH2-CH2-CH2Cl` (1,3-dichloropropane) and `CH3-CH2-CHCl2` (1,1-dichloropropane), we can follow these steps:

### Step 1: Identify the Compounds
- The first compound is 1,3-dichloropropane (`Cl-CH2-CH2-CH2Cl`), which has chlorine atoms on the first and third carbon.
- The second compound is 1,1-dichloropropane (`CH3-CH2-CHCl2`), which has two chlorine atoms on the first carbon.

### Step 2: Perform Hydrolysis
- When both compounds are treated with aqueous hydroxide ions (OH-), hydrolysis occurs.
- For 1,3-dichloropropane, hydrolysis will replace the chlorine atoms with hydroxyl (OH) groups, resulting in a diol: `HO-CH2-CH2-CH2-OH`.
- For 1,1-dichloropropane, hydrolysis will also replace the chlorine atoms, but due to the presence of two chlorines on the same carbon, it will lead to the formation of an aldehyde: `HO-CH2-CHO`.

### Step 3: Distinguish Using Tollen's Reagent
- Tollen's reagent (Ag(NH3)2OH) can be used to test for aldehydes.
- When Tollen's reagent is added to the product from 1,1-dichloropropane, a silver mirror forms due to the oxidation of the aldehyde.
- In contrast, the product from 1,3-dichloropropane will not produce a silver mirror because it does not contain an aldehyde group.

### Step 4: Confirm with Ceric Ammonium Nitrate (CAN)
- Ceric ammonium nitrate can also be used to distinguish between the two compounds.
- The product from 1,1-dichloropropane (which has an aldehyde) will give a positive test with CAN, resulting in a red color.
- The product from 1,3-dichloropropane will not produce a red color since it does not have an aldehyde.

### Conclusion
- The two isomeric compounds can be distinguished by using both Tollen's reagent and ceric ammonium nitrate after hydrolysis. Therefore, the correct answer is option 4: "water OH-, Tollen's reagent, and ceric ammonium nitrate."

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