A compound (A), `C_(4)H_(8)Cl_(2)` , on hydrolysis gives a product(B) which forms a 2,4-DNP derivation,but does not reduce Tollen's reagent. The compoun (A) has the structure:

Options

A. `CH_(3)CH_(2)CHClCH_(2)Cl`
B. `CH_(3)CH_(2)"CC"l_(2)CH_(3)`
C. `CH_(3)CH_(2)CH_(2)CHCl_(2)`
D. `CH_(3)CHClCHClCh_(3)`

Answer

To determine the structure of compound (A) with the molecular formula C4H8Cl2, we need to analyze the information provided step by step.

### Step 1: Understanding the Hydrolysis Product
The compound (A) upon hydrolysis gives a product (B) that forms a 2,4-DNP derivative but does not reduce Tollen's reagent. This indicates that product (B) is likely a ketone because:
- 2,4-DNP (2,4-dinitrophenylhydrazine) reacts with ketones and aldehydes, forming a colored precipitate.
- The fact that it does not reduce Tollen's reagent suggests that product (B) is not an aldehyde (as aldehydes can reduce Tollen's reagent).

### Step 2: Analyzing the Molecular Formula
Given the molecular formula C4H8Cl2, we can deduce that:
- The presence of two chlorine atoms suggests that they are likely attached to the same carbon to form a more stable compound after hydrolysis.
- The structure must allow for the formation of a ketone after hydrolysis.

### Step 3: Proposed Structure of Compound (A)
To achieve a ketone after hydrolysis, we can consider a structure where both chlorine atoms are attached to the same carbon atom. A suitable structure for (A) could be:

```
CH3
|
CH3-CH-CCl2
|
CH2
```

This structure indicates that the compound (A) is 2,2-dichlorobutane.

### Step 4: Hydrolysis Reaction
When 2,2-dichlorobutane undergoes hydrolysis, it reacts with water in the presence of a base (like KOH) to replace the chlorine atoms with hydroxyl groups (OH). The reaction can be represented as follows:

```
CH3
|
CH3-CH-CCl2 + 2 H2O → CH3-CH-C(OH)2 + 2 HCl
```

After hydrolysis, the compound will have two hydroxyl groups on the same carbon, which can then lose water to form a ketone:

```
CH3
|
CH3-CH-C(OH)2 → CH3-CO-CH2-CH3 + H2O
```

### Step 5: Final Product (B)
The final product (B) is 2-butanone (or methyl ethyl ketone), which has the structure:

```
CH3
|
CH3-C=O
|
CH2
```

This compound will give a positive test with 2,4-DNP and a negative test with Tollen's reagent.

### Conclusion
Thus, the structure of compound (A) is 2,2-dichlorobutane, which can be represented as:

```
CH3
|
CH3-CH-CCl2
|
CH2
```