To determine the compound (X) with the molecular formula \( C_6H_{12}Cl_2 \) that yields a ketone upon hydrolysis, we can follow these steps:
### Step 1: Analyze the Molecular Formula
The molecular formula \( C_6H_{12}Cl_2 \) indicates that the compound contains 6 carbon atoms, 12 hydrogen atoms, and 2 chlorine atoms.
**Hint:** Consider the structure of the compound and how the chlorine atoms might be positioned.
### Step 2: Identify Possible Structures
Given that (X) contains two chlorine atoms, we can consider different structural possibilities, such as:
1. 1,2-dichlorohexane
2. 1,3-dichlorohexane
3. 1,4-dichlorohexane
4. 2,3-dichlorohexane
**Hint:** Think about how the placement of chlorine atoms affects the hydrolysis reaction.
### Step 3: Hydrolysis Reaction
When (X) undergoes hydrolysis, the chlorine atoms will be replaced by hydroxyl (OH) groups. The reaction will also produce hydrochloric acid (HCl) as a byproduct.
**Hint:** Remember that for a compound to yield a ketone, it must have a carbon chain that allows for the formation of a carbonyl (C=O) group.
### Step 4: Evaluate Each Structure
1. **1,2-Dichlorohexane:** Hydrolysis would lead to an alcohol, not a ketone.
2. **1,3-Dichlorohexane:** Hydrolysis would lead to an alcohol, not a ketone.
3. **1,4-Dichlorohexane:** Hydrolysis would lead to an aldehyde, not a ketone.
4. **2,3-Dichlorohexane:** Hydrolysis would replace both Cl with OH, leading to a structure that can form a ketone.
**Hint:** Focus on the structure that allows for the formation of a carbonyl group after losing water.
### Step 5: Confirm the Correct Structure
For **2,3-dichlorohexane**, the hydrolysis would yield:
- The structure after hydrolysis would be \( CH_3CH(OH)CH(OH)CH_2CH_2CH_3 \).
- Upon dehydration (loss of water), this structure can form a ketone \( CH_3C(=O)CH_2CH_2CH_3 \).
**Hint:** Check if the resulting product has the characteristics of a ketone.
### Conclusion
The compound (X) with the molecular formula \( C_6H_{12}Cl_2 \) that gives a ketone upon hydrolysis is **2,3-dichlorohexane**.
**Final Answer:** Option 4 (2,3-dichlorohexane) is the correct answer.
