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Compound (X) having molecular formula C6...

Compound (X) having molecular formula `C_6H_(12)Cl_2` on hydrolysis gives a ketone. Therefore (X) will be

A

`CH_3-overset(Cl)overset(|)(CH)-CH_2-overset(Cl)overset(|)(CH)-CH_2-CH_3`

B

`CH_3-overset(Cl)overset(|)(CH)-CH_2-CH_2-CH_2-CH_2-Cl`

C

`CH_3-CH_2-CH_2-CH_2-CH_2-CHCl_2`

D

`CH_3-CH_2-CH_2-underset(Cl)underset(|)overset(Cl)overset(|)C-CH_2-CH_3`

Text Solution

AI Generated Solution

The correct Answer is:
To determine the compound (X) with the molecular formula C₆H₁₂Cl₂ that gives a ketone upon hydrolysis, we can follow these steps: ### Step 1: Analyze the Molecular Formula The molecular formula C₆H₁₂Cl₂ indicates that the compound has 6 carbon atoms, 12 hydrogen atoms, and 2 chlorine atoms. The presence of two chlorine atoms suggests that the compound could be a dihaloalkane. **Hint:** Look for the structure that can lead to a ketone after hydrolysis. ### Step 2: Understand Hydrolysis Hydrolysis involves the reaction of the compound with water, where the chlorine atoms are replaced by hydroxyl (OH) groups. This process can lead to the formation of either an alcohol, an aldehyde, or a ketone depending on the structure of the original compound. **Hint:** Consider how the placement of chlorine affects the outcome of hydrolysis. ### Step 3: Consider Possible Structures We need to consider different structural isomers of C₆H₁₂Cl₂. The key is to find a structure where the hydrolysis will yield a ketone. A ketone has the general structure R-CO-R', where R and R' are alkyl groups. **Hint:** Focus on structures where both chlorine atoms are on the same carbon atom, as this can lead to the formation of a ketone. ### Step 4: Evaluate Each Isomer 1. **Isomer 1:** Cl on different carbons - Hydrolysis would yield an alcohol, not a ketone. 2. **Isomer 2:** Cl on different carbons - Hydrolysis would yield an alcohol, not a ketone. 3. **Isomer 3:** Cl on the same carbon - Hydrolysis leads to the formation of an aldehyde. 4. **Isomer 4:** Cl on the same carbon - Hydrolysis leads to the formation of a ketone. **Hint:** Pay attention to the carbon skeleton and the position of the chlorine atoms. ### Step 5: Identify the Correct Structure From the evaluation, Isomer 4 is the only structure that leads to the formation of a ketone upon hydrolysis. The reaction would involve the removal of HCl and the formation of a carbonyl group (C=O) with alkyl groups on both sides. **Hint:** Confirm that the resulting structure after hydrolysis fits the definition of a ketone. ### Conclusion The compound (X) with the molecular formula C₆H₁₂Cl₂ that gives a ketone upon hydrolysis is the fourth isomer. **Final Answer:** Compound (X) is the fourth isomer of C₆H₁₂Cl₂.
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