An organic compound `A(C_(4)H_(6)CI)` on reation withNa/diethyl ether gives a hydrocarbon which on monochlorination gives only one chloro derivative `A` is .

Options

A. t-butyl chloride
B. sec. butyl chloride
C. Iso butyl chloride
D. n-butyl chloride

Answer

To solve the question, we need to identify the organic compound A (C₄H₆Cl) that, when reacted with sodium in diethyl ether, produces a hydrocarbon which gives only one monochlorinated derivative.

### Step-by-Step Solution:

1. **Identify the Structure of Compound A**:
The compound A has the molecular formula C₄H₆Cl. This suggests that it could be a chloroalkane. The presence of a chlorine atom indicates that it is likely a substituted alkane.

2. **Consider Possible Structures**:
The possible structures for C₄H₆Cl include:
- Tertiary butyl chloride (C(CH₃)₃Cl)
- Secondary butyl chloride (C₂H₅CHClCH₃)
- Isobutyl chloride (C₃H₇CH₂Cl)
- Normal butyl chloride (C₃H₇CH₂Cl)

3. **Reaction with Sodium in Diethyl Ether**:
The reaction of alkyl halides with sodium in diethyl ether is known as the Wurtz reaction. This reaction typically leads to the formation of alkanes.

4. **Analyze Each Option**:
- **Tertiary butyl chloride**:
- Structure: (CH₃)₃CCl
- Wurtz Reaction: (CH₃)₃CCl + 2 Na → C₄H₁₀ + 2 NaCl
- Result: Produces a hydrocarbon (C₄H₁₀) which has a plane of symmetry and thus can only yield one monochlorinated derivative.

- **Secondary butyl chloride**:
- Structure: CH₃CHClCH₂CH₃
- Wurtz Reaction: Produces a hydrocarbon that has different types of hydrogen atoms leading to multiple monochlorinated derivatives.

- **Isobutyl chloride**:
- Structure: (CH₃)₂CHCH₂Cl
- Wurtz Reaction: Produces a hydrocarbon that also has different types of hydrogen atoms leading to multiple monochlorinated derivatives.

- **Normal butyl chloride**:
- Structure: CH₃CH₂CH₂CH₂Cl
- Wurtz Reaction: Produces a hydrocarbon that has different types of hydrogen atoms leading to multiple monochlorinated derivatives.

5. **Conclusion**:
The only compound that gives one monochlorinated derivative upon chlorination is **tertiary butyl chloride (C(CH₃)₃Cl)**.

### Final Answer:
The compound A is **tertiary butyl chloride**.

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