An organic compound A`(C_(4)H_(9)Cl)` on the reaction with Na/diethly ether gives a hydrocarbon which on monochlorination gives only one chloro derivative then, A is

Options

A. t-butyl chloride
B. Secondary butyl chloride
C. Isobutyl chloride
D. n-butyl chloride

Answer

To solve the problem, we need to identify the organic compound A (C₄H₉Cl) that reacts with sodium in diethyl ether to yield a hydrocarbon, which upon monochlorination gives only one chloro derivative. Let's break it down step by step.

### Step 1: Analyze the molecular formula
The given molecular formula is C₄H₉Cl. This indicates that the compound contains 4 carbon atoms, 9 hydrogen atoms, and 1 chlorine atom.

**Hint:** Look for common structures that fit this molecular formula, particularly those that might lead to a single product upon monochlorination.

### Step 2: Identify possible structures
Considering the structure of C₄H₉Cl, we can think of different isomers. The most likely candidate that fits this formula and can lead to a single product upon chlorination is tertiary butyl chloride (C(CH₃)₃Cl), also known as 2-chloro-2-methylpropane.

**Hint:** Consider the branching in the carbon chain; branched structures often lead to fewer products upon chlorination.

### Step 3: Reaction with sodium in diethyl ether
When tertiary butyl chloride reacts with sodium in diethyl ether, it undergoes the Wurtz reaction. This reaction typically leads to the formation of alkanes by coupling two alkyl halides. In this case, the product would be 2,2-dimethylpropane (C₅H₁₂).

**Hint:** Remember that Wurtz reaction involves the coupling of alkyl halides, which can lead to the formation of larger alkanes.

### Step 4: Monochlorination of the hydrocarbon
The hydrocarbon formed (2,2-dimethylpropane) can undergo monochlorination. Since all the hydrogen atoms on the same carbon are equivalent, replacing any of these hydrogen atoms with chlorine will yield the same product. Therefore, only one chloro derivative will be formed, which is 1-chloro-2,2-dimethylpropane.

**Hint:** Monochlorination leads to only one product when all the hydrogen atoms being replaced are equivalent.

### Conclusion
Based on the analysis, the compound A (C₄H₉Cl) is tertiary butyl chloride (C(CH₃)₃Cl).

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

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