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The compound which forms one monochloro ...

The compound which forms one monochloro product, when treated with chlorine is

A

n-pentane

B

neo-pentane

C

2,2 dimethylpropane

D

Both (2) and (3)

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem of identifying the compound that forms only one monochloro product when treated with chlorine, we will analyze the given options step by step. ### Step-by-Step Solution: 1. **Understanding the Reaction**: - The reaction of hydrocarbons with chlorine (Cl2) in the presence of sunlight leads to a free radical substitution reaction. This means that chlorine can replace hydrogen atoms in the hydrocarbon. 2. **Analyzing n-Pentane**: - n-Pentane has the structure: CH3-CH2-CH2-CH2-CH3. - When treated with Cl2, chlorine can replace hydrogen atoms at different positions: - If Cl replaces a hydrogen at the 1st carbon: CH2Cl-CH2-CH2-CH2-CH3 (1-chloropentane) - If Cl replaces a hydrogen at the 2nd carbon: CH3-CHCl-CH2-CH2-CH3 (2-chloropentane) - If Cl replaces a hydrogen at the 3rd carbon: CH3-CH2-CHCl-CH2-CH3 (3-chloropentane) - If Cl replaces a hydrogen at the 4th carbon: CH3-CH2-CH2-CHCl-CH3 (4-chloropentane) - This results in **4 different monochloro products**. Therefore, n-pentane does not meet the criteria. 3. **Analyzing Neopentane**: - Neopentane has the structure: (CH3)4C (or C(CH3)4). - All four methyl groups are equivalent, meaning that chlorine can only replace one of the hydrogen atoms attached to the central carbon. - The product formed will be the same regardless of which methyl group is substituted: CH3-C(CH3)3Cl. - This results in **only 1 monochloro product**. Therefore, neopentane meets the criteria. 4. **Analyzing 2,2-Dimethylpropane**: - 2,2-Dimethylpropane has the structure: CH3-C(CH3)2-CH3. - Similar to neopentane, the two methyl groups on the second carbon are equivalent, and chlorine can only replace one of the hydrogen atoms attached to the central carbon. - The product formed will be the same regardless of which methyl group is substituted: CH3-C(CH3)2Cl. - This results in **only 1 monochloro product**. Therefore, 2,2-dimethylpropane also meets the criteria. 5. **Conclusion**: - Both neopentane and 2,2-dimethylpropane form only one monochloro product when treated with chlorine. Thus, the correct answer is that both options 2 (neopentane) and 3 (2,2-dimethylpropane) are correct. ### Final Answer: The compound which forms one monochloro product when treated with chlorine is **both 2 and 3 (neopentane and 2,2-dimethylpropane)**.
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