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Which of the following alkyl halides is ...

Which of the following alkyl halides is hydrolysed by `S_(N^1)`mechanism ?
`CH_3 Cl`
`CH_3 CH_2 Cl`
`CH_3CH_2 CH_2 Cl`
`(CH_3)_3 C Cl`

A

`CH_3 Cl`

B

`CH_3 CH_2 Cl`

C

`CH_3CH_2 CH_2 Cl`

D

`(CH_3)_3 C Cl`

Text Solution

AI Generated Solution

The correct Answer is:
To determine which of the given alkyl halides is hydrolyzed by the \( S_N1 \) mechanism, we need to analyze the stability of the carbocations formed from each alkyl halide. The \( S_N1 \) mechanism involves the formation of a carbocation intermediate, and the stability of this carbocation is crucial for the reaction to proceed. ### Step-by-Step Solution: 1. **Identify the Alkyl Halides**: We have four alkyl halides to consider: - \( CH_3Cl \) (Methyl chloride) - \( CH_3CH_2Cl \) (Ethyl chloride) - \( CH_3CH_2CH_2Cl \) (Propyl chloride) - \( (CH_3)_3CCl \) (Tert-butyl chloride) 2. **Draw the Carbocations**: - For \( CH_3Cl \): - Hydrolysis gives \( CH_3^+ \) (methyl carbocation), which is a primary (1°) carbocation. - For \( CH_3CH_2Cl \): - Hydrolysis gives \( CH_3CH_2^+ \) (ethyl carbocation), which is also a primary (1°) carbocation. - For \( CH_3CH_2CH_2Cl \): - Hydrolysis gives \( CH_3CH_2CH_2^+ \) (propyl carbocation), which is a primary (1°) carbocation. - For \( (CH_3)_3CCl \): - Hydrolysis gives \( (CH_3)_3C^+ \) (tert-butyl carbocation), which is a tertiary (3°) carbocation. 3. **Analyze Carbocation Stability**: - The stability of carbocations increases with the degree of substitution: - Tertiary (3°) > Secondary (2°) > Primary (1°) > Methyl (0°). - The methyl, ethyl, and propyl carbocations are all primary and less stable compared to the tert-butyl carbocation. 4. **Determine the \( S_N1 \) Mechanism**: - Since \( S_N1 \) reactions favor the formation of more stable carbocations, the only alkyl halide that can undergo hydrolysis via the \( S_N1 \) mechanism is the one that forms a tertiary carbocation. - Therefore, \( (CH_3)_3CCl \) (tert-butyl chloride) is the alkyl halide that is hydrolyzed by the \( S_N1 \) mechanism. ### Final Answer: The alkyl halide that is hydrolyzed by the \( S_N1 \) mechanism is \( (CH_3)_3CCl \).

To determine which of the given alkyl halides is hydrolyzed by the \( S_N1 \) mechanism, we need to analyze the stability of the carbocations formed from each alkyl halide. The \( S_N1 \) mechanism involves the formation of a carbocation intermediate, and the stability of this carbocation is crucial for the reaction to proceed. ### Step-by-Step Solution: 1. **Identify the Alkyl Halides**: We have four alkyl halides to consider: - \( CH_3Cl \) (Methyl chloride) - \( CH_3CH_2Cl \) (Ethyl chloride) - \( CH_3CH_2CH_2Cl \) (Propyl chloride) ...
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