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Which of the following reaction follows ...

Which of the following reaction follows `S_N1` mechanism ?

A

`(CH_3)_3C - CH_2Cl+CH_3OK`

B

`(CH_3)_2CHCH_2Cl+KCN`

C

`(CH_3)_3C-Cl+NaOH(aq).`

D

`(CH_3)_2CHI+H_2O`

Text Solution

AI Generated Solution

The correct Answer is:
To determine which reaction follows the \( S_N1 \) mechanism, we need to understand the characteristics of the \( S_N1 \) mechanism and the stability of carbocations formed during the reaction. ### Step-by-Step Solution: 1. **Understanding the \( S_N1 \) Mechanism**: - The \( S_N1 \) (Substitution Nucleophilic Unimolecular) mechanism involves two main steps: 1. Formation of a carbocation intermediate by the dissociation of the leaving group (e.g., halide). 2. Nucleophilic attack on the carbocation. - The rate of the reaction depends only on the concentration of the substrate (alkyl halide), hence it is unimolecular. 2. **Stability of Carbocations**: - The stability of carbocations is crucial for the \( S_N1 \) mechanism. The order of stability is: - Tertiary (3°) > Secondary (2°) > Primary (1°) > Methyl (0°). - More stable carbocations are more likely to form and thus favor the \( S_N1 \) mechanism. 3. **Analyzing the Given Options**: - We will analyze each option to determine the type of carbocation formed upon dissociation. **Option 1**: \( \text{(CH}_3)_3C\text{Cl} \) - Upon dissociation, it forms a tertiary carbocation \( \text{(CH}_3)_3C^+ \). - This is a stable carbocation, favoring the \( S_N1 \) mechanism. **Option 2**: \( \text{CH}_3\text{CH}_2\text{Cl} \) - Upon dissociation, it forms a primary carbocation \( \text{CH}_3\text{CH}_2^+ \). - This is a less stable carbocation, not favoring the \( S_N1 \) mechanism. **Option 3**: \( \text{(CH}_3)_2\text{CHCl} \) - Upon dissociation, it forms a secondary carbocation \( \text{(CH}_3)_2\text{CH}^+ \). - This is a moderately stable carbocation, which can undergo \( S_N1 \) but is not as favorable as a tertiary carbocation. **Option 4**: \( \text{CH}_3\text{CH}_2\text{CH}_2\text{Cl} \) - Upon dissociation, it forms a primary carbocation \( \text{CH}_3\text{CH}_2\text{CH}_2^+ \). - This is also a less stable carbocation, not favoring the \( S_N1 \) mechanism. 4. **Conclusion**: - The only option that forms a stable carbocation and thus follows the \( S_N1 \) mechanism is **Option 1**: \( \text{(CH}_3)_3C\text{Cl} \). ### Final Answer: **Option 1: \( \text{(CH}_3)_3C\text{Cl} \)** follows the \( S_N1 \) mechanism.
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Knowledge Check

  • Which of the following reaction follows S_(N^(1)) mechanism ?

    A
    `(CH_(3))_(3)C-CH_(2)Cl+CH_(3)OK`
    B
    `(CH_(3))_(2)CHCH_(2)Cl+KCN`
    C
    `(CH_(3))_(3)C-Cl+NaOH`
    D
    `(CH_(3))_(2)CHl+H_(2)O`
  • Which of the following reactions follows concerted mechanism ?

    A
    `S_(N)1`
    B
    `S_(N)2`
    C
    `E_(1)`
    D
    `E_(2)`
  • The following reaction proceeds by which mechanism ?

    A
    `S_(N)1`
    B
    `S_(N)2`
    C
    E2
    D
    E1
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