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The reaction of propene with HOCI (CI(2)...

The reaction of propene with `HOCI (CI_(2)+H_(2)O)` proceeds through the intermediate:

A

`CH_(3)-CHCl-CH_(2)^(+)`

B

`CH_(3)-CH^(+)-CH_(2)-OH`

C

`CH_(3)-CH^(+)-CH_(2)-Cl`

D

`CH_(3)-CH(OH)-CH_(2)^(+)`

Text Solution

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The correct Answer is:
To determine the intermediate formed in the reaction of propene with HOCl, we can follow these steps: ### Step-by-Step Solution: 1. **Identify the Reactants**: - The reactant is propene, which has the structure CH₃-CH=CH₂. 2. **Understanding HOCl**: - HOCl can dissociate into OH⁻ (hydroxide ion) and Cl⁺ (chloronium ion). The chlorine atom in HOCl acts as an electrophile due to its positive charge. 3. **Electrophilic Attack**: - The Cl⁺ ion can attack the double bond in propene. The double bond has electron density, making it a site for electrophilic attack. - The attack can occur at either of the two carbon atoms involved in the double bond. 4. **Formation of Carbocation**: - If Cl⁺ attacks the first carbon (C1), the positive charge will be on the second carbon (C2), forming a primary carbocation: CH₃-CH(Cl)-CH₂⁺. - If Cl⁺ attacks the second carbon (C2), the positive charge will be on the first carbon (C1), forming a secondary carbocation: CH₂⁺-CH-CH₃. 5. **Stability of Carbocations**: - Secondary carbocations are more stable than primary carbocations due to hyperconjugation and inductive effects. Therefore, the attack at C2 leading to a secondary carbocation is preferred. 6. **Formation of the Intermediate**: - The stable secondary carbocation formed is CH₂⁺-CH-CH₃ (with Cl attached to C2). This carbocation is the intermediate in the reaction. 7. **Final Product Formation**: - The hydroxide ion (OH⁻) can then attack the carbocation to form the final product, which is CH₃-CH(Cl)-CH₂OH. ### Conclusion: The intermediate formed in the reaction of propene with HOCl is a secondary carbocation.
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Knowledge Check

  • The reaction of propene with H_(3)O^(+) will proceed with which of the following intermediates ?

    A
    B
    C
    D
  • , this reaction proceed through :

    A
    electrophilic addition
    B
    benzyne intermediate
    C
    nucleophilic aromatic substitution
    D
    oxirane
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