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When but -3-en-2-ol reacts with aq HBr ,...

When but `-3-en-2-ol` reacts with `aq HBr` , we get

A

3 - bromobut -1- ene

B

1 - bromobut -2- ene

C

a mixture of both A and B

D

2 - bromobut -2- ene

Text Solution

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The correct Answer is:
To solve the problem of what happens when but-3-en-2-ol reacts with aqueous HBr, let's break it down step by step. ### Step 1: Understand the Structure of But-3-en-2-ol But-3-en-2-ol has four carbon atoms, with a double bond between the 3rd and 4th carbon and a hydroxyl (OH) group on the 2nd carbon. The structure can be represented as follows: ``` CH3-CH=CH-CH2OH ``` ### Step 2: Reaction with Aqueous HBr When but-3-en-2-ol reacts with aqueous HBr, the HBr dissociates into H⁺ and Br⁻ ions. The H⁺ ion will attack the hydroxyl (OH) group, leading to the formation of a carbocation. ### Step 3: Formation of Carbocation The reaction will lead to the protonation of the alcohol group, resulting in the following structure: ``` CH3-CH=CH-CH2OH → CH3-CH=CH-CH2^+ (carbocation) ``` ### Step 4: Carbocation Stability and Rearrangement The carbocation formed can undergo rearrangement due to its stability. The positive charge can shift to the adjacent carbon, allowing for resonance stabilization: ``` CH3-CH^+-CH=CH2 → CH3-CH=CH-CH2^+ ``` ### Step 5: Nucleophilic Attack by Br⁻ The Br⁻ ion will attack the carbocation, leading to the formation of two possible products due to the two different carbocations formed during the reaction: 1. **3-Bromobut-1-ene**: - Formed when Br⁻ attacks the carbocation at the 3rd carbon. - Structure: ``` CH3-CH=CH-Br-CH2 ``` 2. **1-Bromobut-2-ene**: - Formed when Br⁻ attacks the carbocation at the 1st carbon. - Structure: ``` CH3-CH2-CH=CH-Br ``` ### Step 6: Naming the Products The products can be named as follows: - The first product is **3-bromobut-1-ene**. - The second product is **1-bromobut-2-ene**. ### Conclusion Thus, the reaction of but-3-en-2-ol with aqueous HBr yields two products: **3-bromobut-1-ene** and **1-bromobut-2-ene**.
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Knowledge Check

  • 3-methyl-pent-2-ene on reaction with HBr in the presence of peroxide forms an addition product. The number of possible stereoisomers for the product is

    A
    two
    B
    four
    C
    six
    D
    zero
  • The product formed when but-1-ene is subjected to HBr in the presence of peroxide is

    A
    1-bromobutane
    B
    2-bromobutane
    C
    1, 1-dibromobutane
    D
    1, 2-dibromobutane.
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