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When 3-methyl-2-butanol reacts with HBr,...

When 3-methyl-2-butanol reacts with HBr, 2-bromo-2-methylbutane is obtained as the only product. Why?

Text Solution

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In this reaction , a`2^(@)` carboncation is formed as an intermediate. Since `2^(@)` carbocation is less stable than `3^(@)` carbocation the `2^(@)` carbocation undergoes 2,3-hydride shift to produce `3^(@)` carbocation. Now `Br^(Theta)` ion (nucleophile) attacks the electrophilic centre of the `3^(@)` carbocation to produce 2-bromo-2-methybutane.
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Knowledge Check

  • Choose the reagent and reactant that would produce 2-methyl-2- butanol as a major product.

    A
    Only I
    B
    Only I, III
    C
    Only II and III
    D
    I ,II and III

  • Choose the reagent and reactant that would produce 2-methyl-2- butanol as a major product.

    A
    Only I
    B
    Only I, III
    C
    Only II and III
    D
    I ,II and III

  • 2-Methylbutane on reacting with Br_2 in presence of sunlight mainly gives

    A
    1-Bromo-2-methylbutane
    B
    2-Bromo-2- methylbutane
    C
    2-Bromo-3-methylbutane
    D
    1-Bromo-3- methylbutane
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