Reagents required for chemical conversion?

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  • 2-bromo-3-methylbutane is converted to 2-bromo-2-methylbutane in 2 steps. Which reagents would you use to achieve this conversion?
    a. Reagent A is Br2 and reagent B is H2/Pd catalyst
    b. Reagent A is H2SO4 and reagent B is H2/Pd catalyst
    c. Reagent A is hot KMnO4 and reagent B is Br2
    d. Reagent A is B2H6 followed by H2O2/OH and reagent B is NaOH(aq)
    e. Reagent A is NaOH in ethanol and reagent B is HBr

    I have no idea. Please help? This is a really tough one...


  • I think the answer is e.
    First NaOH/ethanol will convert 2-bromo-3-methylbutane to 2-hydroxy-3-methylbutane.
    CH3-CH(Br)-CH(CH3)-CH3 + OH-/alc ---> CH3-CH(OH)-CH(CH3)-CH3,
    then
    CH3-CH(OH)-CH(CH3)-CH3 + HBr ---> CH3-CH(+)-CH(CH3)-CH3 + Br-
    CH3-CH(+)-CH(CH3)-CH3 ----> CH3-CH2-CH(+)(CH3)-CH3 (rearrangement)
    CH3-CH2-CH(+)(CH3)-CH3 + Br- ---->
    CH3-CH2-CH(Br)(CH3)-CH3








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