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March 25, 2017

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What is the major product formed on reaction of 1-pentene with bromine in aqueous solution?

a. 1-Bromo-1-pentanol
b. 1-Bromo-2-pentanol
c. 2-Bromo-1-pentanol
d. 1-Bromo-1-pentanol
e. 2-Bromo-1-pentene

  • organic chemistry - ,

    One bromine atom becomes attached to the first carbon in the first stage of the reaction. The 2nd carbon becomes positive and bond with a water molecule which then loses a proton to form a hydroxyl group.
    H2C=CHCH2CH2CH3 + Br2 --> BrH2C-CH(+)CH2CH2CH3 + Br-
    BrH2C-CH(+)CH2CH2CH3 + H2O --> BrH2C-CH(OH2+)CH2CH2CH3
    BrH2C-CH(OH2+)CH2CH2CH3 --> BrH2CCH(OH)CH2CH2CH3 + H+
    This should tell you which of the answers is my choice.

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