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Diol reagent question

  1. Jun 7, 2014 #1
    1. The problem statement, all variables and given/known data

    But-2-ene-1,4-diol is converted in two steps through an intermediate X into ketobutanedioic acid.
    Hot acidified KMnO4 is added in step 2.

    HOCH2CH=CHCH2OH ----> X -----> HO2CCOCH2CO2H

    What could be the reagent for step 1 and the intermediate X?

    reagent for step 1
    X
    A cold acidified KMnO4
    HOCH2CH2CH(OH)CH2OH ​
    B hot acidified KMnO4 O
    HCCH(OH)CH2CHO​
    C steam and concentrated
    H2SO4 HOCH2CH(OH)CH2CH2OH ​
    D warm acidified K2Cr2O7
    HO2CCH=CHCO2H​

    Sorry about the unalignment.

    3. The attempt at a solution
    I'm aware that an alkene reacts with cold KMnO4 to give a dol and hot KMnO4 to give a dicarboxylic acid but I'm stumped since the first compound is both a diol and alkene. Any help appreciated!
     
  2. jcsd
  3. Jun 8, 2014 #2
    Hi suitcasespeake! Welcome to PF! :smile:

    I suppose your C option is steam and concentrated ##H_2SO_4##, right?

    It is easy to solve the problem by eliminating the options. Do you see which options are not possible?
     
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