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    Haven't done this since AS and need some help.

    I have to convert Propene into:

    a.) CH3CH(OH)CH3 - Add HCl followed by NaOH
    b.) CH3COCH3 - Heat part a under eflux with dilute sulfuric acid and potassium dichromate VI
    c.) CH3C(OH)(CN)CH3 - add KCN and HCN to part b at pH 8
    d.) (CH3)2CHCN - ??? All I need to do here is replace the hydroxyl group in part C with a Hydrogen and forgot how to do that
    e.) (CH3)2CHCH2NH2 - Part d + LiAlH4 in dry ether and then hydrolyse with sulfuric acid
    f.) CH3CH(OH)CH2OH - Really stumped by this one :confused:

    Any help on part d and f will be appreciated.
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    (Original post by chaz1992)
    Haven't done this since AS and need some help.

    I have to convert Propene into:

    a.) CH3CH(OH)CH3 - Add HCl followed by NaOH
    b.) CH3COCH3 - Heat part a under eflux with dilute sulfuric acid and potassium dichromate VI
    c.) CH3C(OH)(CN)CH3 - add KCN and HCN to part b at pH 8
    d.) (CH3)2CHCN - ??? All I need to do here is replace the hydroxyl group in part C with a Hydrogen and forgot how to do that
    e.) (CH3)2CHCH2NH2 - Part d + LiAlH4 in dry ether and then hydrolyse with sulfuric acid
    f.) CH3CH(OH)CH2OH - Really stumped by this one :confused:

    Any help on part d and f will be appreciated.
    (f) this is a dihydroxylation. You can use,
    http://www.organic-chemistry.org/syn...1O/diols2.shtm

    (d) is simpler than you thought. add HCN across alkene, simple markovnikov rule puts H on the terminal alkene leaving you secondary carbocation and CN- adds in.
    Going from (c) to (d) is hard because cyanohydrin(species in c) is reversible with the keto form in acid, so not really a good starting point.
 
 
 
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