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1-bromobutane conversion work shown please help!

  1. Feb 18, 2009 #1
    equations used to convert 1-bromobutane to:

    a.) CH3CH2CH2CH2D

    b.) octane

    c.) 1-butyne

    d.) CH3CH2CH2CH2CN

    e.) CH3CH2CH2CH2-O-C-(=O)-CH3


    work shown below:

    c.) 1-butyne

    CH3CH2CH2CH2Br => {(CH3)3COH, (CH3)3COK} =>CH3CH2CH=CH2
    CH3CH2CH=CH2 => {Br2} => CH3CH2CHBrCH2Br
    CH3CH2CHBrCH2Br => {NaNH2, NH3} => CH3CH2C(bondx3)C(-)Na(+)
    CH3CH2C(bondx3)C(-)Na(+) => {H2O} => CH3CH2C(bondx3)CH

    d.) CH3CH2CH2CH2CN
    CH3CH2CH2Br + NaCN --> CH3CH2CH2CH2CN + NaBr

    5. CH3CH2CH2CH2-O-C(=O)CH3

    CH3CH2CH2CH2Br + CH3C(=O)OH

    I need help with a.) and b.) I don't know how to extend the alkyl halide to an octane, and exchange the Br with D for a)

    please help me...
     
  2. jcsd
  3. Feb 26, 2009 #2

    chemisttree

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    What would happen if you were to quench a carbanion with D20 or D3O+?

    and

    Review Wurtz coupling.
     
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