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CH3Br + NaNH2 reaction mechanisms?

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    Hi, wondering if can have a little help with a reaction mechanism,

    I have a 3 part question as part of homework, I think have got A) right and C)but really not sure about part B

    a) CH3CH2Br with the O atom of OH

    CH3CH2Br + OH ---> CH3CH2OH + Br

    b) Write out the reaction mechanism for CH3Br and NaNH2

    c) Propanal with H+ What is the product?
    Propan-1-ol ?
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    This is all about competition of the other reactant acting as a base or a nucleophile. In reality, it is often one which predominates and you can get some of the other reaction.

    For (b), NaNH2 is a great base. NH2 can abstract a proton releasing NH3, favourable in terms of entropy, etc. I have a feeling that Br would then leave, giving you a CH2 carbene.

    (c) Aldehyde propanal with H+ => well carbonyl in acid would tautomerise to give you the enol form, remember?

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Updated: February 28, 2011
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