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Organic Chem

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what is the equation including the mechanism for the reaction of 1-butanol with NaCl+ NaBr in H2S04

What are the equations for the side reactions?

  • Organic Chem -

    I think that they are trying to get you to look at this as an SN1 reaction. So for the mechanism see

    http://en.wikipedia.org/wiki/SN1_reaction

    When the CH3(CH2)2(CH2)+ species is genreated there are a number of possible outcomes. It is not the most stable carbocation that can be formed so it could form a more stable secondary carbocation by migration of an H from C-2 to C-1 to give
    CH3(CH2)(CH)+CH3. The carbon chain could also rearrange to give a tertiary carbocation which is more stable.

    (CH3)3C+

    A competing side reaction
    could be elimination to give

    CH3(CH2)CH=(CH2)

    similarly the secondary carbocation could form either of the alkenes

    CH3(CH2)(CH)+CH3 ->

    CH3(CH2)CH=(CH2) and/or
    CH3CH=CHCH3

    The ratio of the various possible products will depend on the conditions.

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