Is there any mechanism available for reduction of alkyl azides to amines. One of the reactions is conversion by $\ce{Na}$ in ethanol or by $\ce{LiAlH4}$. But how do these proceed? $\ce{LiAlH4}$ will produce a hydride ion which attacks where?

  • $\begingroup$ Different reagents will have different mechanisms. Are you interested in one reagent in particular? $\endgroup$
    – bon
    Commented Jul 16, 2015 at 17:20
  • 2
    $\begingroup$ the ones I have mentioned i.e. Na in ethanol and LAH $\endgroup$ Commented Jul 16, 2015 at 17:24

1 Answer 1


I googled it for a while and this was the best thing I found (Source):

This is a tough question, that is probably not known with any certainty. Even Jerry March (Adv Organic Chem, 4th ed, page 1219) doesn't commit himself to a mechanism.

You'll have to speculate. Add a hydride on the N next to the alkyl group, then grab a proton on the terminal N. Add a hydride on the terminal N, then grab a proton on the middle N. After that, it gets a little sketchy for breaking the N-N bond.

Try a SN2 attack by hydride on the middle N, giving hydrazine and RNH-, which is a lousy SN2 leaving group, but we're stuck with it. Protonation of the RNH- gives the amine and hydrazine. Or, you could do a SN2 on the N next to the alkyl group, and kick out a NH2NH- anion, which is also a lousy leaving group for the SN2. You can see why most books conveniently leave out a mechanism for this reduction.

  • $\begingroup$ I don't see the mechanism on that link. Which page are you referring to exactly? $\endgroup$
    – bon
    Commented Jul 18, 2015 at 18:09
  • $\begingroup$ At the current state, this doesn't provide an answer to the question. Am flagging for deletion. $\endgroup$
    – M.A.R.
    Commented Jul 18, 2015 at 18:23
  • $\begingroup$ This is a better one, but it's highly encouraged (read: required) that you put the link to the source here. $\endgroup$
    – M.A.R.
    Commented Jul 23, 2015 at 19:56
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    $\begingroup$ I'm finding answers.yahoo.com/question/index?qid=20100525170905AA9PDiD as a source $\endgroup$
    – austinian
    Commented Jul 23, 2015 at 21:20
  • 2
    $\begingroup$ If you are quoting verbatim, always mention the source. I will insert it for now since @austinian already found it, but please avoid that in future answers. $\endgroup$ Commented Jul 24, 2015 at 1:54

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