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reduction of nitrile

Discussion in 'DAT Discussions' started by joonkimdds, Dec 26, 2008.

  1. joonkimdds

    joonkimdds Senior Member
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    In road map, nitrile is reduced to C-NH2 when LiAlH4, Et2O, and H2O are used.

    In #73, nitrile is reduced to C-NH2 and the reagent used was LiAlH4, Et2O then H3O+ (instead of H2O)

    The explanation says LiAlH4 with H2O is good way to blow yourself up.

    There was LiAlH4, H2O for a choice but this isn't the answer (probably because Et2O) is not present.

    My question is
    is it ok to use H3O+ in place of H2O? and if the answer is yes, is it just for this reaction or can H3O work just like H2O in any other reactions?
     
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  2. doc3232

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    LiAlH4 is basically a Hydrogen with 2 electrons looking for anything to bind to. In water, it will come across many Hydrogens to bind to (and make H2 gas). In acidic water (H3O+), it will come across MORE Hydrogen atoms....wait, never mind. Just read the question, it says LAH, ether THEN H3O+. You got me there joonkim ;)
     
  3. gentile1225

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    i'm pretty sure H2O and H30+ can be interchangeably when used with LiAlH4. I think its because water can act as an acid/base so using water instead of H30+ wont make a difference.
     
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  4. doc3232

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    Man...I misread EVERYTHING. HAHAHAHAHA. H2O can act as a acid as previous poster said instead of H3O.
     

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