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Why does LiAl4/NH4Cl on an amide not produce a secondary alcohol?

Discussion in 'MCAT Study Question Q&A' started by csx, Sep 5, 2014.

  1. csx

    csx
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    rather is just gets completely reduced....why?
     
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  3. fakedoctor123

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    Usually, if you use LiAlH4 to reduce any carboxylic acid derivative, you will get its respective alcohol. However, one exception is for amides because when you try to reduce the amide using LAH, the NH2 is a horrible leaving group, and it can't leave. Thus, the OH leaves instead and you form an amine.
     
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