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Chemistry LibreTexts

Reductions

  • Page ID
    20918
  • Reduction Overview.png

    General Guidelines for Various Reducing Agents
    Hydride Donor Iminium Ion Acid Halide Aldehyde Ester Amide Carboxylic Salt
    LiAlH4 Amine Alcohol Alcohol

    Alcohol

    Amine Alcohol
    DIBAL-H Alcohol Alcohol

    Alcohol

    Aldehyde

    Amine

    Aldehyde

    Alcohol

    NaAlH(Ot-Bu)3

    (Red-Al)

    Aldehyde Alcohol

    Alcohol

    (slow)

    Amine

    (slow)

    AlH3 Alcohol Alcohol Alcohol Amine Alcohol
    NaBH4 Amine Alcohol –*
    NaCNBH3 Amine

    Alcohol

    (slow)

    Na(OAc)3BH Amine

    Alcohol

    (slow)

    Alcohol

    (slow)

    Amine

    (slow)

    B2H6 Alcohol Alcohol

    Alcohol

    (slow)

    Amine

    (slow)

    Alcohol

    Li(Et)3BH

    (Super Hydride)

    Alcohol Alcohol Alcohol Amine

    * α-alkoxy esters are reduced to the corresponding alcohol

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