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    The document summarizes common reactions of nitrile groups: 1) Hydrolysis of nitriles produces carboxylic acids and ammonia or ammonium ions depending on the conditions used. 2) Alkylation of nitriles using organometallic reagents such as organolithium or Grignard reagents forms ketones, stopping at the ketone product. 3) Reduction of nitriles can produce either primary amines, using sodium borohydride or lithium aluminum hydride, or aldehydes using a less reactive reducing agent like DIBAL-H.

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    nitrile rxns

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    The document summarizes common reactions of nitrile groups: 1) Hydrolysis of nitriles produces carboxylic acids and ammonia or ammonium ions depending on the conditions used. 2) Alkylation of nitriles using organometallic reagents such as organolithium or Grignard reagents forms ketones, stopping at the ketone product. 3) Reduction of nitriles can produce either primary amines, using sodium borohydride or lithium aluminum hydride, or aldehydes using a less reactive reducing agent like DIBAL-H.

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    812 views1 page

    Nitrile Rxns

    Uploaded by

    api-465421809
    The document summarizes common reactions of nitrile groups: 1) Hydrolysis of nitriles produces carboxylic acids and ammonia or ammonium ions depending on the conditions used. 2) Alkylation of nitriles using organometallic reagents such as organolithium or Grignard reagents forms ketones, stopping at the ketone product. 3) Reduction of nitriles can produce either primary amines, using sodium borohydride or lithium aluminum hydride, or aldehydes using a less reactive reducing agent like DIBAL-H.

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    CA DERIVATIVES NITRILE RXNS Chemistry Specialist: Alicia Hart

    UC Davis - SASC
    a) Hydrolysis
    O

    R C N H+
    H2O, R OH NH4+

    O
    NaOH
    H2O,
    R O NH3

    b) Alkylation
    i) Organometallic Reagents
    O

    R C N 1. R"Li or R"MgX, Ether NH4+


    2. H3O+ R R"
    - given 2 eq. of the organometallic reagent, will NOT do alkylation twice; stops at ketone.

    c) Reduction
    NaBH4, EtOH
    NR

    NH2
    1. LiAlH 4, THF
    2. H3O+
    R C N
    or H , Pt
    2 R H
    H O

    To stop at aldehyde, 1. DIBAH, THF


    use less reactive red. agent...
    2. H3O+ R H NH4+
    - Note: DIBAH is aka DIBAL-H and stands for diisobutyl aluminium hydride.

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