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    Ester Rxns

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    1) This document summarizes common reactions of carboxylic acid derivatives including hydrolysis, alcoholysis, ammonolysis, alkylation, and reduction. 2) Hydrolysis involves adding water to cleave the ester bond and form an alcohol and carboxylic acid. Alcoholysis involves exchanging one alcohol for another in a transesterification reaction. 3) Ammonolysis uses ammonia to cleave the ester, forming an amide and alcohol. Alkylation can use organometallic or alkyl halide reagents to add alkyl groups. Reduction can use sodium borohydride or lithium aluminum hydride to reduce esters to alcohols or al

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    Ester Rxns

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    844 views1 page
    1) This document summarizes common reactions of carboxylic acid derivatives including hydrolysis, alcoholysis, ammonolysis, alkylation, and reduction. 2) Hydrolysis involves adding water to cleave the ester bond and form an alcohol and carboxylic acid. Alcoholysis involves exchanging one alcohol for another in a transesterification reaction. 3) Ammonolysis uses ammonia to cleave the ester, forming an amide and alcohol. Alkylation can use organometallic or alkyl halide reagents to add alkyl groups. Reduction can use sodium borohydride or lithium aluminum hydride to reduce esters to alcohols or al

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    ester rxns

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    1) This document summarizes common reactions of carboxylic acid derivatives including hydrolysis, alcoholysis, ammonolysis, alkylation, and reduction. 2) Hydrolysis involves adding water to cleave the ester bond and form an alcohol and carboxylic acid. Alcoholysis involves exchanging one alcohol for another in a transesterification reaction. 3) Ammonolysis uses ammonia to cleave the ester, forming an amide and alcohol. Alkylation can use organometallic or alkyl halide reagents to add alkyl groups. Reduction can use sodium borohydride or lithium aluminum hydride to reduce esters to alcohols or al

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    844 views1 page

    Ester Rxns

    Uploaded by

    api-465421809
    1) This document summarizes common reactions of carboxylic acid derivatives including hydrolysis, alcoholysis, ammonolysis, alkylation, and reduction. 2) Hydrolysis involves adding water to cleave the ester bond and form an alcohol and carboxylic acid. Alcoholysis involves exchanging one alcohol for another in a transesterification reaction. 3) Ammonolysis uses ammonia to cleave the ester, forming an amide and alcohol. Alkylation can use organometallic or alkyl halide reagents to add alkyl groups. Reduction can use sodium borohydride or lithium aluminum hydride to reduce esters to alcohols or al

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    CA DERIVATIVES ESTER RXNS Chemistry Specialist: Alicia Hart

    UC Davis - SASC
    a) Hydrolysis
    O O
    H+ or NaOH
    H2O,
    R OR' R OH R'OH

    b) Alcoholysis - Transesterification

    O O

    H+ or NaOR"
    R"OH,
    R OR' R OR" R'OH

    c) Ammonolysis/Aminolysis
    O O

    NH3
    R OR' R NH2 R'OH

    d) Alkylation
    i) Organometallic Reagents
    OH
    O

    1. R"Li or R"MgX, Ether


    R R" R'OH
    R OR' 2. H3O+ R"
    - given 2 eq. of the organometallic reagent, does alkylation twice by kicking off the OR' and reforming the carbonyl.

    ii) Alkylation
    O O

    R 1. LDA, THF R
    OR' 2. R"X OR'
    R"
    e) Reduction
    NaBH4
    NR
    EtOH

    O OH
    1. LiAlH 4, ether R'OH
    2. H3O+
    R OR' R H
    H O

    To stop at aldehyde, 1. DIBAH, Ether


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

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