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    Esterfication Mechanism

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    rasikamuhandiramge
    Esterification reactions involve the reaction of carboxylic acids and alcohols to form esters. Specific examples provided are the reactions of acetic acid with ethanol to form ethyl acetate, and benzoic acid with methanol to form methyl benzoate. Esterification reactions reach equilibrium within a few hours when catalyzed by a strong acid like sulfuric acid or hydrogen chloride. The yield of the ester can be increased by using an excess of either the acid or alcohol, and by removing water from the reaction mixture as it is formed.

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    Esterfication Mechanism

    Uploaded by

    rasikamuhandiramge
    39 views1 page
    Esterification reactions involve the reaction of carboxylic acids and alcohols to form esters. Specific examples provided are the reactions of acetic acid with ethanol to form ethyl acetate, and benzoic acid with methanol to form methyl benzoate. Esterification reactions reach equilibrium within a few hours when catalyzed by a strong acid like sulfuric acid or hydrogen chloride. The yield of the ester can be increased by using an excess of either the acid or alcohol, and by removing water from the reaction mixture as it is formed.

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    Esterification reactions involve the reaction of carboxylic acids and alcohols to form esters. Specific examples provided are the reactions of acetic acid with ethanol to form ethyl acetate, and benzoic acid with methanol to form methyl benzoate. Esterification reactions reach equilibrium within a few hours when catalyzed by a strong acid like sulfuric acid or hydrogen chloride. The yield of the ester can be increased by using an excess of either the acid or alcohol, and by removing water from the reaction mixture as it is formed.

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    39 views1 page

    Esterfication Mechanism

    Uploaded by

    rasikamuhandiramge
    Esterification reactions involve the reaction of carboxylic acids and alcohols to form esters. Specific examples provided are the reactions of acetic acid with ethanol to form ethyl acetate, and benzoic acid with methanol to form methyl benzoate. Esterification reactions reach equilibrium within a few hours when catalyzed by a strong acid like sulfuric acid or hydrogen chloride. The yield of the ester can be increased by using an excess of either the acid or alcohol, and by removing water from the reaction mixture as it is formed.

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    of 1

    17.

    7 Esters 779

    Specific Examples
    O O
    HA
    + EtOH + H 2O
    OH OEt
    Acetic acid Ethanol Ethyl acetate

    O O
    HA
    + MeOH + H2O
    OH OMe

    Benzoic acid Methanol Methyl benzoate

    Fischer esterifications reach equilibrium within a matter of a few hours when an acid and
    an alcohol are refluxed with a small amount of concentrated sulfuric acid or hydrogen
    chloride. They proceed very slowly in the absence of a strong acid catalyst. Since the
    position of equilibrium controls the amount of the ester formed, the use of an excess of
    either the carboxylic acid or the alcohol increases the yield based on the limiting reagent.
    Just which component we choose to use in excess will depend on its availability and cost.
    The yield of an esterification reaction can also be increased by removing water from the
    reaction mixture as it is formed.
    When benzoic acid reacts with methanol that has been labeled with 18O, the labeled
    oxygen appears in the ester. This result reveals just which bonds break in the esterification:
    O O
    18 HA
    + Me O H 18 + H2O
    OH OMe

    The results of the labeling experiment and the fact that esterifications are acid catalyzed
    are both consistent with the mechanism shown in the box below. This mechanism is typi-
    cal of acid-catalyzed nucleophilic addition–elimination reactions at acyl carbon atoms.

    [ A Mechanism for the Reaction Acid-Catalyzed Esterification


    [
    + H
    H—O—H O O+ H O H
    +CH 3 OH
    H C C +
    C6H5 C O CH3
    C6H5 O H C6H5 O H – CH 3 OH
    O H

    The carboxylic acid The alcohol attacks the A proton is lost at


    accepts a proton from protonated carbonyl one oxygen atom
    the strong acid catalyst. group to give a and gained at another.
    tetrahedral intermediate.

    H O
    H
    H O H O+ O
    –H3O+
    C6H5 C O CH3 C C
    +H3O+ C6H5 O
    C6H5 O CH3 CH3
    O+ H
    H
    Loss of a molecule of water Transfer of a proton to
    gives a protonated ester. a base leads to the ester.

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