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    Mechanism of esterification and hydrolysis using O18 isotope

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    1. If you look at a reaction for an esterification reaction, you cannot tell where the oxygen comes from (acid or alcohol). Draw the mechanism of this reaction, and devise an experiment using the mechanism and O18 (O18 isotope) to help prove unequivocally where the oxygen comes from.

    2. The Fischer Esterification is highly reversible. State two procedures performed in the reaction

    Isopentyl alcohol + Acetic acid ---H2SO4---> Isopentyl acetate

    that will help drive the reaction to the right.

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    Solution Preview

    The number of distinct mechanisms by which esterification of an acid or the hydrolysis of an ester proceeds and is due to three reasons:
    1. Esterification and hydrolysis may proceed either through an acyl oxygen (-C-O-/-R) or an alkyl- oxygen cleavage (-O-/-R)
    2. Hydrolysis of an ester may be accomplished either by acids or alkalis and depending upon the reagent, the species undergoing ...

    Solution Summary

    The number of distinct mechanisms by which esterification of an acid or the hydrolysis of an ester proceeds and is due to three reasons:
    1. Esterification and hydrolysis may proceed either through an acyl oxygen (-C-O-/-R) or an alkyl- oxygen cleavage (-O-/-R)
    2. Hydrolysis of an ester may be accomplished either by acids or alkalis and depending upon the reagent, the species undergoing hydrolysis may be a neutral ester molecule ( R-COOR') or an ionic conjugate acid (RCOOHR)+.
    3. The esterification and hydrolysis may proceed either by a unimolecular or a bimolecular mechanism.

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