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    Cannizzaro Reaction

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    In an experiment, benzaldehyde reacts with potassium hydroxide to produce benzoate and benzyl alcohol. (Cannizzaro Reaction)

    a) What is the overall balanced equation?
    b) How does sodium bisulphite remove the unchanged benzaldehyde from the reaction mixture?
    c) In mechanism 1(attached), a hydride ion is transferred, how can this be proven experimentally?
    d) In mechanism 2 (attached) using curved arrows to symbolize the flow of electrons, write the mechanism for the hydride transfer from NADH to a carbonyl compound. your mechanism should show NADH becomes NAD+.

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    Solution Preview

    a) 2RCHO --- base ---> RCOO- + RCH2OH
    where the base is potassium hydroxide and R is the benzyl group (C6H5---).

    b) Sodium bisulfite removes the unchanged benzaldehyde ...

    Solution Summary

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