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18.10: Nucleophilic Addition of Hydrazine (Wolff-Kishner Reaction)

Organic Chemistry · LibreTexts

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    From LibreTexts, under CC BY-NC-SA 4.0, as the source states it; its equations are written in TeX, which the PDF shows typeset. This page at LibreTexts.

    Aldehydes and ketones can be converted to a hydrazine derivative by reaction with hydrazine. These "hydrazones" can be further converted to the corresponding alkane by reaction with base and heat. These two steps can be combined into one reaction called the Wolff-Kishner Reduction which represents a general method for converting aldehydes and ketones into alkanes. Typically a high boiling point solvent, such as ethylene glycol, is used to provide the high temperatures needed for this reaction to occur. Note! Nitrogen gas is produced as part of this reaction.

    Reaction of Aldehydes or Ketones with Hydrazine Produces a Hydrazone

    1.jpg

    Reaction with a Base and Heat Converts a Hydrazone to an Alkane

    2.jpg

    Both Reactions Together Produces the Wolff-Kishner Reduction

    ch 19 sect 10 example 1.png

    The Wolff-Kishner reaction for cyclopentanone is shown below.

    ch 19 sect 10 example 2.png

    Mechanism of the Wolff-Kishner Reduction

    1) Deprotonation of Nitrogen

    5.jpg

    2) Protonation of the Carbon

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    3) Deprotonation of Nitrogen

    7.jpg

    4) Protonation of Carbon

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    Exercise

    17. Draw the products for the following reactions.

    ch 19 sect 10 exercise.png

    Answer

    17.

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    Contributors and Attributions

    18.10: Nucleophilic Addition of Hydrazine (Wolff-Kishner Reaction) is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts.