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8 Cards in this Set
- Front
- Back
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What is a useful method for turning an aldehyde or ketone into an alkene, R2C=0 ~~> R2CH2
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Wolff-Kishner Rxn
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A Wolff-Kishner Rxn was orginally carried out at temp as high as 240C, but a modification in which dimethyl sulfoxide is used as solvent allows the process..
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to take place near room temp.
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The Wolff-Kishner Rxn involves formation of a hydrazone intermediate, R2C=NNH2, followed by ...
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base-catalyzed double-bond migration, loss of N2 gas, and protonation to give the alkane product
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The double-bond migration of a Wolff-Kishner Rxn takes place when ...
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the base removes a of the weakly acidic NH protons to generate a hydrozone anion
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Since the hydrazone anion of the Wolff-Kishner Rxn
has an allylic reasonance structure that places the double bond btwn nitogens and the negative charge on carbon, ... |
reprotonation can occur on carbon to generate the double bond rearrangement product
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The loss of nitrogen and formation of an alkyl anion of a Wolff-Kishner Rxn
- is driven by .. |
the large thermodynamic stability of the N2 molecule
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The Wolff-Kishner reduction accomplishes the same overall transformation as the catalytic hydrogenation of an acylbenzene to yield ...
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an alkylbenzene
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The Wolff-Kishner reduction is more general and more useful than catalytic hydrogenation because ?
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it works well with both alkyl and aryl ketones
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