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8 Cards in this Set

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What is a useful method for turning an aldehyde or ketone into an alkene, R2C=0 ~~> R2CH2
Wolff-Kishner Rxn
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..
to take place near room temp.
The Wolff-Kishner Rxn involves formation of a hydrazone intermediate, R2C=NNH2, followed by ...
base-catalyzed double-bond migration, loss of N2 gas, and protonation to give the alkane product
The double-bond migration of a Wolff-Kishner Rxn takes place when ...
the base removes a of the weakly acidic NH protons to generate a hydrozone anion
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
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
The Wolff-Kishner reduction accomplishes the same overall transformation as the catalytic hydrogenation of an acylbenzene to yield ...
an alkylbenzene
The Wolff-Kishner reduction is more general and more useful than catalytic hydrogenation because ?
it works well with both alkyl and aryl ketones