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Unformatted text preview: 2 NR) with the acids anion This yields the carbinal amine! 4. Protonate the OH oxygen with acid to make water, a good LG 5. Attack H (part of a C-H adjacent to the C-N bond) with the acids anion E1 results in a double bond formation This yields the enamine! Wolff-Kishner rxn: (Aldehyde/Ketone Alkane) 1. HNNH 2 addn to the carbonyl carbon; H + addn to the carbonyl oxygen to makeOH 2. Attack H (on HNNH 2 ) with OH; push the electrons; C=N double bond forms; -OH leaves 3. A second OH comes in; attacks H (on NNH 2 ); push the electrons to make the carbanion 4. Carbanion steals an H + from H 2 O to make a neutral molecule 5. A third OH comes in; attacks H (on NNH); push the electrons to make N N leave; result is a carbanion 6. Carbanion steals an H + from H 2 O This yields the alkane!...
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- Spring '08