Ch_322b_19.09

Ch_322b_19.09 - Chapter 19.9 lecture note

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Synthesis and Reaction of Enamines: Alkylation and Acylation Aldehydes and ketones with enolizable H may be alkylated and acylated by way of their enamine derivatives . Imines Primary amines react with aldehydes and ketones to form imines : If there is an enolizable H in R or R', an equilibrium exists: However, the imine isomer is more stable than the enamine just as the ketone isomer is more stable than the enol. R R' + R''-NH 2 1 o -amine R-C-NHR'' OH R' C=O R R' C=NR'' + H 2 O imine nucleophilic addition dehydration C C H 2 R' R N R'' = imine C N R'' H R CHR' enamine tautomerization
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Secondary Amines Give Only Enamines When a 2 o -amine reacts with an aldehyde or ketone with enolizable H: dehydration in the addition product can only yield an enamine . Enamine formation is catalyzed by acid and promoted by removing the water as it is formed. C R C H 2 R' O = + NH R'' R''' 2 o -amine R-C-OH N R'' R''' C H 2 R' nucleophilic addition R-C-OH N R'' R''' C H 2 R' C=CHR' R N R'' R''' enamine + H 2 O
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This note was uploaded on 10/20/2009 for the course CHEM 322BL at USC.

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Ch_322b_19.09 - Chapter 19.9 lecture note

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