Chapter 7: Aldehydes and Ketones II - Enolates Flashcards
enol-
Presence of carbon-carbon double bonds and an alcohol.
Due to the acidity of alpha hydrogens in aldehyde and ketones, they can exist in solution as a mixture of two isomers.
enol and keto
alpha-carbon
adjacent to the carbonyl carbon
alpha-hydrogen
hydrogen attached to the alpha-carbons
the acidity of alpha-hydrogen
is augumented by resonance stabilization of the conjugate base
carbanion
molecule with a negatively cahrged carbon atom
alpha-hydrogen in ketones are ____ than alpha-hydogen in aldehydes
less
ketones are ____ likely to react with nucleophiles than aldehydes
less
enolization can also be called:
tautomerization
alpha-racemization
Any aldehyde or ketone with chiral alpha carbon will rapidly become a racemic mixture as the keto and enol forms interconvert, a phenomenon known as alpha racemization.
kinetic enolate
Any aldehyde or ketone with chiral alpha carbon will rapidly become a racemic mixture as the keto and enol forms interconvert, a phenomenon known as alpha racemization.
Thermodynamically controlled
product is formed with the double bond being formed with the more substituted alpha carbon. The thermodynamic product is favored with higher temperatures, slow, reversible reactions.
enamines
are tautomers of imines
tautomerization
Movement of a hydrogen and a double bond.
Which is more thermodynamically Favored? Enamine or imine
imine
adol condensation
Aldehyde and ketone act both as an electrophile and a nucleophile, and the end result is the formation of a carbon carbon bond.
aldol
contain ALDehyde and alcohOL
condensation reaction can also be a ____reaction if the molecule lost is water
dehydration
retro-aldol reaction
Happens if aqueous base is added and heat is applied. It is when a breaking bond between the alpha and beta carbons of a carbonyl.
