Chapter 7 Flashcards
EWG
oxygen
stabilizes anions
easy to remove when bonds weaken
Why is aldehyde more acidic
has less EDG than ketones
Why are aldehydes more nucleophilic
has less sterics
enol
C=C and alcohol
tautomers
isomers, differ in placement of protons and double bond
keto is favored over Enol
enolate
depronate alpha carbon by base
form carbocation which is a good nu
then carbocation attacks another carbonyl
2 enolates of ketones
kinetic and thermodynamic
kinetic is rapid with double bond as less substituted
thermo is slow and stable with double bond at more sub
when is kinetic product favored
rapid, irreversible, low temp, strong base with sterics
enamine
tautomer of imine
move hydrogen and a double bond
imine vs enamine structure
enamine has c=c
imine has N=c (thermodynamic)
aldol condensation
aldehyde or ketone is electrophile and nucleophile is enol
forms C-C bond between alpha and beta carbon
removes one carbonyl