acetals, imine, enamine, protective groups, etc. (ch 19) Flashcards
H3O+
acetal, imine, or enamine –> carbonyl group
[H+] 2 ROH
aldehyde/ketons –> acetal. can be used to protect aldehydes/ketons
[H+] HOCH2CH2OH
aldehyde/ketone –> cyclic acetal. can be used as protective group.
[H+] HSCH2,CH2,SH
aldehyde/ketone –> cyclic thioacetal
Raney nickel
thioacetal —> alkane
[H+] RNH2
aldehyde/ketone –> imine
[H+] R2NH
aldehyde/ketone –> enamine
[H+] NH2OH
aldehyde/ketone –> oxime
[H+] NH2NH2
aldehyde/ketone –> hydrazone
NaOH, H2O, heat
hydrazone –> alkane
- LiAlH4 2. H3O+
aldehyde/ketone –> alcohol
- RMgBr 2. H3O+
forms alcohol w new C-C bond
HCN, KCN
aldehyde/ketone –> cyanohydrin
Wittig reaction (RCHPPh3)
forms alkene w new C=C bond in loction of former carbonyl group
RCO3H
ketone –> ester
TMSCl, Et3N
protects alochol
TBAF
deprotects alochol