acetoacetic ester synthesis (reactant)
acetoacetic ester
acetoacetic ester
MeC-CO-CH2-CO-OEt
acetoacetic ester synthesis (types)
adds 1 or 2 R groups
acetoacetic ester synthesis (1R - reagent)
1. NaOEt, EtOH
2. RX
3. Hydrolyze/Decarboxylyze
acetoacetic ester synthesis (2R - reagent)
1. NaOEt, EtOH
2. RX
3. KOt-Bu, EtOH
4. RX
5. Hydrolyze/Decarboxylyze
acetoacetic ester synthesis (1R - product)
replaces ester (CO2Et) with R
acetoacetic ester synthesis (2R - product)
replaces ester (CO2Et) and an alpha H with 2 R groups
Hydrolyze/Decarboxylyze (reagent steps)
Saponify Acidify Carboxylic acid Heat Decarboxylate (SAC'D)
Hydrolyze/Decarboxylyze (reagents)
1. -OH, H2O
2. H3O+
3. Heat
acetoacetic ester synthesis (1R - steps)
1. alpha C deprotonation by -OEt
2. -C attacks R of RX
3. hydrolyze: Et of ester replaced with H
4. heat: CO2 deleted
acetoacetic ester synthesis (2R - steps)
1. alpha C deprotonation by -OEt
2. -C attacks R of RX
3. alpha C deprotonation by -OEt
4. -C attacks R of RX
5. hydrolyze: Et of ester replaced with H
6. heat: CO2 deleted