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