CHM2120 final exam reagents

Halogenation

AcOH (mono-halogenation)

NaOH (poly halogenation)

Alkylation

1) base (LDA, -78 celcius, THF) -kinetic enolate

2) RCH2-Br

Aldol

1) LDA, -78 celcius, THF -kinetic enolate

2) electrophile (ketone or aldehyde)

3) NH4Cl, H2O

Aldol condensation

NaOH, EtOH, heat

or

H3O+, heat

Claisen condensation (Deickmann condensation is the intramolecular Claisen condensation)

1) NaOR’, R’OH

2) NH4Cl, H2O

Decarboxylation

1) KOH (saponification)

2) HCl, heat (removal of CO2)

Ozonolysis

1) O3, CH2Cl2, -78

2) (CH3)2 S, or PH3P or Zn/HOAc

EAS: Friedel-Crafts acylation

in the presence of lewis acid: AlCl3 or FeBr3

Markovnikov (tautomerization acidic conditions) electrophile needed

Hg(OAc)2, H2O

H2SO4

Anti-Markovnikov (tautomerization basic conditions) electrophile needed

1) BHR2, THF

2) H2O2, NaOH