Together with the summary of Simple Functional Group Interconversions and basic carboncarbon bond forming reactions summarized elsewhere, this summary represents all possible
reactions that could be encountered on a CHM 234 Final exam.
Generating a summary such as this is difficult, since all aspects of the reactions can't be simply
summarize, such as stereochemistry, for example. In addition, part of the issue of reactions is
recognizing how to use them outside of the context of this summary, and so please use this
summary with care and understand that there is more to doing well on the final exam than
knowing the reactions here.
Br
H2
H
Pd/C (or Pt or Raney Ni)
H
CN
Na+ –CN
Na2Cr2O7
O
H
oxidation of ALDEHYDE to acid
OH
SOCl2
alcohol to chloride
Cl
PBr3
OH
SN2 reaction
you will generally need to
WORK OUT the reagents for
SN2 reactions
O
H2SO4 / H2O
OH
O
reduction of alkenes to alkene
alcohol to bromide
Br
O
Na+ –H
O– +Na
OH
NaOH can NOT be used here
Br
O– +Na
O
O
Williamson ether synthesis
HO
CH3OH
must be an organic acid, HCl, TsOH etc.
H+ (cat.)
OCH3
OH
O
CH3OH
NaOCH3
CH3O
Ph
Br
CH3OH
W
+
Δ
W
+
H3CO
OCH3
+
heat
W
Ph
basic conditions gives
opposite regiochemistry
and other reactions of
conjugated systems that
have kinetic and
thermodynamic products
Diels-Alder reaction
W
Δ
Δ
and other pericyclic
cycloaddition reactions solved
using FMO or aromatic
transition state theory
electrocyclic ring opening/closing
solved using FMO or aromatic
transition state theory
O
Zn (Hg)
Clemmenson reduction
HCl /H2O
Et
Me
1. KMnO4 / –OH/boil
2. H3
t-Bu
NO2
O+
HO2C
CO2H
t-Bu
NH2
H2/Pd/C
Br
Br2
FeBr3
Cl2
SO3
SO3H
electrophilic aromatic substitution
sulfonation
NO2
electrophilic aromatic substitution
nitration
H2SO4
O
/AlCl3
Cl
electrophilic aromatic substitution
bromination
electrophilic aromatic substitution
chlorination
H2SO4
HNO3
reduction of nitro to amine, amine
synthesis
Cl
AlCl3
O
alkyl oxidation
C
Friedel-Crafts acylation
H
C O
CO/HCl/AlCl3
O
HO OH
O
O
Gatterman Koch reaction
acetal formation
HCl (cat.)
O
O
O
H3O+
H2N
C
O
O
Ph
C
CH3
O
acetal hydrolysis
Ph
Ph
formation of imine
N
H+ (cat.)
N
H
H+ (cat.)
N2H4
KOH, heat
N
Ph
formation of enamine
CH2
Wolf Kischner reduction
O
O
1. LDA
2.
O
Br
1.
N
2. H3
alpha-alkylation via
enolate using LDA
Br
Stork enamine
alkylation
O+
TsOH or Na+–OH
O
O
Aldol condensation, many variants
heat
O
Ph
1. Na+ –OR
O
+
OR
2. H3O+
O
O
Claisen condensation, many variants
Ph
CO2H
Excess SOCl2
COCl
CO2H
1. LiAlH4
OH
acid to acid chloride
reduction of carboxylic acid to alcohol
2. H3O+
O
O
Cl
O
O
O
HO
anhydride synthesis
O
O
EtOH
OEt
Cl
O
O
NH3
Br
O
Na+ –CN
C N
H2O
O
Cl
O
H2O
O
O
N C
–OH
acid chloride hydrolysis
no catalyst required
–OH
O
anhydride hydrolysis
no catalyst required
OH
OH O
O
or H3O+/heat (boil)
HO
1. (Excess) LiAlH4
Cl
O
2
or H3O+/heat
NH2
O
nitrile synthesis via SN2
OH
O
O
amide synthesis
NH2
Cl
O
ester synthesis
1. (Excess) LiAlH4
2. H3
O+
ester hydrolysis catalyst required
O
OH
OH
2. H3O+
O
OH
OH OH
amide and nitrile hydrolysis
forcing conditions required
acid chloride reduction
ester reduction
H
N
1. (Excess) LiAlH4
O
2. H3
C
Br
amide reduction to form an amine
O+
1. (Excess) LiAlH4
N
H
N
2. H3O+
1. NaN3
2. LiAlH4
3. H3
NH2
2. H2/Pd/C
CH3NH2/H+ (cat.)
O
azide reduction to form an amine
O+
1. NH3/H+ (cat.)
O
nitrile reduction to form an amine
NH2
NaBH3CN
1°
NH2
NH
2°
INDIRECT
reductive amination
DIRECT
reductive amination