"Master Organic Chemistry"
Summary Sheet - The Oxidation Ladder
Note - this sheet is not meant to be comprehensive. Your course
may provide additional material, or may not cover some of the
reactions shown here. Your course instructor is the final authority.
masterorganicchemistry.com
June 2011. Version 1.0
Oxidation state of carbon
+4
Notes: to keep things relatively simple, several common functional groups (amines,
epoxides, ethers, and many more) have been omitted.
CO2
Indicates oxidations
Indicates reductions
Neither oxidations nor reductions
All alkyl halides are drawn as chlorides ("Cl"). For Br and I, the corresponding
reagent containing those atoms should be employed.
Carbon dioxide
Oxidation here is defined as: loss of a C–H bond or gain of a C–O bond (or equivalent)
Reduction here is defined as: gain of a C–H bond or loss of a C–O bond (or equivalent)
H2O, acid
ROH, acid
O
LiAlH4
+2
R
HO
Carboxylic acid
O
SOCl2
H2O or NaOH
NH3 or other
amine
R
Cl
Acid halide
O
P2O5
R
H2N
N
H2O, acid
Amide
O
C
R
RO
Ester
Nitrile
R
H2O, acid
R
E
D
U
C
T
I
O
N
O
X
I
D
A
T
I
O
N
amine, DCC
NH3 or other amine
mCPBA
O3, H2O
H2CrO4
or H2O2
H2CrO4
or
KMnO4
H2O, H2SO4 or HgSO4, H2O, H2SO4
BH3, H2O2
O
0
NaNH2
Cl
R
NaNH2
R
H
Aldehyde
NaBH4
or
PCC
LiAlH4
R
Alkyne
Cl
Dihalide
(Vicinal)
HCl
R
Ketone
Dihalide
(Geminal)
O3, Zn (or DMS)
H2SO4, heat
NaOH (SN2)
-2
Alcohol
(Primary)
Cl
PCl3 or SOCl2
R
R
base (e.g. NaOEt)
Alkene
Alkyl halide
(Primary)
Pd/C
H2
NaOH
(SN2)
Cl
HCl
base (e.g. NaOEt)
Mg, then acid
PCC
or
H2CrO4
R
Alkyl halide
(Secondary)
HCl
OH
R
Alcohol
(Secondary)
OH
R
Alcohol
(Tertiary)
Mg, then acid
Cl2,
light
–4
NaBH4
or
LiAlH4
H2O, H2SO4 or Hg(OAc)2, H2O, then NaBH4
BH3, H2O2
R
RMgCl
or
RLi
O
R
H2,
Lindlar's
catalyst
Cl2
O3, Zn (or DMS)
Cl Cl
H2SO4, heat
HO
RMgCl
or
RLi
DIBAL
Cl2,
light
R
R
Alkanes
Omissions, Mistakes, Suggestions?
james@writechem.com
This sheet copyright 2011, James A. Ashenhurst
masterorganicchemistry.com