"Master Organic Chemistry" Note - this sheet is not meant to be comprehensive.

Your course
Summary Sheet - The Oxidation Ladder masterorganicchemistry.com may provide additional material, or may not cover some of the
reactions shown here. Your course instructor is the final authority.
June 2011. Version 1.0

Oxidation state of carbon

Notes: to keep things relatively simple, several common functional groups (amines,
Indicates oxidations CO2 epoxides, ethers, and many more) have been omitted.
+4 Indicates reductions All alkyl halides are drawn as chlorides ("Cl"). For Br and I, the corresponding
reagent containing those atoms should be employed.
Carbon dioxide
Neither oxidations nor reductions
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 SOCl2 O NH3 or other O P2O5 O

N
LiAlH4
+2 HO
R
Cl
R amine
H2N
R
H2O, acid
C R
RO
R
H2O or NaOH
Carboxylic acid Acid halide Amide Nitrile Ester

H2O, acid

R O amine, DCC NH3 or other amine

E X mCPBA
D I O3, H2O
U D H2CrO4 RMgCl
C A H2CrO4
or H2O2
DIBAL
or
T T or
RLi

I I KMnO4
O O BH3, H2O2 H2O, H2SO4 or HgSO4, H2O, H2SO4
N N RMgCl
O NaNH2 Cl Cl O or
Cl
NaNH2 RLi
0 H
R R R HCl
R
R
Aldehyde Alkyne Dihalide Ketone
Cl
(Geminal)
Dihalide
(Vicinal) H2,
Lindlar's
NaBH4 PCC
NaBH4 catalyst
Cl2 O3, Zn (or DMS) or or
PCC or O3, Zn (or DMS) LiAlH4 H2CrO4
LiAlH4 H2SO4, heat
H2SO4, heat
BH3, H2O2 H2O, H2SO4 or Hg(OAc)2, H2O, then NaBH4

NaOH (SN2) NaOH

Cl OH OH
HO Cl HCl (SN2)
base (e.g. NaOEt)
R R R R R R
-2 Alcohol
PCl3 or SOCl2
Alkyl halide Alkene base (e.g. NaOEt)
Alkyl halide
HCl
Alcohol Alcohol
(Primary) (Primary) (Secondary) (Secondary) (Tertiary)

Pd/C
H2
Mg, then acid Mg, then acid

Cl2, Cl2,
light light

–4 R R
Alkanes
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This sheet copyright 2011, James A. Ashenhurst
masterorganicchemistry.com