"Master Organic Chemistry"

Summary Sheet - The Oxidation Ladder

Oxidation state of carbon

masterorganicchemistry.com June 2011. Version 1.0

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.

+4

Indicates oxidations Indicates reductions Neither oxidations nor reductions

CO2 Carbon dioxide

Notes: to keep things relatively simple, several common functional groups (amines, epoxides, ethers, and many more) have been omitted. All alkyl halides are drawn as chlorides ("Cl"). For Br and I, the corresponding reagent containing those atoms should be employed. Oxidation here is defined as: loss of a CH bond or gain of a CO bond (or equivalent) Reduction here is defined as: gain of a CH bond or loss of a CO bond (or equivalent)

H2O, acid ROH, acid O O Cl R NH3 or other amine O H2N Amide H2O, acid R P2O5 H2O, acid O C R RO Ester R

+2

LiAlH4

HO

SOCl2 H2O or NaOH

Carboxylic acid

Acid halide

Nitrile

R E D U C T I O N 0

O X I D A T I O N

amine, DCC O3, H2O H2CrO4 or H2O2

NH3 or other amine mCPBA RMgCl or RLi

H2CrO4 or KMnO4

DIBAL

BH3, H2O2 O H Aldehyde R Cl R Cl Dihalide (Vicinal) Cl2

H2O, H2SO4 or HgSO4, H2O, H2SO4 NaNH2 NaNH2 R Alkyne H2, Lindlar's catalyst HCl Cl Cl R Dihalide (Geminal) R Ketone O RMgCl or RLi

NaBH4 or PCC LiAlH4

O3, Zn (or DMS) H2SO4, heat BH3, H2O2 NaOH (SN2)

O3, Zn (or DMS) H2SO4, heat H2O, H2SO4 or Hg(OAc)2, H2O, then NaBH4 Cl R Alkyl halide (Secondary) NaOH (SN2) HCl

NaBH4 or LiAlH4

PCC or H2CrO4

HO

-2

Cl PCl3 or SOCl2

base (e.g. NaOEt)

HCl R Alkene base (e.g. NaOEt)

OH R Alcohol (Secondary)

OH R Alcohol (Tertiary)

Alcohol (Primary)

Alkyl halide (Primary)

Mg, then acid

Pd/C H2

Mg, then acid

Cl2, light

Cl2, light R Alkanes Omissions, Mistakes, Suggestions? james@writechem.com This sheet copyright 2011, James A. Ashenhurst masterorganicchemistry.com R