The Oxidation Ladder - Elem Organic Chem PDF

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Elem Organic Chem...

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"Master Organic Chemistry"

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.

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Oxidation state of carbon

Carbon dioxide

• 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.

(from combustion!)

• 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)

CO2

Indicates oxidations Indicates reductions Functional group transformations

H 2O, acid

LiAlH 4

ROH, acid O LiAlH 4

R

HO

Carboxylic acid

O

SOCl2

R

Cl

H 2O or NaOH

NH 3 or other amine

Acid halide

O

P 2O 5 R

H 2N

N

H 2O, acid

Amide

O C

R

RO Ester

Nitrile

R

H 2O, acid

R E D U C T I O N

O X I D A T I O N

amine, DCC

NH 3 or other amine m-CPBA

O 3, H 2O H 2CrO4 or H 2O 2

H 2CrO4 or KMnO 4

H 2O, H 2SO4 or HgSO4, H 2O, H 2SO4

BH 3, H 2O 2 O

NaNH2

NaBH 4 or LiAlH 4

Cl Dihalide (Vicinal)

H 2SO4, heat

H 2SO4, heat

Alcohol (Primary)

Cl PCl 3 or SOCl2

R

NaBH 4 or LiAlH 4

PCC or H 2CrO4

H 2O, H 2SO4 or Hg(OAc) 2, H 2O, then NaBH4

BH 3, H 2O 2

R

RMgCl or RLi

O R Ketone

O 3, Zn (or DMS)

NaOH (SN2) HO

Cl

Dihalide (Geminal)

H 2, Lindlar's catalyst

Cl2

O 3, Zn (or DMS)

Cl

R

HCl

R Alkyne

R

Aldehyde

PCC

NaNH2

Cl

R

H

RMgCl or RLi

DIBAL

R Alkene

Alkyl halide (Primary)

base (e.g. NaOEt)

Pd/C H2

Mg, then acid

NaOH (SN2)

Cl

HCl

base (e.g. NaOEt)

R Alkyl halide (Secondary)

HCl

OH R Alcohol (Secondary)

OH R Alcohol (Tertiary)

Mg, then acid Cl2, light

Cl2, light R

R

Alkanes Omissions, Mistakes, Suggestions? [email protected] This sheet copyright 2019, James A. Ashenhurst masterorganicchemistry.com...