O-Chem 1 Synthetic Transformations

Addition of H and OH without rearrangement (oxymercuration-demercuration)

1) Hg(OAc)2, H20, THF

2) NaBH4

Addition of H and OR without rearrangement (alkoxymercuration-demercuration)

1) Hg(OAc)2, HOR, THF

2) NaBH4

Anti-Markovnikov Addition of H and OH

1) BH3, THF

2) H2O2, NaOH, water

Anti-Markovnikov Addition of H and BR

1) HBr, peroxides, heat or light

Anti-Markovnikov Addition of H and X (X=Cl, Br, or I)

HX, cold, dark, no peroxides

Addition of Br2 to an Alkene

Br2 (trans only product)

Oxidation of an Alkene to an Epoxide

MCPBA

Anti-Markovnikov Epoxide Ring Opening (basic conditions)

1) strong base (RO-, R2N-, R-, etc)

2) dilute acid (H2SO4)

Markovnikov Epoxide Ring Opening (Acidic Conditions)

H+, HOR

Markovnikov Addition of Br and OR to an Alkene

Br2, HOR

Hydroboration-Oxidation

1) BH3, THF

2) H2O2, NaOH, H2O

Catalytic Hydrogenation

H2, Pt or Pd

Stereoselective Alkyne Reductions (alkyne to single bond with two Hs o each C)

H2, Pt or Pd

Stereoselective Alkyne Reductions (alkyne to double bond with 1 H added to each C - cis)

H2, Ni2B

or

H2, lindlar catalyst

Stereoselective Alkyne Reductions (alkyne to double bond with 1 H added to each C - trans)

oxidation of a primary alcohol to an Aldehyde

PCC

oxidation of secondary alcohol to a Ketone

KMnO4

or

Na2Cr2O7, acid, water

or

CrO3, acid, water

or

PCC

Oxidation of primary alcohol to a carboxylic acid

KMnO4

or

Na2Cr2O7, acid, water

or

CrO3, acid, water

Syn Addition of 2 OH groups

1) OsO4

2) H2O2 or NaHSO3

cleavage of c=c double bond using ozone (ozonalysis)

1) ozone (O3)

2) Zn, acetic acid

cleavage of a c=c double bond using Permanganate (MnO4-)

1) KMnO4 (hot)

2) H3O+, H2O

Markovnikov Addition of H and X

1) HX, dark, cold, no peroxides

2) Excess HX, dark, cold, no peroxides

Markovnikov addition of X2

1) X2

2) excess X2

Markovnikov Addition of H2O to an Alkyne

H2O, H2SO4, HgSO4

Anti-Markovnikov addition of H2O to an Alkyne

1) BH3, THF

2) H2O2, NaOH, H2O

deprotonation of an alkyne

NaNH2

Hydrolysis of a Nitrile

H2O, H2SO4

Halogenation of an Alcohol

HX

or

SOCl2

or

PBr3