Synthetic Transformations

Markov Addition of H and OH

1) Hg(OAC)2, H2O/THF

2) NaBH4

Markov Addition of H and OR

1) Hg(OAC)2, HOR/THF

2) NaBH4

Anti-Markov Addition of H and OH

1) BH3/THF

2) H2O2,NaOH/H2O

Anti-Markov Addition of H and Br

HBR, peroxides (ROOR)/ heat or light

Markov Addition of H and X

HX/cold,dark,no peroxides

Addition of Br2 to Alkene

Br2

Oxidation of Alkene to Epoxide

MCPBA

Anti-Markov Epoxide Ring Opening (Basic Conditions)

1) Strong base (KOH, RO-, R2N-)

2) Dilute Acid for H added to O or Primary Alkyl Halide (R’X) for primary alkyl add

Markov Epoxide Ring Opening (Acidic Conditions)

H+/HOR gives trans

Markov Addition of Br and OR to Alkene

Br2, HOR

Cyclopropane Ring from Alkene 1

CHCl3, KOH

Cyclopropane Ring from Alkene 2

CH2I2, Zn(Cu)

Hydroboration-Oxidation

1) BH3/THF

2) H2O2,NaOH/H2O

H2, Pt or Pd

1. H2/Pt (breaks ALL pi bonds)

2. H2/Lindlar Catalyst (gives cis and breaks 1 pi bond)

3. NaNH3 (gives trans and breaks 1 pi bond)

PCC

KMnO4

or

Na2Cr2O7/acid/water

or

CrO3/acid/water

KMnO4

or

Na2Cr2O7/acid/water

or

CrO3/acid/water

1) OsO4

2) H2O2 or NaHSO3

1) Ozone

2) Zn, acetic acid

1) KMnO4(hot)

2) H3O+/ H2O

1) HX/ dark,cold,no peroxides

2) more HX/ dark,cold, no peroxides

1) X2

2) more X2

H2O, H2SO4, HgSO4

1) BH3, THF

2) H2O2, NaOH, H2O

NaNH2

H2O, H2SO4

Anti-markov bc radical Cl2, light (hv)

Anti-markov bc radical Br2, light (hv)