Reactants

HX

HBr/ROOR

-Regios, Stereo, intermediate, Rearrange

Hydrohalogenation

-HX-Mark, none, carbocat, possible

-HBr/ROOR, Anti Mark

-none

H3O^+ (dil. H2SO4)

1.) Hg(OAc)2, H2O

2.) NaBH4

1.) BH3 * THF

2.) H2O2, NaOH

Regios, Stereo, intermediate, Rearrange

Hydration

(adds H & OH)

-Mark, none, carbocat, possible

-Mark, anti, merconium, no

-AntiMark, syn triakyl borane, no

-ROH, H^+ (usually H2SO4)

1.) Hg(OAc)2, ROH

2.)NaBH4

Regios, Stereo, intermediate, Rearrange

Alcohol Addition

(adds H and OR)

-Mark, none, carbocat, possible

-Mark, anti, mercurinium ion, no

H2/Cat (Pt, Pd, Ni)

Catalytic Hydrogenation

(add H and H)

syn addition, no rearrangement

(Br2 or Cl2) / (CCl4, CH2Cl2)

Halogenation

(add X and X)

-anti, halnoium int., no re

-X2/ H2O

-X2/ ROH

Regios, Stereo, intermediate, Rearrange

Halohydrin Formation

(add X and OH/OR)

-mark, anti, halonium, no

-mark, anti, halonium, no

1.) RCO3H (usually MCPBA)

2.) H3O+

1.) OsO4

2.)NaHSO3 or Na2SO3

-KMnO4/NaOH

Dihydroxylation

(add OH and OH)

-anti, epoxide, no

-syn, cylic osmate ester, no

-syn, cyclic manganate ester, no

Hydrohalogenation (HCl, HBr, HI)

Hydroboration with Peroxide

Halogenation (Br2 or Cl2)

Acid-Catalyzed Hydration of a Terminal Alkyne

Hydroboration-Oxidation of a Terminal Alkyne

Hydration of an Internal Alkyne

Ozonolysis of an Internal Alkyne

Ozonolysis of a Terminal Alkyne

Alkylation of Acetylide Ions

Free Radical Bromination (High selectivity)

Free Radical Chlorination (low selectivity)

Allylic/ Benzylic Bromination

Acid Catalyzed cleavage of Ethers

Epoxidation with a Peroxyacid

Ozonolysis Under Reducing Conditions

Hydration of a Terminal Alkyne (Mark)

Hydration of a Terminal Alkyne (Anti-Mark)

Hydration of an Internal Alkyne

Sodium Borohydride

Hydride Reduction

Ozonolysis of Alkenes under Oxidizing of Alkynes

Ozonolysis

Reduction

Hydride Reduction

Hoffman Rearrangement

GrignardsAddition