Alkene Addition Diagrams

1. BH₃

2. H₂O₂, OH-

Hydroboration

1. Hg(OAc)₂ , H₂O
2. NaBH₄

(OAc = O₂CCH₃)

Oxymercuration-Demurcuration

1. Hg(OAc)₂ , ROH
2. NaBH₄

(OAc = O₂CCH₃)

Alkoxymercuration-Demurcuration

H₃O+

Acid-Catalyzed Hydration

ROH, H+

or
ROH, H₃PO₄

or

ROH, H₂SO₄

Acid-catalyzed addition of an alcohol

HCl

Hydrohalogenation

HBr

Hydrohalogenation

HI

Hydrohalogenation

HBr, ROOR

Radical Addition of HBr

Br₂ / CCl₄

Halogenation (bromination)

Cl₂ / CCl₄

Halogenation (chlorination)

Br₂ , H₂O

Halohydrin Formation

Cl₂ , H₂O

Halohydrin Formation

1. mCPBA

2. H₃O+
or

1. RCO₃H

2. H₃O+

Anti-Dihydroxylation

1. OsO₄

2. H₂O₂
or
OsO₄ , NMO
or

KMnO₄ (dilute, cold)

Syn-Dihydroxylation

H₂ , Pd/C

or

H₂ , Pt or PtO₂

_or

H₂ , Ni

Hydrogenation (Catalytic Reduction)

mCPBA

or

RCO₃H

Epoxidation

1. O₃

2. (CH₃)₂S
or

1. O₃

2. Zn/H+

Reductive Ozonolysis

1. O₃

2. H₂O₂

Oxidative Ozonolysis

KMnO₄ , (hot, conc)

Oxidative Cleavage

CH₂I₂ , Zn(Cu)

Cyclopropanation (Simmons–Smith Reaction)

CHCl₃ , OH-

Cyclopropanation (Carbene Addition)