Alkene Addition Overview

What groups are added across the π bond in Hydrohalogenation (Polar)?

-H
-X

What groups are added across the π bond in Hydrohalogenation (Radical)?

-H

-Br

What groups are added across the π bond in Acid-Catalyzed Hydration?

-H

-OH

What groups are added across the π bond in Oxymercuration-Demercuration?

-H

-OH

What groups are added across the π bond in Hydroboration-Oxidation?

-H

-OH

What groups are added across the π bond in Catalytic Hydrogenation?

-H

-H

What groups are added across the π bond in Halogenation?

-X

-X

What groups are added across the π bond in Halohydrin Formation?

-X

-OH

What groups are added across the π bond in Anti-Dihydroxylation?

-OH

-OH

What groups are added across the π bond in Syn-Dihydroxylation?

-OH

-OH

What groups are added across the π bond in Oxidative-Cleavage?

n/a

What are the reagents for Hydrohalogenation (Polar)?

HX/insert solvent (no H2O or ROH)

What are the reagents for Hydrohalogenation (Radical)?

HBr/ROOR

What are the reagents for Acid-Catalyzed Hydration?

dilute H2SO4

What are the reagents for Oxymercuration-Demercuration?

1.Hg(OAc)2, H2O, or ROH

2.NaBH4

What are the reagents for Hydroboration-Oxidation?

1.BH3, THF

2.H2O2, NaOH

What are the reagents for Catalytic Hydrogenation?

H2/Pt or H2/Wilkenson’s Cat.

What are the reagents for Halogenation?

X2/Chlorinated solvent (no H2O or ROH)

What are the reagents for Halohydrin Formation?

X2/H2O or ROH

What are the reagents for Anti-Dihydroxylation?

1.RCO3H

2.H3O

What are the reagents for Syn-Dihydroxylation?

OsO4/NMO

What are the reagents for Oxidative Cleavage?

1.O3

2.DMS

What is the stereochemistry (anti/syn/neither) for Hydrohalogenation (Polar)?

neither

What is the stereochemistry (anti/syn/neither) for Hydrohalogenation (Radical)?

neither

What is the stereochemistry (anti/syn/neither) for Acid-Catalyzed Hydration?

neither

What is the stereochemistry (anti/syn/neither) for Oxymercuration-Demercuration?

anti

What is the stereochemistry (anti/syn/neither) for Hydroboration-Oxidation?

syn

What is the stereochemistry (anti/syn/neither) for Catalytic-Hydrogenation?

syn

What is the stereochemistry (anti/syn/neither) for Halogenation?

anti

What is the stereochemistry (anti/syn/neither) for Halohydrin Formation?

anti

What is the stereochemistry (anti/syn/neither) for Anti Dihydroxylation?

anti

What is the stereochemistry (anti/syn/neither) for Syn Dihydroxylation?

syn

What is the stereochemistry (anti/syn/neither) for Oxidative Cleavage?

neither

What regiochemistry (Markovnikov/Anti-Markovnikov) for Hydrohalogenation (Polar)?

Markovnikov

What regiochemistry (Markovnikov/Anti-Markovnikov) for Hydrohalogenation (Radical)?

Anti-Markovnikov

What regiochemistry (Markovnikov/Anti-Markovnikov) for Acid-Catalyzed Hydration?

Markovnikov

What regiochemistry (Markovnikov/Anti-Markovnikov) for Oxymercuration-Demercuration?

Markovnikov

What regiochemistry (Markovnikov/Anti-Markovnikov) for Hydroboration-Oxidation?

Anti-Markovnikov

What regiochemistry (Markovnikov/Anti-Markovnikov) for Catalytic Hydrogenation?

n/a

What regiochemistry (Markovnikov/Anti-Markovnikov) for Halogenation?

n/a

What regiochemistry (Markovnikov/Anti-Markovnikov) for Halohydrin Formation?

n/a

What regiochemistry (Markovnikov/Anti-Markovnikov) for Anti Dihydroxylation?

n/a

What regiochemistry (Markovnikov/Anti-Markovnikov) for Syn Dihydroxylation?

n/a

What regiochemistry (Markovnikov/Anti-Markovnikov) for Oxidative Cleavage?

n/a

Are there carbocation rearrangements for Hydrohalogenation (Polar)?

yes

Are there carbocation rearrangements for Hydrohalogenation (Radical)?

no

Are there carbocation rearrangements for Acid-Cataylzed Hydration?

yes

Are there carbocation rearrangements for Oxymercuration-Demercuration?

no

Are there carbocation rearrangements for Hydroboration-Oxidation?

no

Are there carbocation rearrangements for Catalytic Hydrogenation?

no

Are there carbocation rearrangements for Halogenation?

no

Are there carbocation rearrangements for Halohydrin Formation?

no

Are there carbocation rearrangements for Anti Dihydroxylation?

no

Are there carbocation rearrangements for Syn Dihydroxylation?

no

Are there carbocation rearrangements for Oxidative Cleavage?

no