Addition Reactions of Alkenes (Chem 2311)

Name: Hydrohalogenation

Regiochem: Markovnikov

Stereochem: n/a

What reagent(s) is/are needed to complete this reaction?

HX (where X is a halogen)

Name: Anti-M. Addition of HBr

Anti-Markovnikov

Stereochem: n/a

What reagent(s) is/are needed for this reaction?

HBr, ROOR

Name: Acid-Catalyzed Hydration

Regiochem: Markovnikov

Stereochem: n/a

What reagent(s) is/are needed for this reaction?

H3O+ (usually via dilute H2SO4)

Name: Oxymercuration Demercuration

Regiochem: Markovnikov (prevents rearrangement)

Stereochem: n/a

What reagent(s) is/are needed for this reaction?

1) Hg(OAc)2, H2O

2) NaBH4

Name: Hydroboration-Oxidation

Regiochem: anti-Markovnikov

Stereochem: Syn addition (both OH and H wedges/both dashes)

What reagent(s) is/are needed for this reaction to occur?

1) BH3 . THF

2) H2O2, NaOH

Name: Catalytic Hydrogenation

Regiochem: n/a

Stereochem: syn

What reagent(s) is/are needed for this reaction?

H2, Pt

Name: Bromination/Chlorination

Regiochem: n/a

Stereochem: anti-addition (one wedge, one dash or v.v.)

What reagent(s) is/are needed for this reaction? (Can also include Cl instead of Br)

Br2/Cl2

Name: Halohydrin Formation

Regiochem: OH is Markovnikov, halogen is anti-M.

Stereochem: Anti (one wedge one dash and v.v.)

What reagent(s) is/are needed for this reaction?

Br2, H2O

Name: Syn Dihydroxylation

Regiochem: n/a

Stereochem: syn (both wedge or both dash)

What reagent(s) is/are needed for this reaction (two possible answers)

Option 1: KMnO4, NaOH (cold)

Option 2: 1) OsO4 2) NMO

Name: Anti Dihydroxylation

Regiochem: n/a

Stereochem: anti (one wedge other dash or v.v.)

What reagent(s) is/are needed for this reaction?

1) RCO3H

2) H3O+

Name: Ozonolysis

Regiochem: n/a

Stereochem: n/a

What reagent(s) is/are needed for this reaction?

1) O3

2) DMS

Which addition reactions include a three-ring intermediate?

1. Halogenation (Br2/Cl2)

2. Halohydrin Formation (Br2, H2O)

3. Anti Dihydroxylation (1. RCO3H 2. H3O+) —→ epoxide is intermediate

4. Oxymercuration-Demercuration (1. Hg(OAc)2, H2O 2. NaBH4)