Alkene Addition Reactions

Question 1

Hydration (acid catalyzed)

Answer 1

Reagents: H2SO4 / H2O 
Groups Added: OH & H; 
Config: both syn & anti; 
Markovnikov 
Stepwise

Question 2

Oxymercuration-Demercuration

Answer 2

Reagents: 1. Hg(OAc)2, H2O / 2. NaBH4; 
Groups Added: OH & H; 
Config: both syn & anti; 
Markovnikov; 
Concerted

Question 3

Hydroboration-Oxidation

Answer 3

Reagents: 1. BH3, THF / 2. H2O2, -OH; 
Groups Added: OH & H; 
Config: syn; 
Anti-Markovnikov; 
Concerted

Question 4

Syn-Dihydroxilation

Answer 4

Reagents: OsO4 / NaHSO3; 
Groups Added: OH & OH; 
Config: syn; 
Markovnikov N/A; 
Concerted

Question 5

Anti-Dihydroxilation

Answer 5

Reagents: MCPBA / H2O, H+; 
Groups Added: OH & OH; 
Config: anti; 
Markovnikov N/A; 
Concerted

Question 6

Halohydrin

Answer 6

Reagents: X2 / H2O; 
Groups Added: X & OH; 
Config: anti; 
Markovnikov (OH); 
Stepwise (carbocation rearrangement)

Question 7

Halogenation

Answer 7

Reagents: X2; 
Groups Added: X & X; 
Config: anti; 
Markovnikov & Anti-Markovnikov; 
Concerted

Question 8

Hydrohalogenation

Answer 8

Reagents: H--X; 
Groups Added: H & Br; 
Config: anti & syn; 
Markovnikov; 
Stepwise (carbocation rearrangement)

Question 9

Catalytic Hydrogenation

Answer 9

Reagents: H2, Pd or Pt or Ni; 
Groups Added: H & H; 
Config: syn; 
Markovnikov N/A; 
Concerted/Stepwise N/A

Question 10

Ozonolysis

Answer 10

Reagents: O3 / DMS; 
Groups Added: =O & =O; 
Config: sp2; 
Markovnikov N/A; 
Concerted/Stepwise N/A

Question 11

HBr + ROOR

Answer 11

Reagents: HBr / ROOR (peroxide); 
Groups Added: H & Br; 
Config: anti; 
Anti-Markovnikov; 
Stepwise (carbocation rearrangement)