Alkene Addition Reactions

hydroboration reagents

1. BH3-THF

2. H2O2, OH-, H2O

1. BH3-THF

2. H2O2, OH-, H2O

what reaction are these reagents from?

hydroboration

hydroboration regiochemistry/stereochemistry

anti-mark, syn

which reaction?

hydroboration

oxymercuration reagents

1. Hg(OAc)2, H2O

2. NaBH4

1. Hg(OAc)2, H2O

2. NaBH4

what reaction are these reagents from?

oxymercuration

oxymercuration regiochemistry/stereochemistry

mark, anti (step 1 only)

which reaction?

oxymercuration

alkoxymercuration reagents

1. Hg(OAc)2, CH3OH

2. NaBH4

1. Hg(OAc)2, CH3OH

2. NaBH4

what reaction are these reagents from?

alkoxymercuration

alkoxymercuration regiochemistry/stereochemistry

mark, anti (step 1 only)

which reaction?

alkoxymercuration

acid-catalyzed hydration reactants

H2O, H2SO4

or H3O+

H2O, H2SO4

what reaction are these reagents from?

acid-catalyzed hydration

H3O+

what reaction are these reagents from?

acid-catalyzed hydration

acid-catalyzed hydration regiochemistry/stereochemistry

mark, unknown stereochemistry

which reaction?

acid-catalyzed hydration

Acid-catalyzed addition of an alcohol reagents

CH3OH, H+

CH3OH, H+
what reaction are these reagents from?

Acid-catalyzed addition of an alcohol

Acid-catalyzed addition of an alcohol regiochemistry/stereochemistry

mark, unknown stereochemistry

which reaction?

Acid-catalyzed addition of an alcohol

alkene addition reactions with Carbocation Rearrangement

Hydrohalogenation
Acid-catalyzed hydration
Acid-catalyzed addition of an alcohol

hydrohalogenation reagents

H-X (X is halogen)

H-X (X is halogen)
what reaction are these reagents from?

hydrohalogenation

hydrohalogenation regiochemistry/stereochemistry

mark, unknown stereochemistry

which reaction?

hydrohalogenation

Radical Addition of HBr reagents

HBr, ROOR

HBr, ROOR

what reaction are these reagents from?

Radical Addition of HBr

Radical Addition of HBr regiochemistry/stereochemistry

anti-mark, unknown stereochemistry

which reaction?

Radical Addition of HBr

halogenation reagents

Br2 or Cl2, CCl4

Br2, CCl4

what reaction are these reagents from?

halogenation (bromination)

halogenation regiochemistry/stereochemistry

N/A, anti

which reaction?

halogenation (bromination)

Cl2, CCl4

what reaction are these reagents from?

halogenation (chlorination)

which reaction?

halogenation (chlorination)

halohydrin formation reagents

Br2, H2O

Br2, H2O

what reaction are these reagents from?

halohydrin formation

halohydrin formation regiochemistry/stereochemistry

mark, anti

which reaction?

halohydrin formation

dihydroxylation reagents

OsO4, H2O2

or

KMnO4 (cold, dilute), OH-

OsO4, H2O2

what reaction are these reagents from?

dihydroxylation

KMnO4 (cold, dilute), OH-

what reaction are these reagents from?

dihydroxylation

dihydroxylation regiochemistry/stereochemistry

N/A, syn

which reaction?

dihydroxylation

hydroxylation reagents

1. mCPBA

2. H3O+

or

1. RCO3H

2. H3O+

1. mCPBA

2. H3O+
what reaction are these reagents from?

hydroxylation

1. RCO3H
2. H3O+
what reaction are these reagents from?

hydroxylation

hydroxylation regiochemistry/stereochemistry

N/A, anti

which reaction?

hydroxylation

epoxidation reagents

RCO3H or MCPBA

RCO3H

what reaction are these reagents from?

epoxidation

MCPBA

what reaction are these reagents from?

epoxidation

epoxidation regiochemistry/stereochemistry

N/A, syn

which reaction?

epoxidation

ozonolysis reagents (reductive workup)

1. O3

2. (CH3)₂S or Zn, H2O

1. O3

2. (CH3)₂S

what reaction are these reagents from?

ozonolysis (reductive workup)

1. O3

2. Zn, H2O

what reaction are these reagents from?

ozonolysis (reductive workup)

which reaction?

ozonolysis (reductive workup)

ozonolysis reagents (oxidative workup)

1. O3

2. H2O2

or

KMnO4 (hot, conc), H3O+

1. O3

2. H2O2

what reaction are these reagents from?

ozonolysis (oxidative workup)

KMnO4 (hot, conc), H3O+

what reaction are these reagents from?

ozonolysis (oxidative workup)

Which reaction?

ozonolysis (oxidative workup)

hydrogenation reagents

H2, Pd-C or Pt or Ni

H2, Pd-C

what reaction are these reagents from?

hydrogenation

H2, Pt

what reaction are these reagents from?

hydrogenation

H2, Ni

what reaction are these reagents from?

hydrogenation

hydrogenation regiochemistry/stereochemistry

N/A, syn

which reaction?

hydrogenation

cyclopropanation reagents

CH2I2, Zn(Cu)

or

CHCl3, NaOH (strong base)

CH2I2, Zn(Cu)
what reaction are these reagents from?

cyclopropanation

CHCl3, NaOH (strong base)
what reaction are these reagents from?

cyclopropanation

cyclopropanation regiochemistry/stereochemistry

N/A, syn

which reaction?

cyclopropanation