reagents

Hydrohalogenation Reagent:

HX (X = Cl, I, Br)

Hydrohalogenation

Can carbocation shift. Markovnikov

Radical hydroboration Reagent:

Hbr, ROOR (peroxide)

radical Hydroboration

Cannot carbocation shift. Anti Markovnikov. Only works with Br

Acid catalyzed hydration Reagent:

H2O, H2SO4 (acid catalyst)

Acid catalyzed hydration

Can carbocation shift. Markovnikov

Alcohol addition Reagent:

ROH, H+

Alcohol addition

Can carbocation shift. Markovnikov.

Oxymercuration reduction Reagent:

1.) Hg(OAc)2, H2O

2.) NaBH4

Oxymercuration reduction

Cannot carbocation shift. Markovnikov

Hydroboration oxidation Reagent:

1.) BH3•THF

2.) H2O2, NaOH

Hydroboration oxidation

Cannot carbocation shift. Anti-Markovnikov. Syn specific

Halogenation (dihalogenation) Reagent:

X2 (Cl or Br)

Halogenation (dihalogenation)

Cannot carbocation shift. Anti specific

Halohydrin formation Reagent:

X2 (Cl or Br) and H2O

Halohydrin

Cannot carbocation shift. OH on more substituted carbon. Anti specific

Epoxidation Reagent:

mCPBA, or RCO3H

Epoxidation

Cannot carbocation shift. Syn specific

Dihydroxylation Reagent:

1.) OsO4

2.) NaHSO3,H2O

OR

1.) Cold KMnO4

2.) NaOH, H2O

Dihydroxylation

Cannot carbocation shift. Syn specific

Ozonolysis reduction Reagent:

1.) O3

2.) Zn OR CH3SCH3

Ozonolysis oxidative work up Reagent:

1.) O3

2.) H2O2

Ozonolysis oxidative work up

Cleaves double bond, adds carboxylic acid

Ozonolysis reductive

Cleaves carbon double bond. Makes aldehyde/ketone

Hydrogenation Reagent:

H2

Pt/Pd/Ni catalyst

Hydrogenation

Cannot carbocation shift. Syn specific