Chem 14D

Regiochem: Markovnikov

Stero: none

Reagents (HX): HCl, HBr, HI

Products: X + H

Regiochemistry: Markovnikov

Stereochemistry: none

Reagents: H2SO4, H3PO4, HCl, H3O+

Products: OH + H

Regiochemistry: none

Stereochemistry: syn

Reagents: MCPBD, MMPP, RCO3H (CH3COOH)

Forms O

MCPBA/ H3O+ —> anti Markovnikov

Product: O

Regiochemistry: markovnikov

Stereochemistry: anti

Reagents: Hg(OAc)2, NaBH4, H20

Product: OH

Regiochemistry: anti-markovnikov

Stereochemistry: none

Reagents: HBr/ROOR

Product: Br + H

Regiochemistry: anti-markovnikov

Stereochemistry: syn addition

Reagents: 1) BH₃, THF (2) H2O2, NaOH, OH^-

Product: H + OH

Regiochemistry: none

Stereochemistry: syn addition

Reagents: H2/ Pt, Pd, Ni

Product: H + H

Regiochemistry: none

Stereochemistry: anti-addition

Reagents: 1. Br2/ CCl4 or CH2CL2

Product: Br + Br

Regiochemistry: Markovnikov

Stereochemistry: anti-addition

Reagents: X2(Cl, Br, I)/H20 or ROH

Product: X + OH

Regiochemistry: none

Stereochemistry: anti-addition

Reagents: 1. RCOOH / 2. H3O+

Product: OH + OH

Regiochemistry: none

Stereochemistry: Syn

Reagents: 1. OsO₄/ 2. NaHSO₃, H₂O or KMnO₄/OH- (cold) or OsO4/Na₂SO₃, H₂O

Product: OH + OH

Reducing

- reagents: 1. O3/ 2. (CH3)2 S or Zn/H2O

- product: O-H

Oxidizing

- Reagents: O3/H2O2

Product: OH + O