Orgo 1 Exam 3

Hydrogenation

Syn; H2/Pd in ethanol

Halogenation

Anti; X2

Hydration

Syn or Anti; Markovnikov; forms a carbocation; H2O/H3PO4 (acid catalyzed)

Oxymercuration/Demercuration

Anti; Markovnikov; no carbocation formed; 1. Hg(OAc)2/H2O 2. NaBH4

Hydroboration Oxidation

Syn; Anti-Markovnikov; BH3/THF/H2O2

Halohydrin Formation

Anti; Markovnikov; Br2/H2O or NBS/H2O/DMSO

Epoxidation

Syn; makes cyclopropane; 1. X2/H2O 2. NaOH (base) or 1. mCPBA/CH2Cl2

Hydroxylation of Epoxides

Anti; H3O+/H2O (acid)

Syn-1,2-diols

Syn; 1. OsO4/pyridine 2. NaSO3/H2O

Addition of Carbenes

Syn; 1. CHCl3 2. KOH

Simmons-Smith

Syn; 1. CH2I2 2. Zn(Cu)

Ozonolysis

1. O3 2. Zn/H3O+

Oxidation

KMnO4/H3O+ ; carboxylic acids

Double Dehalogenation

KOH (base); alkyne synthesis