Organic Chemistry 1 Reagents

hydrogenation

H2, Pt

Syn only

Adds H & H

Hydrohalogenation (Markovnikov)

HX, CCl4

adds “X” & “X”

anti & syn

hydrohalogenation (anti-Markovnikov)

HX, ROOR

adds H & “X”

anti & syn

halogenation

X2, CCl4

anti-addition only

adds “X” & “X”

halohydrin formation

X2, H2O

anti addition of OH and X

acid-catalyzed hydration

H2SO4, H2O

H & H and Markovnikov OH

Anti + syn (+E)

Oxymercuration-Demercuration

1) Hg(OAc)2, H2O

2) NaBH4

Adds H & OH

anti only

mark addn.

Hydroboration-Oxidation

1. BH3, THF

2. H2O2, NaOH

Adds H & OH

anti-mark addn.

syn only

epoxidation

mCPBA

O across double bond

syn only

Ozonolysis

1) O3, CH2CL2, -78C

2) DMS

Adds Carbonyls (splits double bond into 2 double bonds)

Syn-Dihydroxylation

KMnO4, NaOH Cold

OR

1) OsO4

2) Na2SO3

syn addition of OH & OH

Anti-Dihydroxylation

(1) MCPBA

2) H2SO4, H2O (w/ epoxide)

anti addition of OH & OH