Reagents in Orgo for AlkEnes

mCPBA

Epoxidation

OsO₄

H₂O, NMO

syn dihydroxylation

X

???

X₂

Dihalogenation

anti

X₂

H₂O

Halohydrin formation

anti

HX

Hydrohalogenation

syn OR anti

HBr

Hydrohalogenation but specifically hydrobromination

(markovnikov)

H₂O

H₂SO₄, H₃O⁺

ACID-catalyzed hydration

syn OR anti

1) BH3, THF
2) H2O2, NaOH

(sorta base)-catalyzed hydration

1) Hydroboration

2) Oxydation

syn

1) O3

2) Me₂S

1) Ozonolysis

2) Reduction

Adds 2 Os + 1 H

1) O₃

2) Zn/H₃O⁺

1) Ozonolysis

2) Reduction

Adds 2 Os

1) O₃

2) H₂O₂

1) Ozonolysis

2) Oxydation

Adds 2 Os + 1 OH

CH₂I₂

Zn-Cu

Trans alkenes

Cycloproponation of trans alkenes

CH₂I₂

Zn-Cu

Cis alkenes

Cycloproponation of cis alkenes

HBr

RO-OR

Radical hydrobromination

(anti-markovnikov)

H₂O₂

??

1) Molecule + HA

2) Molecule + A^-

ACIDIC keto-enol tautomerization

*remember to push resonance before 1st step*

1) Molecule + OH^-

2) Molecule + H₂O

BASIC keto-enol tautomerization

*remember to push resonance inbetween steps*

cat.

Catalyst