OSMIUM TETROXIDE

SYN ADDITION GIVES CIS GLYCOLS

CH3
CH3
OsO4

H2O

OH

NaHSO3

OH

CH3
C
CH3 C
H

H
OsO4

CH3
H2O

CH3

N aHSO3

remember: addition is
result is

cis

syn

C H OH
OH

cis -2-butene

cis

syn
conformation

meso

What is the result with

trans -2-butene?

MECHANISM

..

:O
:O
..

Os

..
O:

: O : .. : O :

O
.. :

:O
..

Os

NaHSO3 /H2O
Both of the hydroxyl
oxygens in the glycol
come from OsO4

O:

..

Notice the
transfer of
2e- onto Os
= REDUCTION
of Osmium

hydrolysis
OXIDIZED

H O
O H
HO .. OH
further reduced
Os
REDUCED
Os + 4H2O
O
O
: ..
NaHSO
.. :
3

POTASSIUM PERMANGANTE

MECHANISM

..

..
O:

:O
:O
..

: O : .. : O :

Mn

+
K
O
: .. :

O
: ..

Mn

H2O

KMnO4

:O
.. :hydrolysis
oxidized

purple

MnO2
brown sludge

H O
O H
HO .. OH
Mn
O
: ..
:O
.. :

reduced

CH3
CH3

H
OH

KMnO4

dilute, neutral, 0oC

H
CH3
C
CH3 C
H

OH
CH3

CH3
KMnO4

dilute, neutral, 0oC

Same result as with OsO4.

cis
H

C H OH
OH

meso

What is the result with

trans -2-butene?