NaHSO 4
H 2 O
OsO 4 cold
O
ves the higher y lds.
OXID
cis-1,2-Cyclopentanediol
H H
HH
O
Os
O
O
+
HH
HO OH
(a meso compound)
- Osmium tetroxide gi ie
- Osmium tetroxide is highly toxic and is very expensive ⇒ Osmium tetroxide is
used catalytically in conjunction with a cooxidant.
sily causing
further oxidation of the glycol.
attempted by using cold, dilute, and basic solutions of potassium permanganate.
8.11 ATIVE CLEAVAGE OF ALKENES
- Alkenes with monosubstituted carbon atoms are oxidatively cleaved to salts of
carboxylic acids by hot basic permangnate solutions.
- Potassium permanganate is a very powerful oxidizing agent and is ea
1) Limiting the reaction to hydroxylation alone is often difficult but usually
CH 3 C O^4
−,
heat
H+ 2
(ci
.
H CHCH 3 CH 3 C
O
O−
KMn , OH H 2 O 2 CH
3 C
O
OH
s or trans) Acetate ion Acetic acid
1) The intermediate in this reaction may be a glycol that is oxidized further with
cleavage at the carbon-carbon bond.
2) Acidification of the mixture, after the oxidation is complete, produces 2 moles of
acetic acid for each mole of 2-butene
- The terminal CH 2 group of a 1-alkene is completely oxidized to carbon dioxide
and water by hot permanganate.
- A disubstituted carbon atom of a double bond becomes the carbonyl group of a
