1) es are not usually isolated but are reduced directly by treatment with znic
and acetic acid (HOAc).
eduction produces carbonyl comp
safely isolated and identified.
Ozonid
2) The r ounds (aldehydes or ketones) that can be
O
C
O
C + Zn HOAc C
O
O + O C + Zn(HOAc) 2
ldehydes and/or ketones
3.
Ozonide A
3-28-02
The overall process of onzonolysis is:
CC
R R"
C O
R
+
3 2 2 − o R"
R' H R'
O C
H
- O , CHCl, 78 C
- Zn/HOAc
1) The –H attached to the double bond is not oxidized to –OH as it is with
permanganate oxidations
CH 3 C
CH 3
CHCH 3
- O 3 , CH 2 Cl 2 , − 78 oC
2. Zn/HOAc CH^3 C
CH 3
O CH 3 CH
O
+
2-Methyl-2-butene Acetone Acetaldehyde
CH 3 C
CH 3
CH CH 3 C
CH 3
CH + HCH
3-Methyl-1-butene Isobutyraldehyde Formaldehyed
CH 2
- O 3 , CH 2 Cl 2 , − 78 oC
- Zn/HOAc
O O
8.12 ADDITION OF BROMINE AND CHLORINE TO LKYNES
- Alkynes show the same kind of reactions toward chlorine and bromine that
alkenes do: They react by addition.
of halogen employed.
A
1) With alkynes, the addition may occur once or twice depending on the number of
molar equivalents
