ORGANIC CHEMISTRY

(OZONOLYSIS)

The reaction of alkene or Alkyne with ozone (O3) followed by hydrolysis is known as ozonolysis.
It is two types : (I) Reductive ozonolysis In presence of reducing agent
(II) Oxidative ozonolysis In presence of oxidising agent
Reducing agents : Zn, H2O or Zn, CH3COOH or (CH3)2S or (Ph)3P etc.
Oxidising agents : H2O2 or R C O O H or Ag2O etc.
||
O
R R’ R O R’ Zn / H O R
O3 2
C=C C C Reductive C=O + R’–C–H
step I
R H –70°C R H ozonolysis R
O O O

Oxidative [SCT- Cut the double bond

Example 1 : ozonolysis H2O2 and paste two oxgen atoms
and vice versa]
R–C–R + R’–C–OH
O O
Mechanism :
R
R
R R O R C O R’
O
C O C O + C=O
+ O R
C R’ C O H
R’ H O
H

R
R
O R—C—O
C O
R O
R’ R–C–R + R’–C–H
O
O=C C
H R’ O O
H
Note : In case of oxidative ozonolysis aldehyde (not ketone) further undergoes oxidation which gives
acid as product.

Q.1 Give the product of the following reaction.

(i ) O3 (i ) O3
(i) H2C = CH2 (ii) CH3–CH = CH2
(ii ) Zn / H 2O (ii ) Zn / H 2O

CH 3
|
(i ) O3 (i ) O3
(iii) CH 3 C CH 2 (iv)
(ii ) Zn / H 2O (ii ) Zn / H 2O

(i ) O3 (i ) O3
(v) (vi)
(ii ) Zn / H 2O (ii ) Zn / H 2O
H
(i ) O3
(vii) H2C=CH–CH2–CH=CH–CH3
(ii ) Zn / H 2O
Q.2 Find out the structure of reactant.
H
(i) X (i ) O3
CH 3 CH 2 C H (ii) X (i ) O3 O + O
(ii ) Zn / H 2O || (ii ) Zn / H 2O H
O
H O
O
(i ) O3 O (i ) O3
(iii) X O+ (iv) X +
(ii ) Zn / H 2O (ii ) Zn / H 2O
H H

O
CH3 H
(i ) O3 (i ) O3
(v) X O (vi) X + C=O + C=O
(ii ) Zn / H 2O (ii ) Zn / H 2O
H3C H
O
O
(i ) O3 (i ) O3 O
(vii) X (viii) X O + HCHO
(ii ) Zn / H 2O (ii ) Zn / H 2O
O C10H12
O
O
(i ) O3
O
(ix) X + O=C=O + O + HCHO
(ii ) Zn / H 2O
C12 H18
O O
(i ) O3 (i ) O3
(x) C6 H 4 C3H2O3 (xi) X + HCHO
( X) (ii ) Zn / H 2O
C12H18 (ii ) Zn / H 2O

O
Q.3 Give the ozonolysis product of the following.
H
O3 ( ) O3 O3 /
(i) X 3O C H (ii) ? (iii)
Zn Zn / H 2 O Zn / H 2 O

O
How many species. How many species are found.
Q.4 How mnay ozonoids are possible in given reaction.
(i ) O3 (i ) O3
(i) CH2 = CH2 (ii ) Zn / H 2O
(ii) CH3 – CH = CH – CH3 (ii ) Zn / H 2O

(i ) O3
(iii) CH3 – CH = CH2 (ii ) Zn / H 2O

Q.5 The reactants that lead to product (a) and (b) on ozonolysis are

HCHO

(a) (b)

(A) (B) (C) (D)

Q.6 Which starting material should be used to produce the compound shown below?

O3
?
Zn H 2O

(A) (B) (C) (D)

Q.7 This compound on ozonolysis gives which of the following compounds

O
||
(I) (II) OHC C C CH 2 C CHO
|| ||
O O

O
||
(III) CHO (IV) OHC C C CH 2 CH O
| ||
CHO O
(A) I, II, III & IV (B) I, III, IV (C) I, II, III (D) I, II, IV