Ncert Exercises & Solutions

Question 13.7:-

Propanal and pentane-3-one are the ozonolysis products of an alkene? What is the structural formula of the alkene?

As per the given information, propanal and pentan-3-one are the ozonolysis products of an alkene. Let the given alkene be ‘A’. Writing the reverse of the ozonolysis reaction, we
get:

$H_{3} C - C H_{2} - C H O + C H_{2} - \underset{\underset{O}{∥}}{C} - C H_{2} - C H_{3}$
$P r o p a n a l ↑ Z n + H_{2} O P e n \tan t - 3 - o n e$
$' X'$
$O z o n i d e$
$↑$
$' A' + O_{3}$
$A l k e n e$

The products are obtained on the cleavage of ozonide ‘X’. Hence, ‘X’ contains both products in the cyclic form. The possible structure of ozonide can be represented as:

Now, ‘X’ is an addition product of alkene ‘A’ with ozone. Therefore, the possible structure of alkene ‘A’ is:

$H_{3} C - C H_{2} - C H = C - C H_{2} - C H_{3}$
$|$
$C H_{2} C H_{3}$

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