Question

What are the major organic products when the following molecule is treated with ozone and then with \[\dfrac{{Zn}}{{{H_2}O}}\]?

A.

B.

C.

D.

Answer 1

Hint: When an alkene is treated with ozone followed by a reducing agent to break the complex double bond containing compounds into the smaller and more identifiable products. Ozonolysis is a type of weak oxidative cleavage where alkenes are cleaved (double bonds) into either ketones, aldehydes or carboxylic acid using ozone \[\left( {{O_3}} \right)\].

Complete step by step answer:
Ozonolysis is a method of oxidatively cleaving alkenes or alkynes using ozone \[\left( {{O_3}} \right)\], a reactive allotrope of oxygen. The process allows for carbon-carbon double or triple bonds to be replaced by double bonds with oxygen. Aldehydes (CHO), and ketones \[\left( {C{H_3}COC{H_3}} \right)\] can be formed through reductive workup.
We know that the carbon-carbon double bond is broken and we are forming a carbon-oxygen double bond on each of the two carbons that originally composed the alkene. we will end up with a ketone. And this on hydrolysis in the presence of Zinc gives aldehyde.
The given molecule in the question is methylene (methylene cyclohexane) and when this molecule is treated with ozone and then with \[\dfrac{{Zn}}{{{H_2}O}}\], a carbonyl group, having a carbon-to-oxygen double bond named cyclohexanone and formic acid are formed.
The reaction is shown below:

Therefore, the correct answer is option (A).

Note: Ozonolysis also occurs naturally and would break down repeated units used in rubber and other polymers. On an industrial scale, azelaic acid and pelargonic acids are produced from ozonolysis. Ozonolysis, or “oxidative cleavage” was originated in the 1800’s by the inventor, Christian Friedrich Schoenlein. The reaction also is attributed to Carl Dietrich Harries; therefore, we can hear a reaction termed “Harries ozonolysis”.