Question

From among the following, identify the compound which forms two moles of a ketone on ozonolysis.

• A. 2,3-Dimethylbutane.
• B. 3-Methyl-1-pentene.
• C. 2,3-Dimethyl-2-butene.
• D. 2-Methyl-2-pentene.

Hint:

In ozonolysis, a symmetrical alkene will give two identical carbonyl products, whereas an asymmetrical alkene will form a mixture of products (often an aldehyde and a ketone).

Answer 1

The Correct Option is C

Ozonolysis is a reaction of alkenes with ozone (\(O_3\)), which leads to the formation of carbonyl compounds, typically aldehydes or ketones. In the case of 2,3-Dimethyl-2-butene, the ozonolysis reaction leads to the formation of two moles of a ketone. Let's break it down: 1. Structure of 2,3-Dimethyl-2-butene: - The compound 2,3-Dimethyl-2-butene is a symmetric alkene with the double bond at the second carbon. The structure is as follows: \[ \text{CH}_3-\text{C}(\text{CH}_3)-\text{CH}=\text{CH}_2 \] 2. Ozonolysis Mechanism: - In ozonolysis, the alkene reacts with ozone (\(O_3\)), and the double bond is cleaved, forming two molecules of a carbonyl compoun(D) - Since the alkene is symmetric, the result will be two identical ketones, each containing a carbonyl group on a separate carbon atom. 3. Resulting Products: - The ozonolysis of 2,3-Dimethyl-2-butene gives two moles of acetone (\(CH_3COCH_3\)), which is a ketone. - Therefore, the correct compound is 2,3-Dimethyl-2-butene, as it leads to the formation of two moles of a ketone (acetone) during ozonolysis. Thus, the correct answer is (C) 2,3-Dimethyl-2-butene.