Q. 52a E - Organic Chemistry (Mcmurry)

Question

Show the structures of alkenes that give the following products on oxidative cleavage with in acidic solution:

$a. C{H}_{3}C{H}_{2}C{O}_{2}H + C{O}_2$

Step-by-Step Solution

Answer

1. But-1-ene

Step1: Oxidation by K M n O 4

${\mathbf{KMnO}}_{\mathbf{4}}$ is a strong oxidising agent. In oxidative cleavage,${\mathbf{KMnO}}_{\mathbf{4}}$ leads to the formation of 1,2-diol which leads to formation of the carboxylic acid and ${\mathbf{KMnO}}_{\mathbf{4}}$ is converted to brown ${\mathbf{MnO}}_{\mathbf{2}}$.

The colour changes from purple to brown and diol lead to produce two adjacent alcoholic groups 

Step2: Structure of alkene while undergoing oxidation

1. Formation of  ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}\text{H} \text{ + } {\text{CO}}_{\text{2}}$