Q. 52d E - Organic Chemistry (Mcmurry)

Question

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

$d. CH{}_{3}C{H}_{2}C=OC{H}_{2}C{H}_{2}C{H}_{2}C{H}_{2}C{O}_{2}H$

Step-by-Step Solution

Answer

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

d. Formation of  $CH{}_{3}C{H}_{2}C=OC{H}_{2}C{H}_{2}C{H}_{2}C{H}_{2}C{O}_{2}H$