Q. 52b E - Organic Chemistry (Mcmurry)

Question

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

$b. \left(C{H}_3\right)2C=O +C{H}_{3}C{H}_{2}C{H}_{2}C{O}_{2}H$

Step-by-Step Solution

Answer

(b).  2 methyl pent-2-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 .

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

Step2: Structure of alkene while undergoing oxidation

(b).   Formation of  $C{H}_{3}C=O +C{H}_{3}C{H}_{2}C{H}_{2}C{O}_{2}H$