Question

An organic compound $A,C_6{H}_{10}O$, on reaction with $C{H}_{3}MgBr$ followed by acid treatment gives compound $B$. The compound $B$ on ozonolysis gives compound $C$, which in presence of a base gives 1-acetyl cyclopentane $D$. The compound $B$ on reaction with $HBr$ gives compound $E$. Write the structures of $A,B,C$ and $E$. Show, how $D$ is formed from $C$.

Answer 1