Aldehydes and Ketones - Result Question 54

####64. An organic compound $A, C _6 H _{10} O$, on reaction with $CH _3 MgBr$ 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 $C$.

$(2000,5 M)$

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