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Q. 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 $C$.

IIT JEEIIT JEE 2000Aldehydes Ketones and Carboxylic Acids

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