The compound shown is heated with hot alkaline KMnO4 and then acidified; the product is treated with Br2 and FeBr3. Which structure is the final product?

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JEE Advanced levelSingle correct optionDifficulty 3 of 3o2271

The compound shown is heated with hot alkaline $KMnO X_{4}$ and then acidified; the product is treated with $Br X_{2}$ and $FeBr X_{3}$ . Which structure is the final product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: A

The compound is isopropylbenzene (cumene). Hot

KMnO X_{4}

oxidises the benzylic C-H alkyl side chain to

- COOH

, giving benzoic acid. The carboxyl group is deactivating and meta-directing, so bromination gives 3-bromobenzoic acid, whereas brominating cumene first would give para/ortho products.

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The compound shown is heated with hot alkaline KMnOX4​ and then acidified; the product is treated with BrX2​ and FeBrX3​. Which structure is the final product?

Answer: A

More questions on EAS major product and directing effects in drawn benzenes

The compound shown is heated with hot alkaline $KMnO X_{4}$ and then acidified; the product is treated with $Br X_{2}$ and $FeBr X_{3}$ . Which structure is the final product?