The diazonium tetrafluoroborate shown is heated to give an aryl fluoride (Balz-Schiemann), which is then oxidised with hot alkaline $KMnO X_{4}$ and acidified. Which structure is the final product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: D

The salt shown is 4-methylbenzenediazonium tetrafluoroborate. Thermal decomposition gives 4-fluorotoluene,

BF X_{3}

and

N X_{2}

. Alkaline permanganate then oxidises the side-chain methyl to a carboxylate, which gives 4-fluorobenzoic acid on acidification; the C-F bond is unaffected.

Practice Amines and Aromatic Nitrogen Compounds More on Diazonium, Sandmeyer and azo coupling products of drawn anilines

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The diazonium tetrafluoroborate shown is heated to give an aryl fluoride (Balz-Schiemann), which is then oxidised with hot alkaline KMnOX4​ and acidified. Which structure is the final product?

Answer: D

More questions on Diazonium, Sandmeyer and azo coupling products of drawn anilines

The diazonium tetrafluoroborate shown is heated to give an aryl fluoride (Balz-Schiemann), which is then oxidised with hot alkaline $KMnO X_{4}$ and acidified. Which structure is the final product?