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Bromination of Toluene

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If you treat toluene with 2 equivalences of bromine, you will get aminly 2,4-dibromotoluene and not 2, 6-dibromotoluene. However, you can produce 3, 5-dibromotoluene by treating 4-aminotoluene with 2 equivalences of bromine. Then first treating the product, 4-amino-3,5-dibromotoluene, with HNO2 in H2SO4, and secondly treating the resulting product with hypophosphorus acid, H3PO2. Fully explain why this series of reaction will produce the 3,5-dibromotoluene and direct bromination of toluene produces the 2,4-dibromotoluene.

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Solution Preview

See the attached file.
Bromination of toluene gives the wrong isomers.
Presence of methyl (-CH3) group makes the benzene ring o and p directiong. Because ortho and para substitution products are favored over meta, -CH3 is called an "ortho,para-director"? it "directs" ...

Solution Summary

This solution explains the concept behind different product formation during bromination of toluene by two different pathways.

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