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When N,N-dimethylaniline is treated with bromine, ortho

Chapter 19, Problem 19.83

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QUESTION:

When N,N-dimethylaniline is treated with bromine, ortho and para products are observed. Yet, when N,N-dimethylaniline is treated with a mixture of nitric and sulfuric acid, only the meta product is observed. Explain these curious results. N NO2 HNO3 H2SO4 N N Br N Br Br2 +

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QUESTION:

When N,N-dimethylaniline is treated with bromine, ortho and para products are observed. Yet, when N,N-dimethylaniline is treated with a mixture of nitric and sulfuric acid, only the meta product is observed. Explain these curious results. N NO2 HNO3 H2SO4 N N Br N Br Br2 +

ANSWER:

Step 1 of 2

Amino group is a strongly activating ortho-para director, and so it’s no surprise that exposure to molecular bromine leads to both ortho and para brominated isomers.

   

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