When N,N-dimethylaniline is treated with chlorine and aluminum trichloride, ortho and para products are observed. However, when it is treated with a mixture of nitric acid and sulfuric acid, only the meta product is observed. Explain these curious results. [Hint: Nitrogen-containg compounds are bases; when bases are treated with acids, the conjugate acid is formed] H3C N CI CH3 + H3C N CH3 CI Cl₂/AICI 3 H3C CH3 HNO3/H₂SO4 H3C N CH3 NO₂

When N,N-dimethylaniline is treated with chlorine and aluminum trichloride, ortho and para products are observed. However, when it is treated with a mixture of nitric acid and sulfuric acid, only the meta product is observed. Explain these curious results. [Hint: Nitrogen-containg compounds are bases; when bases are treated with acids, the conjugate acid is formed] H3C N CI CH3 + H3C N CH3 CI Cl₂/AICI 3 H3C CH3 HNO3/H₂SO4 H3C N CH3 NO₂

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter11: Reactions Of Alkyl Halides: Nucleophilic Substitutions And Eliminations

Section11.SE: Something Extra

Problem 79AP

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