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

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
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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
'N
HNO3 / H₂SO4
H3C
N
CH3
NO₂
Transcribed Image Text: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 'N HNO3 / H₂SO4 H3C N CH3 NO₂
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