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Br Br2 Br (minor) HNO3, H2SO4 (major) NON2

Br Br2 Br (minor) HNO3, H2SO4 (major) NON2

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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When N,N-dimethylaniline is treated with bromine, no catalyst is required (why not?), and 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 after a neutralizing reaction workup. Explain these results—draw mechanistic details, including intermediates, to support your explanation. ### Reactions Illustrated: - **Top Reaction:** - Reagent: Br₂ - Products: - ortho-brominated N,N-dimethylaniline (minor) - para-brominated N,N-dimethylaniline (major) - **Bottom Reaction:** - Reagents: HNO₃, H₂SO₄ - Product: meta-nitro N,N-dimethylaniline ### Explanation: In the first reaction, the lack of a catalyst for the bromination indicates that N,N-dimethylaniline's electron-donating group facilitates electrophilic aromatic substitution. This enhances the reactivity of the benzene ring, leading to ortho and para substitution. The major product is para due to steric hindrance. In the second reaction, the presence of acid catalyzes nitration, and the meta product is favored. The acidic conditions likely protonate the nitrogen, reducing the electron-donating ability of the N,N-dimethylamino group and directing substitution to the meta position.
Transcribed Image Text:When N,N-dimethylaniline is treated with bromine, no catalyst is required (why not?), and 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 after a neutralizing reaction workup. Explain these results—draw mechanistic details, including intermediates, to support your explanation. ### Reactions Illustrated: - **Top Reaction:** - Reagent: Br₂ - Products: - ortho-brominated N,N-dimethylaniline (minor) - para-brominated N,N-dimethylaniline (major) - **Bottom Reaction:** - Reagents: HNO₃, H₂SO₄ - Product: meta-nitro N,N-dimethylaniline ### Explanation: In the first reaction, the lack of a catalyst for the bromination indicates that N,N-dimethylaniline's electron-donating group facilitates electrophilic aromatic substitution. This enhances the reactivity of the benzene ring, leading to ortho and para substitution. The major product is para due to steric hindrance. In the second reaction, the presence of acid catalyzes nitration, and the meta product is favored. The acidic conditions likely protonate the nitrogen, reducing the electron-donating ability of the N,N-dimethylamino group and directing substitution to the meta position.
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