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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Transcribed Image Text:**Explain why the following reaction sequence will not occur:**
The image illustrates a proposed chemical reaction involving aniline (a benzene ring with an -NH₂ group) reacting under nitration conditions, with concentrated nitric acid (HNO₃) and sulfuric acid (H₂SO₄) as catalysts, supposedly forming p-nitroaniline.
**Explanation:**
1. **Aniline Reactivity:**
- Aniline is a benzene ring substituted with an amino group (-NH₂), which is an electron-donating group.
- Under typical nitration conditions, strong acids like H₂SO₄ can protonate the -NH₂ group, forming an anilinium ion (-NH₃⁺).
- This transformation changes the electron-donating nature of the amino group to electron-withdrawing, significantly reducing the ring's activation for subsequent electrophilic substitution reactions, such as nitration.
2. **Reaction with HNO₃ and H₂SO₄:**
- The combination of HNO₃ and H₂SO₄ forms the nitronium ion (NO₂⁺), a strong electrophile required for nitration. However, the deactivated benzene ring in anilinium (due to protonation) is less likely to undergo nitration.
- Additionally, aniline can undergo side reactions under these strongly acidic conditions, potentially leading to polymerization or degradation rather than the intended introduction of a nitro group.
Because of these factors, nitration of aniline in the described conditions is unlikely to proceed directly to form p-nitroaniline. Knowledge of reaction mechanisms and effects of substituents on aromatic rings is crucial in predicting the feasibility of such reaction sequences.
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