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14. Explain why pyrrole is an electron-rich heterocycle that is activated toward electrophilic aromatic substitution, while pyridine is an electron poor heterocyclic that is deactivated toward electrophilic aromatic substitution.

14. Explain why pyrrole is an electron-rich heterocycle that is activated toward electrophilic aromatic substitution, while pyridine is an electron poor heterocyclic that is deactivated toward electrophilic aromatic substitution.

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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**Question 14:** Explain why pyrrole is an electron-rich heterocycle that is activated toward electrophilic aromatic substitution, while pyridine is an electron-poor heterocycle that is deactivated toward electrophilic aromatic substitution. --- **Explanation:** **Pyrrole** is an electron-rich heterocycle primarily because of the lone pair of electrons on the nitrogen atom. This lone pair is part of the aromatic sextet, contributing to the electron density of the ring, making pyrrole more reactive towards electrophilic aromatic substitution. **Pyridine**, on the other hand, is electron-poor. The nitrogen in pyridine is sp2 hybridized, with its lone pair in an sp2 orbital orthogonal to the aromatic π system. This configuration does not contribute electron density to the ring and instead makes nitrogen more electronegative, withdrawing electron density from the ring. As a result, pyridine is less reactive toward electrophilic substitution. In summary: - **Pyrrole:** Electron-rich, facilitates electrophilic aromatic substitution. - **Pyridine:** Electron-poor, resists electrophilic aromatic substitution.
Transcribed Image Text:**Question 14:** Explain why pyrrole is an electron-rich heterocycle that is activated toward electrophilic aromatic substitution, while pyridine is an electron-poor heterocycle that is deactivated toward electrophilic aromatic substitution. --- **Explanation:** **Pyrrole** is an electron-rich heterocycle primarily because of the lone pair of electrons on the nitrogen atom. This lone pair is part of the aromatic sextet, contributing to the electron density of the ring, making pyrrole more reactive towards electrophilic aromatic substitution. **Pyridine**, on the other hand, is electron-poor. The nitrogen in pyridine is sp2 hybridized, with its lone pair in an sp2 orbital orthogonal to the aromatic π system. This configuration does not contribute electron density to the ring and instead makes nitrogen more electronegative, withdrawing electron density from the ring. As a result, pyridine is less reactive toward electrophilic substitution. In summary: - **Pyrrole:** Electron-rich, facilitates electrophilic aromatic substitution. - **Pyridine:** Electron-poor, resists electrophilic aromatic substitution.
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