Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

19. Reactions of Aromatics: EAS and Beyond

Diazo Sequence Groups

Organic Chemistry

19. Reactions of Aromatics: EAS and Beyond

Diazo Sequence Groups

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4:28 minutes

Problem 29

Textbook Question

Explain why a diazonium group on a benzene ring cannot be used to direct an incoming substituent to the meta position.

Verified step by step guidance

Understand the role of the diazonium group (-N≡N⁺) on a benzene ring. The diazonium group is an electron-withdrawing group due to the positive charge on the nitrogen atom and the triple bond, which pulls electron density away from the benzene ring.

Recall the concept of electrophilic aromatic substitution (EAS). In EAS, the position of substitution is influenced by the electronic effects of substituents already present on the benzene ring. Electron-withdrawing groups typically direct incoming substituents to the meta position, while electron-donating groups direct them to the ortho and para positions.

Analyze the resonance structures of the benzene ring with the diazonium group. The diazonium group does not have resonance structures that stabilize the carbocation intermediate at the meta position during EAS. Instead, it stabilizes the carbocation intermediates at the ortho and para positions through resonance effects.

Recognize that the diazonium group is unique compared to other electron-withdrawing groups. While most electron-withdrawing groups direct substituents to the meta position, the diazonium group stabilizes the ortho and para positions due to its ability to delocalize positive charge through resonance.

Conclude that the diazonium group on a benzene ring cannot direct an incoming substituent to the meta position because it stabilizes the ortho and para positions through resonance effects, making these positions more favorable for substitution.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Diazonium Group

A diazonium group is a functional group characterized by the presence of a nitrogen atom bonded to a benzene ring, typically represented as -N2+. It is highly reactive and can participate in various electrophilic aromatic substitution reactions. However, its presence on the benzene ring influences the reactivity and orientation of incoming substituents due to its electron-withdrawing nature.

Electrophilic Aromatic Substitution (EAS)

Electrophilic aromatic substitution is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. The directing effects of substituents are crucial in determining the position of the incoming electrophile. Substituents can be classified as ortho/para-directing or meta-directing based on their electronic effects, which influence the stability of the intermediate carbocation formed during the reaction.

Ortho/Para vs. Meta Directing Effects

Substituents on a benzene ring can direct new substituents to specific positions based on their electronic properties. Ortho and para directing groups, such as -OH or -NH2, donate electron density, stabilizing the carbocation intermediate at these positions. In contrast, the diazonium group, being electron-withdrawing, destabilizes the carbocation at the meta position, making it unfavorable for substitution to occur there.

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