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

8. Elimination Reactions

Nucleophiles and Basicity

Organic Chemistry

8. Elimination Reactions

Nucleophiles and Basicity

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Problem 29

Textbook Question

The zwitterionic form of carbonyls is often used to explain their electrophilicity. Draw the zwitterionic structure of NO⁺₂. Why is this such a great electrophile at the central nitrogen?

Verified step by step guidance

Step 1: Begin by analyzing the structure of NO+2 (nitronium ion). It consists of a nitrogen atom bonded to two oxygen atoms, with a formal positive charge on the nitrogen. Both oxygen atoms are double-bonded to nitrogen, and the molecule is linear due to sp hybridization of the nitrogen atom.

Step 2: To draw the zwitterionic form, consider the resonance structures of NO+2. One resonance structure involves shifting electron density from one of the oxygen atoms toward the nitrogen, creating a formal negative charge on the oxygen and a formal positive charge on the nitrogen. This highlights the electrophilic nature of the nitrogen atom.

Step 3: The zwitterionic form emphasizes the separation of charges within the molecule. Represent the nitrogen with a positive charge and one oxygen with a negative charge, while the other oxygen remains neutral. This charge separation increases the molecule's reactivity.

Step 4: The central nitrogen in NO+2 is a great electrophile because it carries a formal positive charge, making it electron-deficient. Electrophiles are species that seek electrons, and the positive charge on nitrogen strongly attracts nucleophiles.

Step 5: Additionally, the resonance stabilization of NO+2 ensures that the positive charge on nitrogen is delocalized, making the molecule stable yet highly reactive. This combination of stability and electron deficiency enhances its electrophilic character.

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Key Concepts

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

Zwitterionic Structures

A zwitterion is a molecule that has both positive and negative charges but is overall neutral. In the context of carbonyls, zwitterionic forms can stabilize charge separation, enhancing the molecule's reactivity. Understanding how to draw and interpret these structures is crucial for analyzing their electrophilic properties.

Electrophilicity

Electrophilicity refers to the ability of a species to accept electrons, making it a key player in chemical reactions, particularly in nucleophilic attacks. The presence of a positive charge or electron-deficient atom increases a molecule's electrophilicity, which is essential for understanding why certain structures, like zwitterions, are highly reactive.

Nitrogen's Role in Electrophilicity

In the zwitterionic structure of NO₂⁺, the central nitrogen atom is positively charged, making it a strong electrophile. This positive charge results from the nitrogen's ability to form multiple bonds with electronegative oxygen atoms, leading to a significant electron deficiency that attracts nucleophiles during chemical reactions.

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