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

1. A Review of General Chemistry

Resonance Structures

Organic Chemistry

1. A Review of General Chemistry

Resonance Structures

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6:07 minutes

Problem 43d,e

Textbook Question

In the following sets of resonance forms, label the major and minor contributors and state which structures would be of equal energy. Add any missing important resonance forms.
(d)
(e)

Verified step by step guidance

Identify the resonance structures in each set. For set (d), the structures involve a nitro group and a carbanion. For set (e), the structures involve an amine group and a carbocation.

Evaluate the stability of each resonance structure. In set (d), the carbanion is more stable when it is adjacent to the electron-withdrawing nitro group, making it a major contributor. In set (e), the resonance structure with the positive charge on the more substituted carbon is more stable.

Determine the major and minor contributors. In set (d), the structure with the carbanion next to the nitro group is the major contributor. In set (e), the structure with the positive charge on the more substituted carbon is the major contributor.

Check for any missing resonance forms. In set (d), consider if there are any other possible resonance forms involving the movement of electrons. In set (e), consider if there are any other possible resonance forms involving the movement of electrons.

State which structures would be of equal energy. In set (d), the two structures are not of equal energy due to the differing stability of the carbanion positions. In set (e), the two structures are not of equal energy due to the differing stability of the carbocation positions.

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Key Concepts

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

Resonance Structures

Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. They help in understanding the actual electronic structure of a molecule, which is a hybrid of all possible resonance forms. The stability and contribution of each resonance form depend on factors like the octet rule, charge distribution, and the presence of electronegative atoms.

Major and Minor Contributors

In resonance theory, major contributors are the resonance forms that are more stable and thus have a greater influence on the overall structure of the molecule. Minor contributors are less stable forms that contribute less to the resonance hybrid. Factors such as formal charge, octet fulfillment, and the presence of electronegative atoms determine the stability of these contributors.

Equal Energy Structures

Equal energy structures refer to resonance forms that have the same energy level and thus contribute equally to the resonance hybrid. These forms typically have similar stability and do not favor one over the other. Identifying these structures is crucial for understanding the reactivity and properties of the molecule, as they can influence the distribution of electron density.

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In the following sets of resonance forms, label the major and minor contributors and state which structures would be of equal energy. Add any missing important resonance forms.(d) (e)

Key Concepts

Resonance Structures

Major and Minor Contributors

Equal Energy Structures

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In the following sets of resonance forms, label the major and minor contributors and state which structures would be of equal energy. Add any missing important resonance forms.
(d)
(e)