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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6:41 minutes

Problem 6c

Textbook Question

Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.
c.

Verified step by step guidance

Identify the species in question and determine if it has resonance structures. Resonance occurs when there are delocalized electrons, such as lone pairs, π-bonds, or charges, that can be redistributed across the molecule.

Draw all possible resonance contributors for the species. To do this, move electrons (using curved arrows) while ensuring that the octet rule is satisfied for second-row elements and that formal charges are minimized. Use MathML to represent the structures if needed.

Evaluate the stability of each resonance contributor. Contributors with a full octet on all atoms, minimal formal charges, and negative charges on more electronegative atoms are more stable and contribute more to the resonance hybrid.

Rank the resonance contributors in order of decreasing contribution to the resonance hybrid based on their stability. The most stable contributor will have the highest contribution, while less stable contributors will contribute less.

Draw the resonance hybrid by combining the resonance contributors. Use dashed lines to represent delocalized π-bonds and partial charges to indicate the distribution of charge across the molecule.

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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 Lewis structures for the same molecule that depict the same arrangement of atoms but differ in the placement of electrons. These structures help illustrate the delocalization of electrons within a molecule, which contributes to its stability. The actual structure of the molecule is a resonance hybrid, a weighted average of all valid resonance forms.

Resonance Hybrid

The resonance hybrid is the most stable representation of a molecule, combining the characteristics of all its resonance structures. It reflects the delocalization of electrons, resulting in bond lengths and angles that are intermediate between those predicted by individual resonance forms. The hybrid is often depicted with dashed lines to indicate partial bonds and charges.

Contribution to Resonance Hybrid

The contribution of each resonance structure to the resonance hybrid is determined by factors such as the stability of the structure, the octet rule, and the presence of formal charges. Structures that minimize formal charges and maintain full octets for all atoms are generally more significant contributors. Ranking these structures helps predict the overall electron distribution in the molecule.

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Related Practice

Textbook Question

Draw resonance contributors for the following ions:

Textbook Question

a. Predict the relative bond lengths of the three carbon–oxygen bonds in the carbonate ion.

b. What is the charge on each oxygen?

Textbook Question

Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.

Textbook Question

Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.

Textbook Question

Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.

Textbook Question

Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.

Textbook Question

Which of the following has delocalized electrons?

Textbook Question

Draw all resonance structures of the following carbanion and carbocation.

(a)

(b)

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