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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2:26 minutes

Problem 71d

Textbook Question

Which resonance contributor in each pair makes the greater contribution to the resonance hybrid?
d.

Verified step by step guidance

Identify the resonance contributors in the given pair. Resonance contributors are different Lewis structures that represent the same molecule or ion, differing only in the placement of electrons (not atoms).

Evaluate the stability of each resonance contributor. Stability is influenced by factors such as the octet rule, formal charges, and electronegativity. For example, a structure where all atoms satisfy the octet rule is generally more stable.

Check the formal charges on each resonance contributor. Structures with fewer formal charges or charges that are minimized are more stable. Additionally, negative charges are more stable on more electronegative atoms, while positive charges are more stable on less electronegative atoms.

Consider charge separation. Resonance contributors with less charge separation (i.e., fewer positive and negative charges spread across the molecule) are generally more stable and contribute more to the resonance hybrid.

Determine which resonance contributor is more stable based on the above criteria. The more stable resonance contributor will make the greater contribution to the resonance hybrid.

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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 is crucial for understanding its stability and reactivity. The actual molecule is a resonance hybrid, a weighted average of all valid resonance structures.

Resonance Hybrid

The resonance hybrid is the actual structure of a molecule that is represented as a combination of its resonance contributors. It reflects the delocalization of electrons across multiple bonds, leading to increased stability. The contribution of each resonance structure to the hybrid depends on factors like formal charge, electronegativity, and the overall stability of the structure.

Factors Affecting Resonance Contribution

Several factors determine the contribution of a resonance structure to the resonance hybrid, including the stability of the structure, the presence of formal charges, and the arrangement of electrons. Structures with minimal formal charges, full octets, and more electronegative atoms bearing negative charges are generally more stable and thus contribute more significantly to the resonance hybrid.

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Related Practice

Textbook Question

a. Draw resonance contributors for the following species. Do not include structures that are so unstable that their contributions to the resonance hybrid would be negligible. Indicate which are major contributors and which are minor contributors to the resonance hybrid.

b. Do any of the species have resonance contributors that all contribute equally to the resonance hybrid?

12.

Textbook Question

b. Do any of the species have resonance contributors that all contribute equally to the resonance hybrid?

13.

Textbook Question

b. Do any of the species have resonance contributors that all contribute equally to the resonance hybrid?

15.

Textbook Question

Which resonance contributor in each pair makes the greater contribution to the resonance hybrid?

Textbook Question

Draw another resonance form for each of the substituted allylic cations shown in the preceding figure, showing how the positive charge is shared by another carbon atom. In each case, state whether your second resonance form is a more important or less important resonance contributor than the first structure. (Which structure places the positive charge on the more-substituted carbon atom?)

Textbook Question

Draw the Lewis structure of azidomethane (CH₃N₃) [Show two important resonance structures.]

Textbook Question

b. Do any of the species have resonance contributors that all contribute equally to the resonance hybrid?

14.

Textbook Question

b. Do any of the species have resonance contributors that all contribute equally to the resonance hybrid?

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Which resonance contributor in each pair makes the greater contribution to the resonance hybrid? d.

Key Concepts

Resonance Structures

Resonance Hybrid

Factors Affecting Resonance Contribution

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Which resonance contributor in each pair makes the greater contribution to the resonance hybrid?
d.