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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6:30 minutes

Problem 45e,f

Textbook Question

For each pair of ions, determine which ion is more stable. Use resonance forms to explain your answers.
(e)
(f)

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Identify the ions in each pair: In set (e), we have two carbocations, and in set (f), we have two enolate ions.

For set (e), analyze the resonance stabilization: The carbocation adjacent to the double bond can be stabilized by resonance. Draw the resonance structures for each ion to see which one has more resonance forms.

For set (e), compare the resonance forms: The ion with more resonance forms is more stable because the positive charge is delocalized over a larger area, reducing the energy of the system.

For set (f), analyze the resonance stabilization: The enolate ion can be stabilized by resonance between the oxygen and the carbon atoms. Draw the resonance structures for each ion to see which one has more resonance forms.

For set (f), compare the resonance forms: The ion with more resonance forms is more stable because the negative charge is delocalized over a larger area, reducing the energy of the system.

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Key Concepts

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

Resonance

Resonance is a concept in organic chemistry that describes the delocalization of electrons in molecules. It occurs when a molecule can be represented by two or more valid Lewis structures, known as resonance forms. These forms contribute to the overall hybrid structure, which is more stable than any individual resonance form. Understanding resonance is crucial for predicting the stability of ions and molecules, as it allows for the distribution of charge and electron density.

Stability of Ions

The stability of ions is influenced by several factors, including charge distribution, electronegativity, and resonance. Generally, ions that can delocalize their charge through resonance are more stable than those that cannot. In the context of the question, comparing the stability of the two ions involves analyzing how effectively each ion can distribute its positive charge through resonance structures, which ultimately affects their reactivity and stability.

Electrophilicity

Electrophilicity refers to the tendency of a species to accept electrons, making it a key factor in determining the reactivity of ions. In the case of positively charged ions, a more stable ion is typically less electrophilic because its positive charge is better stabilized through resonance. Understanding electrophilicity helps in predicting how these ions will interact with nucleophiles and other reactive species in organic reactions.

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Related Practice

Multiple Choice

Which is NOT a valid resonance contributor of acetamide?

Multiple Choice

Based on the resonance contributors, which atom is most likely to react with an acidic proton, H⁺?

Multiple Choice

Which is the correct arrow pushing formalism to convert between the following resonance contributors?

Multiple Choice

Which resonance contributor of acetic acid actually exists?

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)

Textbook Question

Use resonance structures to identify the areas of high and low electron density in the following compounds:

(a)

(b)

(c)

Textbook Question

Draw the important resonance forms to show the delocalization of charges in the following ions. In each case, indicate the major resonance form(s).

(j)

(k)

Textbook Question

b. Draw the resonance forms for ozone (bonded O–O–O)

c. Sulfur dioxide has one more resonance form than ozone. Explain why this structure is not possible for ozone.

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For each pair of ions, determine which ion is more stable. Use resonance forms to explain your answers.(e) (f)

Key Concepts

Resonance

Stability of Ions

Electrophilicity

Watch next

For each pair of ions, determine which ion is more stable. Use resonance forms to explain your answers.
(e)
(f)