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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6:08 minutes

Problem 10d

Textbook Question

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

Verified step by step guidance

Identify the compound's structure and locate any pi bonds or lone pairs that can participate in resonance. These are typically found in conjugated systems or near electronegative atoms.

Draw the initial Lewis structure of the compound, ensuring all atoms have the correct number of valence electrons and formal charges are minimized.

Identify possible resonance contributors by moving electrons from pi bonds or lone pairs to adjacent atoms, ensuring that the octet rule is not violated for second-row elements.

Draw the resonance structures, showing the movement of electrons with arrows. Indicate the formal charges on atoms where necessary.

Analyze the resonance structures to determine areas of high electron density (where electrons are localized or delocalized) and low electron density (where positive charges or electron deficiency is present).

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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 a molecule that depict the same arrangement of atoms but differ in the distribution of electrons. They help illustrate the delocalization of electrons within a molecule, which can affect its stability and reactivity. Understanding resonance is crucial for identifying areas of electron density.

Electron Density

Electron density refers to the probability of finding electrons in a particular region of a molecule. Areas of high electron density are typically associated with negative charges or lone pairs, while areas of low electron density may be associated with positive charges or electron-deficient atoms. Resonance structures help visualize these variations in electron density.

Lewis Structures

Lewis structures are diagrams that represent the bonding between atoms of a molecule and the lone pairs of electrons that may exist. They are essential for understanding resonance, as they provide a basis for drawing resonance structures by showing how electrons can be rearranged while maintaining the same atomic connectivity.

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Related Practice

Textbook Question

For each of the following compounds, draw the important resonance forms. Indicate which structures are major and minor contributors or whether they have the same energy.

Textbook Question

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

(c)

Textbook Question

For each of these ions, draw the important resonance forms and predict which resonance form is likely to be the major contributor.

(a)

Textbook Question

For each of the following compounds, draw the important resonance forms. Indicate which structures are major and minor contributors or whether they have the same energy.

(d) [H₂CNO₂]^–

Textbook Question

For each of these ions, draw the important resonance forms and predict which resonance form is likely to be the major contributor.

(b)

Textbook Question

For each of these ions, draw the important resonance forms and predict which resonance form is likely to be the major contributor.

(c)

Textbook Question

For each of the following compounds, draw the important resonance forms. Indicate which structures are major and minor contributors or whether they have the same energy.

(e) [CH₃C(OH)₂]⁺

(f) [CH₂CHNH]^–

Textbook Question

For each of the following compounds, draw the important resonance forms. Indicate which structures are major and minor contributors or whether they have the same energy.

(g)

(h)

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

Key Concepts

Resonance Structures

Electron Density

Lewis Structures

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