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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4:53 minutes

Problem 46i,j

Textbook Question

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

Verified step by step guidance

Begin by identifying the pi bonds and lone pairs in the given compounds. These are the primary contributors to resonance structures.

Draw the initial Lewis structure for each compound, ensuring all atoms have complete octets where applicable.

Identify possible resonance structures by moving electrons from pi bonds or lone pairs to adjacent atoms, forming new pi bonds or lone pairs. Ensure that the overall charge of the molecule remains unchanged.

For each resonance structure, determine the areas of high electron density (typically where lone pairs or negative charges are located) and low electron density (typically where positive charges or electron-deficient atoms are located).

Compare the resonance structures to identify the most stable structure, which often has the least charge separation and places negative charges on more electronegative atoms. This will help pinpoint the areas of high and low electron density in the compound.

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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 distribution of electrons. These structures help illustrate the delocalization of electrons within a molecule, which can affect its stability and reactivity. Understanding resonance is crucial for predicting the behavior of compounds, especially in terms of electron density distribution.

Electron Density

Electron density refers to the probability of finding electrons in a given region of a molecule. Areas of high electron density are typically associated with negative charges or lone pairs, while low electron density areas may correspond to positive charges or electron-deficient sites. Analyzing electron density is essential for understanding molecular interactions, reactivity, and the stability of resonance structures.

Delocalization

Delocalization is the phenomenon where electrons are spread out over several atoms rather than being localized between two atoms. This occurs in systems with resonance, where multiple structures contribute to the overall electron distribution. Delocalization can enhance the stability of a molecule and influence its chemical properties, making it a key concept in understanding resonance and electron density.

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Related Practice

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)

Textbook Question

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

Textbook Question

Draw the resonance contributors of the cyclooctatrienyl dianion.

b. Which of the resonance contributors makes the smallest contribution to the hybrid?

Textbook Question

a. Draw resonance contributors for the following species, showing all the lone pairs:

b. For each species, indicate the most stable resonance contributor.

3. NO₂^-

Textbook Question

i) Which of the following resonance structures represents the 'actual' structure of the molecule shown? (ii) Which contributes more to the resonance hybrid? (iii) Why?

(a)

(b)

(c)

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?

10.

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

Key Concepts

Resonance Structures

Electron Density

Delocalization

Watch next

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