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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1:46 minutes

Problem 48a

Textbook Question

Draw the resonance structure that would result from the indicated movement of electrons.
(a)

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Identify the starting structure and locate the electrons that are indicated to move. These could be lone pairs, π-bonds, or negative charges. Ensure you understand the direction of the arrow (from electron source to destination).

Determine the type of resonance movement indicated. Common types include: (1) lone pair to π-bond, (2) π-bond to lone pair, or (3) π-bond to π-bond. This will help you predict the new bonding arrangement.

Redraw the structure, showing the new position of the electrons after the indicated movement. Adjust the formal charges on atoms as necessary to reflect the redistribution of electrons.

Verify that the new structure follows the rules of resonance: (1) the total number of electrons remains the same, (2) the octet rule is satisfied for second-row elements, and (3) the overall charge of the molecule or ion is conserved.

Check for additional resonance structures by repeating the process for other possible electron movements, if applicable. This will help you identify all significant resonance contributors.

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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 ways of drawing the same molecule that illustrate the delocalization of electrons. They are used to represent molecules where the electron distribution cannot be depicted by a single Lewis structure. Each resonance structure contributes to the overall hybrid structure, which is more stable than any individual form.

Electron Movement

Electron movement in organic chemistry typically refers to the shifting of electron pairs during chemical reactions or when drawing resonance structures. This movement is often depicted using arrows, where a double-headed arrow indicates the movement of a pair of electrons, while a single-headed arrow shows the movement of a single electron. Understanding how electrons can move helps in predicting the stability and reactivity of molecules.

Stability of Resonance Structures

The stability of resonance structures is determined by factors such as the octet rule, charge distribution, and the presence of formal charges. More stable resonance structures have full octets for all atoms, minimal formal charges, and negative charges on more electronegative atoms. Evaluating the stability of these structures is crucial for predicting the behavior of molecules in chemical reactions.

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a. Draw the important resonance forms of the products of protonation on each of the three nitrogen atoms.

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For each of the molecules shown, do the following:

(i) Identify all pushable pairs.

(ii) Identify all places where electrons can be pushed.

(iii) Draw one valid resonance structure.

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