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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0:53 minutes

Problem 64e

Textbook Question

Two resonance structures are shown for each molecule. Use the arrow-pushing formalism to represent the electron flow from the structure on the left to the one on the right.
(e)

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Step 1: Identify the resonance structures. The structure on the left has a positively charged nitrogen atom and a negatively charged oxygen atom, while the structure on the right has a neutral nitrogen atom and a double bond between the carbon and oxygen.

Step 2: Locate the electron-rich and electron-deficient areas. The lone pairs on the oxygen atom in the left structure are electron-rich, and the positively charged nitrogen atom is electron-deficient.

Step 3: Use the arrow-pushing formalism to show electron flow. Begin by moving one lone pair of electrons from the oxygen atom to form a double bond with the adjacent carbon atom.

Step 4: To maintain the octet rule, move the π electrons from the carbon-nitrogen double bond toward the nitrogen atom, converting the nitrogen atom into a neutral species with a lone pair.

Step 5: Verify the resulting resonance structure. The new structure should have a neutral nitrogen atom with a lone pair and a double bond between the carbon and oxygen, consistent with the structure on the right.

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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 that cannot be accurately depicted by a single Lewis structure. Each resonance structure contributes to the overall hybrid structure, which is a more accurate representation of the molecule's electron distribution.

Arrow-Pushing Formalism

Arrow-pushing formalism is a method used in organic chemistry to depict the movement of electrons during chemical reactions and resonance. Curved arrows indicate the direction of electron flow, showing how electrons are added or removed from bonds or atoms. This technique helps visualize the changes in electron density and the formation of new bonds.

Electron Delocalization

Electron delocalization refers to the spreading of electron density across multiple atoms in a molecule, rather than being localized between two specific atoms. This phenomenon is crucial in resonance structures, as it stabilizes the molecule by allowing electrons to be shared among several atoms, leading to lower energy configurations and increased stability.

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Related Practice

Textbook Question

Determine whether the following pairs of structures are actually different compounds or simply resonance forms of the same compounds.

Textbook Question

Determine whether the following pairs of structures are actually different compounds or simply resonance forms of the same compounds.

Textbook Question

Determine whether the following pairs of structures are actually different compounds or simply resonance forms of the same compounds.

Textbook Question

The following compound can become protonated on any of the three nitrogen atoms. One of these nitrogens is much more basic than the others, however.

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

Textbook Question

Each pair of structures represents two valid resonance structures. Use the arrow-pushing formalism to justify the formation of the one on the left from the one on the right.

(a)

Textbook Question

Each pair of structures represents two valid resonance structures. Use the arrow-pushing formalism to justify the formation of the one on the left from the one on the right.

(b)

Textbook Question

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

(a)

Textbook Question

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.

(a)

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