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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Problem 40a

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.

Verified step by step guidance

Identify the three nitrogen atoms in the compound: N1 (leftmost), N2 (rightmost), and N3 (top). Each nitrogen can potentially be protonated.

Consider protonation at N1: Add a proton (H⁺) to N1, forming a positive charge on N1. Draw resonance structures by moving the lone pair electrons from N1 to form a double bond with the adjacent carbon, and adjust the electrons on the other atoms accordingly.

Consider protonation at N2: Add a proton (H⁺) to N2, forming a positive charge on N2. Draw resonance structures by moving the lone pair electrons from N2 to form a double bond with the adjacent carbon, and adjust the electrons on the other atoms accordingly.

Consider protonation at N3: Add a proton (H⁺) to N3, forming a positive charge on N3. Draw resonance structures by moving the lone pair electrons from N3 to form a double bond with the adjacent carbon, and adjust the electrons on the other atoms accordingly.

Evaluate the stability of the resonance structures: The nitrogen with the most stable resonance forms upon protonation is the most basic. Consider factors such as the ability to delocalize the positive charge and the electronegativity of the atoms involved.

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Key Concepts

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

Basicity of Nitrogen Atoms

Basicity refers to the ability of a compound to accept protons (H+). In the context of nitrogen atoms, their basicity is influenced by factors such as hybridization, steric hindrance, and the presence of electron-donating or withdrawing groups. In the given compound, the nitrogen atom that is more basic can accept a proton more readily due to its electronic environment.

Protonation and Resonance

Protonation is the addition of a proton to a molecule, which can significantly alter its structure and reactivity. In the case of nitrogen atoms, protonation can lead to the formation of positively charged ammonium ions. The resonance forms of these products illustrate how the positive charge can be delocalized across different nitrogen atoms, affecting the stability and reactivity of the resulting species.

Resonance Structures

Resonance structures are different ways of drawing a molecule that represent the same compound, showing the delocalization of electrons. For the compound in question, drawing resonance forms after protonation on each nitrogen atom helps visualize how the positive charge can be distributed among the nitrogens, which is crucial for understanding the stability and reactivity of the protonated species.

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Related Practice

Textbook Question

Draw the important resonance forms for the following molecules and ions.

(a) CO₃^2–

(b)

(c)

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

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)

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)

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