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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6:30 minutes

Problem 61a,b,c

Textbook Question

Which of the following has delocalized electrons?
a.
b.
c.

Verified step by step guidance

Step 1: Understand the concept of delocalized electrons. Delocalized electrons are electrons that are not associated with a single atom or a single covalent bond. Instead, they are spread out over multiple atoms, typically in a conjugated π-system or within a resonance structure.

Step 2: Identify the structural features that allow for delocalization. Look for conjugated systems, which are alternating single and double bonds, or resonance structures where electrons can move between atoms.

Step 3: Analyze each option (a, b, c) to determine if it contains a conjugated π-system or resonance structures. For example, check if there are alternating double and single bonds or lone pairs that can participate in resonance.

Step 4: Use resonance structures to confirm delocalization. Draw possible resonance forms for each option to see if electrons can be delocalized across multiple atoms.

Step 5: Based on the analysis, identify which option(s) have delocalized electrons. Ensure that the structure satisfies the criteria for delocalization, such as the presence of a conjugated system or resonance stabilization.

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Key Concepts

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

Delocalized Electrons

Delocalized electrons are electrons that are not confined to a single atom or bond but are spread over multiple atoms. This phenomenon occurs in molecules with conjugated systems or resonance structures, where the electron density is shared among several atoms, leading to increased stability and unique chemical properties.

Resonance Structures

Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. These structures help to represent the actual electron distribution more accurately, as the true structure is a hybrid of all possible resonance forms, contributing to the molecule's stability and reactivity.

Conjugation

Conjugation refers to the overlap of p-orbitals across adjacent double or triple bonds, allowing for the delocalization of electrons. This arrangement enhances the stability of the molecule and can affect its color, reactivity, and other physical properties, making it a key concept in understanding organic compounds.

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Related Practice

Textbook Question

Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.

Textbook Question

Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.

Textbook Question

Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.

Textbook Question

Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.

Textbook Question

Draw all resonance structures of the following carbanion and carbocation.

(a)

(b)

Textbook Question

How many atoms share the unpaired electron in semiquinone?

Textbook Question

Draw the resonance contributors for the following radicals:

Textbook Question

Another way the preceding might be presented is to say that the minor resonance structure(s) reveal the reactivity of a molecule. Show how the minor resonance structure(s) can help us understand that the following reactions occur with the regioselectivity shown.

(a)

(b)

(c)

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