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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5:40 minutes

Problem 21c

Textbook Question

Draw the resonance contributors for the following radicals:
c.

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Identify the radical in the structure. The radical is located on the carbon atom adjacent to the cyclohexane ring. This carbon is part of an allylic system, meaning it is adjacent to a double bond, which allows for resonance stabilization.

Recognize that resonance contributors involve the movement of electrons. In this case, the unpaired electron on the radical can interact with the π-electrons of the double bond to form resonance structures.

Draw the first resonance structure by moving the π-electrons of the double bond towards the radical carbon. This creates a new double bond between the radical carbon and the adjacent carbon, while the original double bond shifts to the next carbon-carbon bond.

Draw the second resonance structure by moving the π-electrons of the new double bond further along the chain. This creates a double bond between the next two carbons, while the unpaired electron shifts to the terminal carbon of the chain.

Verify that all resonance contributors follow the rules of resonance: the overall charge and number of electrons remain the same, and the unpaired electron is delocalized across the π-system, providing stabilization to the radical.

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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 placement of electrons. These structures help illustrate the delocalization of electrons within a molecule, which can stabilize the overall structure. Understanding resonance is crucial for predicting the reactivity and stability of radicals and other reactive intermediates.

Radicals

Radicals are species that contain an unpaired electron, making them highly reactive. They can be formed through various processes, including homolytic bond cleavage. In the context of resonance, radicals can have multiple resonance contributors, which can influence their stability and reactivity, making it essential to analyze all possible structures.

Electron Delocalization

Electron delocalization refers to the distribution of electrons across multiple atoms in a molecule, rather than being localized between two atoms. This phenomenon is a key feature of resonance and contributes to the stability of radicals and other intermediates. Recognizing how electrons can be shared among different atoms helps in drawing accurate resonance contributors and understanding the overall behavior of the molecule.

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Related Practice

Textbook Question

Draw all possible resonance structures for the reactive intermediates shown.

(c)

Textbook Question

Draw the resonance contributors of the cyclooctatrienyl dianion.

a. Which of the resonance contributors is the least stable?

Textbook Question

Which is longer, the carbon–oxygen single bond in a carboxylic acid or the carbon–oxygen bond in an alcohol? Why?

Textbook Question

Draw resonance contributors for the following ions:

Textbook Question

Draw the resonance contributors for the following radicals:

Textbook Question

The given was missing some important resonance forms of the intermediates shown in brackets. Complete this mechanism by drawing all the resonance forms of these intermediates. Do your resonance forms help to explain why this reaction occurs under very mild conditions (water with a tiny trace of acid)?

Textbook Question

All of the rings of the four heterocyclic bases are aromatic. This is more apparent when the polar resonance forms of the amide groups are drawn, as is done for thymine here. Redraw the hydrogen-bonded guanine-cytosine and adenine-thymine pairs shown in Figure 23-24, using the polar resonance forms of the amides. Show how these forms help to explain why the hydrogen bonds involved in these pairings are particularly strong. Remember that a hydrogen bond arises between an electron-deficient hydrogen atom and an electron-rich pair of nonbonding electrons.

Textbook Question

Which of the following has delocalized electrons?

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Draw the resonance contributors for the following radicals:c.

Key Concepts

Resonance Structures

Radicals

Electron Delocalization

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Draw the resonance contributors for the following radicals:
c.