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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5:32 minutes

Problem 45b

Textbook Question

Draw the important resonance forms of the following free radicals.
b.

Verified step by step guidance

Identify the free radical in the given structure. In this case, the free radical is located on the CH2 group attached to the benzene ring.

Recognize that the benzene ring can participate in resonance with the free radical. The unpaired electron on the CH2 group can interact with the π-electrons of the benzene ring.

Draw the first resonance form by moving the unpaired electron from the CH2 group to form a double bond with the adjacent carbon of the benzene ring. This will result in the movement of the π-electrons in the benzene ring.

Continue the resonance by moving the π-electrons around the benzene ring. This will create a new resonance form where the unpaired electron is now located on a different carbon atom in the benzene ring.

Repeat the process to generate additional resonance forms, ensuring that the unpaired electron is delocalized around the benzene ring, which stabilizes the free radical through resonance.

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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. In the case of free radicals, resonance can help distribute the unpaired electron across multiple atoms, stabilizing the radical. Understanding how to draw these structures is crucial for predicting the reactivity and stability of the molecule.

Free Radicals

Free radicals are species that contain an unpaired electron, making them highly reactive. They can be formed through various processes, including the homolytic cleavage of covalent bonds. In organic chemistry, understanding the behavior of free radicals is essential for predicting reaction mechanisms and outcomes, especially in radical substitution reactions.

Aromatic Stability

Aromatic compounds, like benzene, exhibit unique stability due to their cyclic structure and delocalized π electrons. This stability influences the behavior of substituents, including free radicals, on the aromatic ring. Recognizing how resonance and aromaticity contribute to the stability of radicals is key to understanding their reactivity in organic reactions.

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Related Practice

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.

(f)

Textbook Question

Identify the resonance structure that will be produced given the molecule shown and the electron flow indicated.

(a)

Textbook Question

Identify the resonance structure that will be produced given the molecule shown and the electron flow indicated.

(c)

Textbook Question

Draw the important resonance forms of the following free radicals.

(c)

(d)

Textbook Question

Draw the important resonance forms of the following free radicals.

Textbook Question

Acetonitrile (CH₃C≡N) is deprotonated by very strong bases. Write resonance forms to show the stabilization of the carbanion that results.

Textbook Question

Allylic halides have the structure

b. Draw the resonance structures of the allylic cations formed by ionization of the following halides.

(i)

(ii)

Textbook Question

3-Bromocyclohexene is a secondary halide. It undergoes S_N1 substitution about as fast as most tertiary halides. Use resonance structures to explain this enhanced reactivity.

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Draw the important resonance forms of the following free radicals. b.

Key Concepts

Resonance Structures

Free Radicals

Aromatic Stability

Watch next

Draw the important resonance forms of the following free radicals.
b.