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

11. Radical Reactions

Radical Stability

Organic Chemistry

11. Radical Reactions

Radical Stability

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1:42 minutes

Problem 65

Textbook Question

Ethers can be converted into radicals, some more easily than others. Which of the following radicals is more stable, and thus, more likely to form?

Verified step by step guidance

Understand the concept of radical stability: In organic chemistry, radicals are atoms or molecules that have unpaired electrons. The stability of a radical is influenced by several factors, including the presence of electron-donating groups, resonance stabilization, and hyperconjugation.

Identify the types of radicals: Ethers can form different types of radicals depending on the structure of the ether. Common radicals include primary, secondary, and tertiary radicals, as well as allylic and benzylic radicals.

Evaluate the stability of each radical: Generally, tertiary radicals are more stable than secondary radicals, which are more stable than primary radicals. This is due to hyperconjugation and the inductive effect of alkyl groups. Additionally, radicals that are resonance-stabilized, such as allylic and benzylic radicals, are particularly stable.

Consider resonance effects: If the radical can be stabilized by resonance, it will be more stable. For example, a benzylic radical is stabilized by the aromatic ring through resonance, making it more stable than a simple alkyl radical.

Compare the radicals: Based on the factors discussed, compare the radicals formed from the ether. Determine which radical has the greatest stability due to hyperconjugation, resonance, or other stabilizing effects.

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Key Concepts

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

Radical Stability

Radical stability is influenced by factors such as hyperconjugation, resonance, and the inductive effect. More stable radicals have lower energy and are more likely to form. Stability increases with the number of alkyl groups attached to the radical center, as they can donate electron density through hyperconjugation.

Hyperconjugation

Hyperconjugation is the delocalization of electrons in sigma bonds (typically C-H or C-C) adjacent to a radical center, which helps stabilize the radical. This effect is more pronounced in radicals with more alkyl substituents, as they provide more sigma bonds for electron delocalization, enhancing radical stability.

Resonance Stabilization

Resonance stabilization occurs when a radical can delocalize its unpaired electron over multiple atoms, typically through pi bonds. This delocalization lowers the energy of the radical, making it more stable. Radicals that can participate in resonance are generally more stable than those that cannot.

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Related Practice

Textbook Question

Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.

(b)

Textbook Question

Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.

(c)

Textbook Question

Why is a 2° carbon radical more stable than a 1° carbon radical?

Textbook Question

The following polyunsaturated fat, which does not exist in nature, is oxidized at a rate similar to oleic acid (Table 11.14), despite having two cis-alkenes. Why?

Textbook Question

Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.

(d)

Textbook Question

Methyl t-butyl ether (MTBE) is used preferentially over diethyl ether because it is less prone to form peroxides. Explain this observation in terms of the two structures.

Textbook Question

a. Which of the hydrogens in the structure in the margin is the easiest for a chlorine radical to remove?

b. How many secondary hydrogens does the structure have?

Textbook Question

Rank the following radicals in decreasing order of stability. Classify each as primary, secondary, or tertiary.

a. The isopentyl radical,

b. The 3-methyl-2-butyl radical,

c. The 2-methyl-2-butyl radical,

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