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

Previous problemNext problem

6:37 minutes

Problem 54

Textbook Question

The following ethers are ranked according to their ability to form explosive peroxides. Explain this ranking based on your knowledge of the reaction mechanism.

Verified step by step guidance

Understand the structure of ethers: Ethers are organic compounds containing an oxygen atom connected to two alkyl or aryl groups. Their general formula is R-O-R', where R and R' can be the same or different groups.

Recognize the formation of peroxides: Ethers can form peroxides when exposed to oxygen over time. This occurs through a radical mechanism where the ether reacts with oxygen to form a hydroperoxide, which can further react to form explosive peroxides.

Identify factors affecting peroxide formation: The ability of an ether to form peroxides is influenced by the stability of the radical intermediate formed during the reaction. Ethers with more stable radicals are more prone to peroxide formation.

Consider steric and electronic effects: Ethers with bulky groups may hinder the approach of oxygen, reducing peroxide formation. Conversely, ethers with electron-donating groups can stabilize the radical intermediate, increasing peroxide formation.

Apply this knowledge to rank ethers: Analyze the structure of each ether in the problem, considering the factors above. Rank them based on the likelihood of forming stable radical intermediates and thus explosive peroxides.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Ether Structure and Stability

Ethers are organic compounds characterized by an oxygen atom connected to two alkyl or aryl groups. The stability of ethers is influenced by the steric and electronic effects of these groups. Bulky groups can hinder peroxide formation by providing steric hindrance, while electron-donating groups can stabilize the ether, reducing its reactivity towards peroxide formation.

Peroxide Formation Mechanism

Peroxide formation in ethers typically occurs through a radical chain mechanism initiated by the abstraction of a hydrogen atom, forming a radical that reacts with oxygen. This process is more favorable in ethers with less steric hindrance and more accessible hydrogen atoms, as these conditions facilitate the initial radical formation and subsequent reactions with oxygen.

Radical Stability

The stability of radicals formed during peroxide formation is crucial in determining the likelihood of peroxide formation. Radicals are stabilized by resonance and hyperconjugation, which can be influenced by the substituents on the ether. Ethers with substituents that stabilize radicals will more readily form peroxides, as the intermediate radicals are more stable and persistent.

Watch next

Master The radical stability trend. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

For each set of reactive intermediates, rank them in order of reactivity (1 = most reactive).

(b)

Textbook Question

Use the information in Table 4-2 to explain why toluene (PhCH₃) has a very high octane rating of 111. Write an equation to show how toluene reacts with an alkyl free radical to give a relatively stable radical.

Textbook Question

A student adds NBS to a solution of 1-methylcyclohexene and irradiates the mixture with a sunlamp until all the NBS has reacted. After a careful distillation, the product mixture contains two major products of formula C₇H₁₁Br.

b. Rank these three intermediates from most stable to least stable.

Textbook Question

Explain the dramatic difference in rotational energy barriers of the following three alkenes. (Hint: Consider what the transition states must look like.)

Textbook Question

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

(a)

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?

Show more practices