Textbook Question
Provide the mechanism of the radical reactions shown.
(b)
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Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
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Mullins 1st EditionCh. 11 - Properties and Synthesis of Alkyl Halides: Radical ReactionsProblem 54
Mullins 1st EditionCh. 11 - Properties and Synthesis of Alkyl Halides: Radical ReactionsProblem 54Chapter 10, Problem 54
The following ethers are ranked according to their ability to form explosive peroxides. Explain this ranking based on your knowledge of the reaction mechanism.
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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.
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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.
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The radical stability trend.
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.
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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.
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Related Practice
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The solvent tetrahydrofuran (THF) is often sold with a small amount of BHT added. Provide a mechanism that explains why this might be so.
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Textbook Question
If a small amount of a moderately nonpolar poisonous compound was added to a pond, why would it be safer to drink the water than it would be to eat the fish that live there?
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Textbook Question
Provide the mechanism of the radical reactions shown.
(a)
1015
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Textbook Question
Other molecules can be used as initiators in radical reactions. One such molecule is 2, 2'-azobisisobutyronitrile (AIBN). Show an arrow-pushing mechanism that rationalizes the formation of the following radical species. What are the driving forces of this reaction?
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Textbook Question
One danger associated with storing ether solvents is their tendency to form explosive peroxides when exposed to oxygen. Suggest a mechanism by which the hydroperoxide might form. You can assume the presence of X• to start the reaction.
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