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.
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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 57
Mullins 1st EditionCh. 11 - Properties and Synthesis of Alkyl Halides: Radical ReactionsProblem 57Chapter 10, Problem 57
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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Identify the structure of 2,2'-azobisisobutyronitrile (AIBN) and note the azo group (N=N) in the center of the molecule. This group is key to the radical formation.
Understand that the reaction is initiated by heat, which provides the energy needed to break the N=N bond homolytically, resulting in the formation of two radicals.
Use arrow-pushing to show the homolytic cleavage of the N=N bond. Draw arrows starting from the bond and pointing towards each nitrogen atom, indicating the movement of one electron to each nitrogen.
Recognize that the driving force of this reaction is the formation of nitrogen gas (N₂), which is a very stable molecule. The release of N₂ gas provides a thermodynamic push for the reaction to proceed.
Illustrate the final step where the nitrogen radicals are released as nitrogen gas, and the remaining carbon-centered radicals are formed. These radicals can then participate in further radical reactions.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Radical Reactions
Radical reactions involve species with unpaired electrons, known as radicals, which are highly reactive. These reactions typically proceed through three main steps: initiation, propagation, and termination. Understanding how radicals form and react is crucial for analyzing mechanisms, such as those involving AIBN, which generates radicals that can initiate polymerization or other reactions.
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What are Radical Initiators?
Arrow-Pushing Mechanism
The arrow-pushing mechanism is a method used to depict the movement of electrons during chemical reactions. Arrows indicate the direction of electron flow, helping to visualize bond formation and breaking. This technique is essential for illustrating the steps in radical reactions, allowing students to understand how intermediates are formed and how the overall reaction progresses.
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Driving Forces of Reactions
Driving forces in chemical reactions refer to the factors that favor the progression of a reaction towards products. These can include thermodynamic stability, such as the formation of stable products or the release of energy (exothermic reactions). In radical reactions, the formation of stable radical intermediates and the overall decrease in energy can serve as significant driving forces, influencing the reaction pathway and outcome.
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Related Practice
Textbook Question
Tributyltin hydride (Bu3SnH) is often used as a 'radical carrier' in radical reactions. Which bond would you expect to be weaker, Sn–H or C–H? How might this relate to radical stability? Explain your answer.
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Textbook Question
Haloalkanes can be reduced to alkanes using radical reactions involving Bu₃SnH and a catalytic amount of AIBN. Suggest a mechanism for this reaction. [Pay close attention to the bonds formed and broken in developing your mechanism.]
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Textbook Question
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
Cyclizations can be carried out under radical conditions involving Bu₃SnH and a catalytic amount of AIBN. Suggest a mechanism for this reaction. [Pay close attention to the bonds formed and broken in developing your mechanism. It may be helpful to number the carbons.]
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