Textbook Question
Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.
(c)
2
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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 15
Mullins 1st EditionCh. 11 - Properties and Synthesis of Alkyl Halides: Radical ReactionsProblem 15Chapter 10, Problem 15
A radical reaction, as it progressed through its propagation steps, involved the following radical species. Suggest which products might form in all possible termination steps (six products are possible).
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Identify the radical species involved in the reaction. In the image, we have a tin radical (Sn·) and a bromine radical (Br·), as well as an ethyl radical (·CH2CH3).
Understand that in a radical termination step, two radicals combine to form a stable molecule. This process removes radicals from the reaction mixture.
Consider all possible pairings of the radicals to form stable products. The radicals can pair as follows: Sn· with Br·, Sn· with ·CH2CH3, and Br· with ·CH2CH3.
For each pairing, draw the resulting molecule. For example, when Sn· and Br· combine, they form an organotin bromide compound.
Repeat the process for all possible combinations, ensuring that each radical is paired with every other radical at least once. This will result in six possible termination products.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Radical Reaction Mechanism
Radical reactions involve species with unpaired electrons, known as radicals. These reactions typically proceed through three stages: initiation, propagation, and termination. In the termination step, radicals combine to form stable products, ceasing the radical chain process. Understanding these stages is crucial for predicting possible products in radical reactions.
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Radical Chain Reaction Mechanism.
Termination Steps in Radical Reactions
Termination steps occur when two radical species combine to form a stable, non-radical product. This step is essential in radical reactions as it determines the final products formed. In the given image, radicals such as Sn· and Br· can combine in various ways, leading to different termination products, which are crucial for understanding the reaction's outcome.
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12:11Radical Chain Reaction Mechanism.
Radical Stability and Reactivity
Radical stability is influenced by factors such as the presence of electron-donating groups and the type of atom bearing the radical. More stable radicals are less reactive, affecting the likelihood of certain termination products. In the image, the stability of Sn· and Br· radicals will guide which combinations are more favorable, impacting the prediction of possible products.
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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.
(a)
8
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Textbook Question
Provide a mechanism for the chlorination of cyclohexane. Be sure to include initiation, propagation, and three possible termination steps.
1
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Textbook Question
Specify the conditions that would allow the synthesis of the 1° and 3° bromoalkanes from the same starting alkene.
1
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Textbook Question
Halohydrin formation is a stereospecific reaction. Identify the products of halohydrin formation of the following diastereomeric alkenes to demonstrate this stereospecificity.
1
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Textbook Question
Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.
(b)
2
views