Textbook Question
Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.
(d)
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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 16b
Mullins 1st EditionCh. 11 - Properties and Synthesis of Alkyl Halides: Radical ReactionsProblem 16bChapter 10, Problem 16b
Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.
(b) 
Verified step by step guidance1
Understand the concept of bond-dissociation energy: Bond-dissociation energy is the energy required to break a bond in a molecule, resulting in the formation of radicals. The stability of the resulting radicals can influence the bond-dissociation energy.
Identify the radicals formed: When a bond is broken, two radicals are formed. The stability of these radicals is crucial in determining the bond-dissociation energy.
Evaluate radical stability: More stable radicals generally result in lower bond-dissociation energy because less energy is required to form them. Stability can be influenced by factors such as resonance, hyperconjugation, and the presence of electron-withdrawing or electron-donating groups.
Compare the stability of radicals: For each pair of bonds, compare the stability of the radicals formed upon bond dissociation. Consider factors like resonance stabilization, inductive effects, and steric hindrance.
Predict the bond with higher bond-dissociation energy: The bond that forms less stable radicals upon dissociation will have a higher bond-dissociation energy, as more energy is required to break the bond and form the less stable radicals.
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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 refers to the ability of a radical to exist without reacting further. Stability is influenced by factors such as hyperconjugation, resonance, and the electronegativity of the atom bearing the unpaired electron. More stable radicals are less reactive, which can affect the bond-dissociation energy of the bond from which they are formed.
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The radical stability trend.
Bond-Dissociation Energy
Bond-dissociation energy is the energy required to break a bond homolytically, resulting in the formation of radicals. It is a measure of bond strength; stronger bonds have higher dissociation energies. The stability of the resulting radicals can influence this energy, as more stable radicals typically result from weaker bonds.
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Hyperconjugation
Hyperconjugation is a stabilizing interaction that occurs when electrons in sigma bonds (usually C-H or C-C) delocalize into an adjacent empty or partially filled p-orbital or pi-system. This effect can stabilize radicals by dispersing the unpaired electron's charge, thereby influencing the bond-dissociation energy of the bond from which the radical is formed.
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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.
(c)
2
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Textbook Question
Using the bond-dissociation energies in Table 5.6,
(a) predict whether or not a fluorine radical would be selective for forming a single radical from propane.
2
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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.
(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.
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Textbook Question
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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