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 16a
Mullins 1st EditionCh. 11 - Properties and Synthesis of Alkyl Halides: Radical ReactionsProblem 16aChapter 10, Problem 16a
Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.
(a) 
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 plays a crucial role in determining the bond-dissociation energy.
Identify the types of radicals formed: When a bond is broken, two radicals are formed. The stability of these radicals can be influenced by factors such as resonance, hyperconjugation, and the presence of electron-withdrawing or electron-donating groups.
Evaluate the stability of the radicals: More stable radicals are typically formed from bonds with lower bond-dissociation energies. Stability can be assessed by considering the number of resonance structures, the degree of hyperconjugation, and the presence of stabilizing groups.
Compare the radicals from each bond pair: For each pair of bonds, compare the stability of the radicals formed. The bond that forms less stable radicals will generally have a higher bond-dissociation energy.
Predict the bond with higher bond-dissociation energy: Based on the stability analysis, predict which bond in each pair will have the higher bond-dissociation energy. The bond forming less stable radicals will require more energy to dissociate.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Bond-Dissociation Energy
Bond-dissociation energy is the energy required to break a bond in a molecule, resulting in the formation of radicals. It is a measure of bond strength; higher energy indicates a stronger bond. Understanding this concept helps predict which bonds are more stable and less likely to dissociate.
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How to calculate enthalpy using bond dissociation energies.
Radical Stability
Radical stability refers to the ability of a radical to exist without undergoing further reactions. Stability is influenced by factors such as resonance, hyperconjugation, and the electronegativity of atoms involved. More stable radicals are typically formed from weaker bonds, which have lower bond-dissociation energies.
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Resonance
Resonance is the delocalization of electrons across adjacent atoms, which can stabilize radicals by spreading out the electron density. Molecules with resonance structures often have lower bond-dissociation energies because the resulting radicals are more stable. Recognizing resonance can help predict radical stability and bond strength.
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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)
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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.
1432
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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).
889
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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.
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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)
1009
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