Domanda del libro di testo
Using the bond-dissociation energies in Table 5.6,
(a) predict whether or not an iodine radical would be selective for forming a single radical propane.
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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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TOC.tableOfContents
- 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 1: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes 2: 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 1: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification 2: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution 1: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution 2: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems 1: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems 2: Pericyclic Reactions54
- Ch. 23 - Benzene 1: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene 2: 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: 9780137566471Non è quello che usi tu?Cambia libro di testo
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Mullins 1st EditionCh. 11 - Properties and Synthesis of Alkyl Halides: Radical ReactionsProblema 16d
Mullins 1st EditionCh. 11 - Properties and Synthesis of Alkyl Halides: Radical ReactionsProblema 16dCapitolo 10, Problema 16d
Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.
(d) 
Guida verificata passo dopo passo1
Identify the two molecules in the image: one is a bromocyclohexane and the other is an allylic bromide.
Understand that bond-dissociation energy is related to the stability of the radicals formed when the bond is broken. More stable radicals result in lower bond-dissociation energy.
Consider the stability of the radicals formed: breaking the C-Br bond in bromocyclohexane forms a cyclohexyl radical, while breaking the C-Br bond in the allylic bromide forms an allylic radical.
Recall that allylic radicals are stabilized by resonance, which allows the unpaired electron to be delocalized over the π system, increasing stability.
Conclude that the allylic radical is more stable than the cyclohexyl radical due to resonance stabilization, suggesting that the C-Br bond in bromocyclohexane has a higher bond-dissociation energy.
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Radical Stability
Radical stability is crucial in determining bond-dissociation energy. More stable radicals form from weaker bonds, as they require less energy to break. Stability is influenced by factors like hyperconjugation and resonance. In the given image, the radical formed from the allylic bromine bond benefits from resonance stabilization, making it more stable than the cyclohexyl radical.
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03:43
The radical stability trend.
Bond-Dissociation Energy
Bond-dissociation energy is the energy required to break a bond homolytically, forming radicals. It is higher for bonds that produce less stable radicals upon dissociation. In the image, the cyclohexyl bromine bond likely has a higher bond-dissociation energy because the resulting radical is less stable compared to the allylic radical, which is resonance-stabilized.
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04:09How to calculate enthalpy using bond dissociation energies.
Resonance Stabilization
Resonance stabilization occurs when a radical can delocalize its unpaired electron over multiple atoms, increasing stability. This is common in allylic positions, where the radical can be spread across a conjugated system. In the image, the allylic radical formed from the second structure is resonance-stabilized, making it more stable than the cyclohexyl radical, which lacks such delocalization.
Video consigliato:
03:43The radical stability trend.
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Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.
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