Textbook Question
Based on the stability of the radicals produced, predict which bond in each pair would have the higher bond-dissociation energy.
(a)
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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 14
Mullins 1st EditionCh. 11 - Properties and Synthesis of Alkyl Halides: Radical ReactionsProblem 14Chapter 10, Problem 14
Provide a mechanism for the chlorination of cyclohexane. Be sure to include initiation, propagation, and three possible termination steps.
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Initiation: The chlorination of cyclohexane begins with the homolytic cleavage of the chlorine molecule (Cl₂) under the influence of heat or light. This results in the formation of two chlorine radicals. The reaction can be represented as: Cl₂ → 2Cl•.
Propagation Step 1: A chlorine radical abstracts a hydrogen atom from cyclohexane, forming hydrochloric acid (HCl) and a cyclohexyl radical. This step can be represented as: Cl• + C₆H₁₂ → HCl + C₆H₁₁•.
Propagation Step 2: The cyclohexyl radical reacts with another chlorine molecule to form chlorocyclohexane and regenerate a chlorine radical. This step can be represented as: C₆H₁₁• + Cl₂ → C₆H₁₁Cl + Cl•.
Termination Step 1: Two chlorine radicals can combine to form chlorine gas, effectively removing radicals from the reaction mixture. This step can be represented as: Cl• + Cl• → Cl₂.
Termination Step 2: A cyclohexyl radical can combine with a chlorine radical to form chlorocyclohexane, terminating the radical chain. This step can be represented as: C₆H₁₁• + Cl• → C₆H₁₁Cl.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Free Radical Halogenation
Free radical halogenation is a reaction mechanism where halogens, such as chlorine, react with alkanes to form alkyl halides. This process involves the generation of free radicals, which are highly reactive species with unpaired electrons. The mechanism consists of three main stages: initiation, propagation, and termination, each playing a crucial role in the overall reaction.
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Radical Chain Reaction Mechanism.
Initiation Step
The initiation step involves the formation of free radicals, typically through the homolytic cleavage of a chlorine molecule (Cl2) under heat or light. This generates two chlorine radicals, which are essential for starting the chlorination process. The presence of these radicals sets the stage for the subsequent propagation steps, where they will react with cyclohexane.
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Propagation and Termination Steps
Propagation steps involve the reaction of chlorine radicals with cyclohexane to form alkyl radicals, which can further react with chlorine molecules to produce alkyl halides and regenerate chlorine radicals. Termination steps occur when two radicals combine to form a stable product, effectively stopping the chain reaction. These steps are crucial for controlling the reaction and determining the final products.
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Related Practice
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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Textbook Question
Specify the conditions that would allow the synthesis of the 1° and 3° bromoalkanes from the same starting alkene.
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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
The most stable intermediate forms first. Explain this statement by showing a reaction coordinate diagram for the formation of a 3° carbocation over a 2° carbocation in the following alkene addition reaction.
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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)
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