Domanda del libro di testo
In the following allylic radicals, identify the carbon where the new C― Br bond is most likely to form in the second propagation step.
(c)
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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 32c
Mullins 1st EditionCh. 11 - Properties and Synthesis of Alkyl Halides: Radical ReactionsProblema 32cCapitolo 10, Problema 32c
Predict the products of the following allylic halogenation reactions.
(c) 
Guida verificata passo dopo passo1
Identify the allylic position in the given molecule. The allylic position is the carbon atom adjacent to a carbon-carbon double bond.
Determine the halogen used in the reaction. Allylic halogenation typically involves chlorine (Cl2) or bromine (Br2) in the presence of a radical initiator like N-bromosuccinimide (NBS) for bromination.
Understand the mechanism: Allylic halogenation proceeds via a radical mechanism. The reaction begins with the formation of a radical at the allylic position.
Consider resonance stabilization: The allylic radical can be stabilized by resonance, which means the radical can be delocalized over the π system. Draw all possible resonance structures to identify potential sites for halogenation.
Predict the products: The halogen will add to the allylic position, and due to resonance, multiple products may form. Identify all possible products by considering each resonance structure and where the halogen can add.
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Allylic Halogenation
Allylic halogenation is a reaction where a halogen atom is introduced at the allylic position of an alkene. This position is adjacent to the double bond, and the reaction typically involves the use of N-bromosuccinimide (NBS) in the presence of light or heat to generate radicals. The process is selective for the allylic position due to the stability of the allylic radical intermediate.
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06:15
The general mechanism of Allylic Halogenation.
Radical Mechanism
The radical mechanism is a chain reaction involving initiation, propagation, and termination steps. In allylic halogenation, the initiation step generates radicals, often through the homolytic cleavage of a halogen molecule. Propagation involves the abstraction of a hydrogen atom from the allylic position, forming a stable allylic radical, which then reacts with a halogen molecule to form the halogenated product and regenerate the radical.
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03:28The mechanism of Radical Polymerization.
Stability of Allylic Radicals
Allylic radicals are more stable than typical alkyl radicals due to resonance stabilization. The unpaired electron in an allylic radical can be delocalized over the π system of the adjacent double bond, distributing the radical character over multiple atoms. This delocalization lowers the energy of the radical, making allylic positions more reactive in radical halogenation reactions.
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03:43The radical stability trend.
Pratica correlata
Domanda del libro di testo
The fact that allylic halogenation results in formation of the most stable alkene suggests that it is under thermodynamic control. Thus, the second propagation step must be reversible. Suggest an arrow-pushing mechanism by which the less stable allylic halide might equilibrate to the more stable allylic halide.
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Domanda del libro di testo
In the following allylic radicals, identify the carbon where the new C― Br bond is most likely to form in the second propagation step.
(b)
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Domanda del libro di testo
(a) Using bond-dissociation energies (Table 5.6), which of the indicated bonds should break most easily?
(b) How does that help you explain the results shown in Figure 11.40?
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Domanda del libro di testo
Predict the products of the following allylic halogenation reactions.
(d)
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Domanda del libro di testo
Predict the products of the following allylic halogenation reactions.
(a)
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