Domanda del libro di testo
Predict the product of the following benzylic bromination reactions.
(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
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Mullins 1st EditionCh. 11 - Properties and Synthesis of Alkyl Halides: Radical ReactionsProblema 63b
Mullins 1st EditionCh. 11 - Properties and Synthesis of Alkyl Halides: Radical ReactionsProblema 63bCapitolo 10, Problema 63b
Predict the product of the following benzylic bromination reactions.
(b) 
Guida verificata passo dopo passo1
Identify the type of reaction: This is a benzylic bromination reaction, which typically involves the substitution of a hydrogen atom at the benzylic position with a bromine atom.
Locate the benzylic position: The benzylic position is the carbon atom directly attached to the benzene ring. In this reaction, identify the carbon atom that is adjacent to the benzene ring.
Consider the mechanism: Benzylic bromination usually proceeds via a radical mechanism. The presence of a radical initiator, such as N-bromosuccinimide (NBS), facilitates the formation of a benzylic radical.
Predict the formation of the benzylic radical: The hydrogen atom at the benzylic position is abstracted, forming a benzylic radical. This radical is stabilized by resonance with the benzene ring.
Determine the final product: The benzylic radical reacts with bromine to form the brominated product. The bromine atom replaces the hydrogen atom at the benzylic position, resulting in the formation of the benzylic bromide.
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Benzylic Bromination
Benzylic bromination is a type of radical halogenation reaction where a bromine atom is introduced at the benzylic position, which is the carbon atom directly attached to a benzene ring. This reaction typically involves the use of N-bromosuccinimide (NBS) and a radical initiator, such as light or heat, to generate bromine radicals that selectively react with the benzylic hydrogen atoms.
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00:54
Mechanism of Allylic Bromination.
Radical Mechanism
Radical mechanisms involve the formation and reaction of radicals, which are species with unpaired electrons. In benzylic bromination, the reaction proceeds through a radical chain mechanism, starting with the generation of bromine radicals, followed by hydrogen abstraction from the benzylic position, and finally, the formation of the brominated product. Understanding the stability and reactivity of radicals is crucial for predicting the outcome of such reactions.
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03:28The mechanism of Radical Polymerization.
Benzylic Position Stability
The benzylic position is highly reactive due to the stability of the benzylic radical formed during the reaction. This stability arises from resonance, where the unpaired electron can be delocalized over the aromatic ring, making the benzylic radical more stable than other alkyl radicals. This enhanced stability is a key factor in the selectivity of benzylic bromination reactions, as it favors the formation of products at the benzylic position.
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Percorso guidato
2:46Reactions at Benzylic Positions Concept 2
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(a)
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