Domanda del libro di testo
Calculate the atom economy for the reactions shown. In each, what happens to the percentage of material that is not incorporated into the major product?
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Ch. 9 - Alkenes 2: Oxidation and Reduction
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
Capitolo 8, Problema 9
(••) Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br₂, H₂O (h)
Guida verificata passo dopo passo1
Identify the type of reaction: The reaction of an alkene with Br₂ in the presence of H₂O is a halohydrin formation reaction.
Understand the mechanism: The reaction proceeds via the formation of a bromonium ion intermediate, which is then attacked by water.
Determine regioselectivity: The water molecule will attack the more substituted carbon of the bromonium ion, leading to Markovnikov addition.
Consider stereochemistry: The addition of Br and OH will be anti, meaning they will add to opposite sides of the double bond.
Predict the product: The final product will be a halohydrin, with a bromine atom and a hydroxyl group added across the double bond.
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Concetti chiave
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Electrophilic Addition
Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile reacts with a nucleophile, typically involving alkenes. In the case of alkenes reacting with Br₂, the double bond acts as a nucleophile, attacking the electrophilic bromine molecule, leading to the formation of a cyclic bromonium ion intermediate.
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1,2 vs 1,4 Addition
Bromohydrin Formation
Bromohydrin formation occurs when an alkene reacts with bromine in the presence of water. The bromonium ion intermediate is attacked by water, leading to the formation of a bromohydrin, which is a compound containing both a bromine atom and a hydroxyl group (-OH) on adjacent carbon atoms, resulting in a vicinal dibromide.
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02:26Formation of Enolates
Regioselectivity
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple products are possible. In the reaction of alkenes with Br₂ and H₂O, the regioselectivity is influenced by the stability of the carbocation intermediates formed during the reaction, often leading to the more substituted alcohol being produced as the major product.
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05:09Heck Reaction
Pratica correlata
Domanda del libro di testo
Predict the product(s) of each of the following reactions, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers.
(a)
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Domanda del libro di testo
In contrast to the addition of Br₂ the addition of HBr [Section 8.3] is not stereospecific. Why?
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Domanda del libro di testo
In which of the two steps in the alkene halogenation mechanism does a redox reaction occur?
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Domanda del libro di testo
Provide arrow-pushing mechanisms for Assessments 9.10(b) and 9.10(c) that rationalize the regioselective and stereospecific formation of each halohydrin.
(b)
(c)
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Domanda del libro di testo
Provide an arrow-pushing mechanism that rationalizes the stereospecific formation of each dihalide in Assessment 9.6.
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