Textbook Question
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 II: Oxidation and Reduction
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
Chapter 8, Problem 9
(••) Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br₂, H₂O(h)
Verified step by step guidance1
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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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
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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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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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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Related Practice
Textbook Question
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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Textbook Question
In contrast to the addition of Br₂ the addition of HBr [Section 8.3] is not stereospecific. Why?
Textbook Question
In which of the two steps in the alkene halogenation mechanism does a redox reaction occur?
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Textbook Question
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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Textbook Question
Provide an arrow-pushing mechanism that rationalizes the stereospecific formation of each dihalide in Assessment 9.6.
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