Textbook Question
(••) Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br₂, H₂O(h)
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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 8
In which of the two steps in the alkene halogenation mechanism does a redox reaction occur?
Verified step by step guidance1
Step 1: Begin by understanding the alkene halogenation mechanism. This reaction involves two main steps: (1) the formation of a halonium ion intermediate and (2) the nucleophilic attack by the halide ion.
Step 2: Recall the definition of a redox reaction. A redox reaction involves the transfer of electrons, where one species is oxidized (loses electrons) and another is reduced (gains electrons).
Step 3: Analyze the first step of the mechanism. When the halogen molecule (e.g., Br₂ or Cl₂) approaches the alkene, the π-electrons of the alkene attack the halogen, forming a halonium ion. In this step, the halogen molecule is reduced as it gains electrons, and the alkene is oxidized as it loses electrons. This is a redox reaction.
Step 4: Examine the second step of the mechanism. The halide ion (e.g., Br⁻ or Cl⁻) attacks the halonium ion to open the ring and form the final dihalogenated product. This step does not involve a transfer of electrons in the sense of oxidation or reduction, so it is not a redox reaction.
Step 5: Conclude that the redox reaction occurs in the first step of the alkene halogenation mechanism, where the halogen molecule is reduced and the alkene is oxidized.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alkene Halogenation Mechanism
The alkene halogenation mechanism involves the addition of halogens (like Cl2 or Br2) to an alkene, resulting in a vicinal dihalide. This process typically occurs in two main steps: the formation of a cyclic halonium ion and the subsequent nucleophilic attack by a halide ion. Understanding this mechanism is crucial for identifying where redox reactions may take place.
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03:45
Halogenation Mechanism
Redox Reactions
Redox reactions involve the transfer of electrons between species, resulting in changes in oxidation states. In the context of alkene halogenation, the halogen molecule is reduced as it forms a halonium ion, while the alkene is oxidized. Recognizing these electron transfer processes is essential for pinpointing the steps in which redox reactions occur.
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06:02General Features of Redox
Oxidation States
Oxidation states are a way to keep track of electron transfer in chemical reactions. In the alkene halogenation mechanism, the oxidation state of the carbon atoms in the alkene changes as they bond with halogen atoms. Understanding how to assign and interpret oxidation states helps in identifying the specific steps where redox reactions happen.
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03:08Ground vs. Excited States
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.
(f)
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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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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?
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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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