Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (x) D2, Pd/C.
(h)
1
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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 45h(i)
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (i) Br2
(h) 
Verified step by step guidance1
Step 1: Recognize the type of reaction. The reaction involves an alkene and bromine (Br₂), which is a halogenation reaction. This reaction typically proceeds via an electrophilic addition mechanism.
Step 2: Understand the mechanism. When Br₂ reacts with an alkene, the π-electrons of the double bond attack one of the bromine atoms, forming a cyclic bromonium ion intermediate. This intermediate is positively charged and highly reactive.
Step 3: Determine the nucleophilic attack. The bromide ion (Br⁻), which is generated when Br₂ splits, attacks the more substituted carbon of the bromonium ion (if applicable, based on Markovnikov's rule). This results in the anti-addition of bromine atoms across the double bond.
Step 4: Predict the stereochemistry. Since the bromonium ion intermediate is cyclic, the attack by the bromide ion occurs from the opposite side of the ring, leading to anti-addition. This means the two bromine atoms will be added to opposite faces of the former double bond.
Step 5: Draw the product(s). The final product will be a vicinal dibromide (two bromine atoms attached to adjacent carbons). If the starting alkene is symmetrical, a single product will form. If the alkene is asymmetrical, consider the possibility of stereoisomers (e.g., enantiomers or diastereomers).
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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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Bromination of Alkenes
Bromination is a specific type of electrophilic addition where bromine (Br₂) adds across the double bond of an alkene. This reaction typically results in the formation of vicinal dibromides, where bromine atoms are added to adjacent carbon atoms. The stereochemistry of the product can vary, leading to both anti and syn addition products.
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Stereochemistry of Addition Reactions
Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the bromination of alkenes, the addition of bromine can lead to different stereoisomers, such as enantiomers or diastereomers, depending on whether the addition occurs from the same or opposite sides of the double bond, influencing the final product's configuration.
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Related Practice
Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (ii) Cl2
(h)
6
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Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (x) D2 , Pd/C.
(k)
Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iv) Cl2, CH3OH
(k)
Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (viii) 1. O3 2. CH3SCH3
(h)
Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br2, H2O
(k)
4
views