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)
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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 45f(i,ii)
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (i) Br2 (ii) Cl2
(f) 
Verified step by step guidance1
Identify the type of reaction: The reaction involves halogens (Br₂ and Cl₂) reacting with alkenes. This is an electrophilic addition reaction where the halogen molecules add across the double bond of the alkene.
Understand the mechanism: The π-electrons of the alkene double bond attack the halogen molecule (e.g., Br₂), forming a cyclic halonium ion intermediate. This intermediate is then attacked by a halide ion (e.g., Br⁻), leading to the formation of a vicinal dihalide (halogens on adjacent carbons).
Analyze the stereochemistry: The addition of halogens to alkenes is anti-addition, meaning the two halogen atoms will add to opposite sides of the double bond, resulting in a trans product.
Apply the reaction conditions: For (i) Br₂, the product will be a vicinal dibromide. For (ii) Cl₂, the product will be a vicinal dichloride. Ensure to consider the specific structure of the alkene provided in the image to determine the exact placement of the halogens.
Draw the product(s): Based on the structure of the starting alkene, draw the products for each reaction, ensuring to show the correct stereochemistry (anti-addition) and placement of the halogen atoms on the carbon atoms originally involved in 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 Reactions
Electrophilic addition reactions are a fundamental type of reaction for alkenes, where an electrophile reacts with the double bond of the alkene. This process involves the formation of a carbocation intermediate, which is then attacked by a nucleophile. Understanding this mechanism is crucial for predicting the products when alkenes react with halogens like Br₂ and Cl₂.
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Features of Addition Mechanisms.
Halogenation of Alkenes
Halogenation refers to the addition of halogen molecules (such as Br₂ or Cl₂) to alkenes, resulting in the formation of vicinal dihalides. This reaction typically proceeds via a cyclic halonium ion intermediate, which influences the stereochemistry of the product. Recognizing the stereochemical outcomes is essential for accurately predicting the products of these reactions.
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Regioselectivity
Regioselectivity is the preference of a chemical reaction to yield one structural isomer over others when multiple products are possible. In the context of alkene halogenation, regioselectivity can be influenced by the stability of the carbocation intermediate formed during the reaction. Understanding regioselectivity helps in predicting which halogen will add to which carbon of the alkene, leading to the correct product structure.
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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: (i) Br2
(h)
1328
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Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (ix) H2, Pd/C;
(h)
1169
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Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br2, H2O ; (iv) Cl2, CH3OH
(f)
786
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Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. (viii) 1. O3 2. CH3SCH3
(f)
742
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Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA; (vi) 1. OsO4 2. NaHSO3
(f)
891
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