Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (i) Br2
(h)
2
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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 45k(x)
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (x) D2 , Pd/C.
(k) 
Verified step by step guidance1
Identify the type of reaction: The reaction involves an alkene reacting with deuterium (D₂) in the presence of a palladium on carbon (Pd/C) catalyst. This is a catalytic hydrogenation reaction, where the double bond in the alkene is reduced to a single bond by the addition of deuterium atoms.
Understand the mechanism: In catalytic hydrogenation, the alkene π-bond interacts with the surface of the Pd/C catalyst, allowing the D₂ molecule to dissociate into two D atoms. These D atoms are then added to the carbon atoms of the double bond in a syn-addition manner (both deuterium atoms add to the same face of the alkene).
Determine the product: The double bond in the alkene is replaced by a single bond, and each carbon atom of the former double bond gains one deuterium atom. The stereochemistry of the product will depend on the starting alkene's structure (e.g., cis or trans).
Consider regioselectivity and stereoselectivity: Since this is a simple addition of deuterium, there is no regioselectivity to consider. However, the syn-addition nature of the reaction means that the stereochemistry of the product will reflect this (e.g., if the alkene is cyclic, the deuterium atoms will add to the same face of the ring).
Write the product structure: Replace the double bond in the alkene with a single bond, and add one deuterium atom to each carbon of the former double bond. Ensure the stereochemistry is consistent with syn-addition if applicable.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alkene Hydrogenation
Alkene hydrogenation is a chemical reaction where hydrogen (H₂) is added across the double bond of an alkene, converting it into an alkane. This process typically requires a catalyst, such as palladium on carbon (Pd/C), which facilitates the reaction by providing a surface for the alkene and hydrogen to interact. The result is a saturated hydrocarbon, which is generally more stable than the original alkene.
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The definition of hydrogenation.
Role of Catalysts
Catalysts are substances that increase the rate of a chemical reaction without being consumed in the process. In the context of alkene hydrogenation, palladium on carbon (Pd/C) serves as a catalyst that lowers the activation energy required for the reaction to occur. This allows the reaction to proceed more efficiently and at lower temperatures than would otherwise be necessary.
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Stereochemistry of Hydrogenation
Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. During hydrogenation of alkenes, the addition of hydrogen can lead to different stereoisomers, depending on the orientation of the hydrogen atoms added. In the case of symmetrical alkenes, the product is typically a single alkane, but for unsymmetrical alkenes, the stereochemistry can lead to the formation of cis and trans isomers, which are important in determining the properties of the resulting compound.
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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: (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
(k)
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
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Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (ii) Cl2
(k)
2
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Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vi) 1. OsO4 2. NaHSO3
(k)
3
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