Textbook Question
When fumarate reacts with D2O in the presence of the enzyme fumarase, only one isomer of the product is formed, as shown here. Is the enzyme catalyzing a syn or an anti addition of D2O?
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Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 6 - The Reactions of Alkenes • The Stereochemistry of Addition ReactionsProblem 100
Bruice 8th EditionCh. 6 - The Reactions of Alkenes • The Stereochemistry of Addition ReactionsProblem 100Chapter 7, Problem 100
What stereoisomers are obtained when (S)-3-methyl-1-pentene reacts with Cl2?
Verified step by step guidance1
Identify the type of reaction: The reaction of (S)-3-methyl-1-pentene with Cl₂ is an electrophilic addition reaction, specifically a halogenation reaction. This involves the addition of two chlorine atoms across the double bond.
Determine the intermediate: The reaction proceeds via the formation of a cyclic chloronium ion intermediate. The double bond in (S)-3-methyl-1-pentene acts as a nucleophile and attacks one of the chlorine atoms, forming the cyclic intermediate and leaving a chloride ion (Cl⁻).
Analyze the stereochemistry of the intermediate: The cyclic chloronium ion is planar at the carbon atoms involved in the double bond, allowing the chloride ion to attack from either the top or bottom face of the molecule. This leads to the formation of stereoisomers.
Predict the products: The attack of the chloride ion on the cyclic intermediate results in the formation of a vicinal dihalide (a compound with two adjacent chlorine atoms). Since the attack can occur from either face, two stereoisomers are formed: one with the chlorines in a trans configuration and one with the chlorines in a cis configuration.
Conclude the stereoisomers: The final products are a pair of enantiomers (mirror-image stereoisomers) due to the chiral center at carbon-3. These enantiomers are formed because the original (S)-configuration at carbon-3 is retained or inverted depending on the face of attack by the chloride ion.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Stereoisomerism
Stereoisomerism refers to the phenomenon where compounds have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of those atoms. This can lead to different physical and chemical properties. In the case of alkenes, stereoisomers can arise from the restricted rotation around the double bond, resulting in cis and trans configurations.
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Electrophilic Addition Reactions
Electrophilic addition reactions are a fundamental type of reaction for alkenes, where an electrophile reacts with the double bond, leading to the formation of a more saturated compound. In the case of (S)-3-methyl-1-pentene reacting with Cl2, the chlorine molecules act as electrophiles, adding across the double bond and resulting in the formation of vicinal dihalides.
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Chirality and Enantiomers
Chirality is a property of a molecule that makes it non-superimposable on its mirror image, often due to the presence of a chiral center, typically a carbon atom bonded to four different substituents. When (S)-3-methyl-1-pentene reacts with Cl2, the formation of chiral products can lead to the generation of enantiomers, which are pairs of molecules that are mirror images of each other, impacting the overall stereochemistry of the reaction.
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Related Practice
Textbook Question
Propose a mechanism for the following reaction:
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Textbook Question
Which compound is hydrated more rapidly?
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Textbook Question
What hydrocarbon forms the following products after reaction first with ozone and then with dimethyl sulfide?
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Textbook Question
When the following compound is hydrated in the presence of acid, the unreacted alkene is found to have retained the deuterium atoms. What does this tell you about the mechanism for hydration?
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Textbook Question
Ozonolysis of an alkene, followed by treatment with dimethyl sulfide, forms the following product(s). Identify the alkene in each case.
a.
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