Textbook Question
Ozonolysis of an alkene, followed by treatment with dimethyl sulfide, forms the following product(s). Identify the alkene in each case.
b.
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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 101
Bruice 8th EditionCh. 6 - The Reactions of Alkenes • The Stereochemistry of Addition ReactionsProblem 101Chapter 7, Problem 101
Propose a mechanism for the following reaction:
Verified step by step guidance1
Step 1: Identify the reaction type. This is an acid-catalyzed hydration of an alkene. The alkene reacts with water in the presence of sulfuric acid (H₂SO₄) to form an alcohol.
Step 2: Protonation of the alkene. The sulfuric acid donates a proton (H⁺) to the double bond of the alkene, forming a carbocation intermediate. The more stable carbocation will form, so consider the rearrangement of the carbocation if necessary.
Step 3: Nucleophilic attack by water. The water molecule acts as a nucleophile and attacks the carbocation, forming an oxonium ion (a positively charged oxygen species).
Step 4: Deprotonation of the oxonium ion. A water molecule or another base removes a proton from the oxonium ion, resulting in the formation of the alcohol product.
Step 5: Analyze the product structure. The final product is a tertiary alcohol, indicating that the carbocation formed during the reaction underwent rearrangement to achieve maximum stability before the nucleophilic attack by water.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Reaction Mechanism
A reaction mechanism is a step-by-step description of how a chemical reaction occurs at the molecular level. It outlines the sequence of elementary steps, including bond breaking and formation, and the intermediates formed during the reaction. Understanding the mechanism helps predict the products and the conditions under which the reaction occurs.
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Nucleophiles and Electrophiles
Nucleophiles are species that donate an electron pair to form a chemical bond, while electrophiles are electron-deficient species that accept an electron pair. Identifying these species in a reaction is crucial for proposing a mechanism, as it determines how reactants interact and the direction of electron flow during the reaction.
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Transition States and Intermediates
Transition states are high-energy states that occur during the transformation of reactants to products, representing the point of maximum energy along the reaction pathway. Intermediates are species that are formed and consumed during the reaction but are not present in the final products. Understanding these concepts is essential for accurately depicting the mechanism and energy changes throughout the reaction.
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Related Practice
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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Textbook Question
What stereoisomers are obtained when (S)-3-methyl-1-pentene reacts with Cl2?
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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.
850
views