Textbook Question
What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide?
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 92b
Bruice 8th EditionCh. 6 - The Reactions of Alkenes • The Stereochemistry of Addition ReactionsProblem 92bChapter 7, Problem 92b
Dichlorocarbene can also be generated by heating sodium trichloroacetate. Propose a mechanism for the reaction.
Verified step by step guidance1
Step 1: Begin by identifying the starting material, sodium trichloroacetate (NaO−CCl3). This compound contains a trichloromethyl group attached to a carboxylate functional group.
Step 2: Upon heating, the carboxylate group undergoes decarboxylation. This process involves the loss of carbon dioxide (CO2), which is facilitated by the thermal energy provided.
Step 3: The decarboxylation results in the formation of a trichloromethyl anion (CCl3−). This intermediate is highly unstable and undergoes further reaction.
Step 4: The trichloromethyl anion (CCl3−) eliminates a chloride ion (Cl−), leading to the generation of dichlorocarbene (:CCl2). Dichlorocarbene is a reactive intermediate with a divalent carbon atom and two lone pairs.
Step 5: The final products of the reaction are dichlorocarbene (:CCl2), carbon dioxide (CO2), and sodium chloride (NaCl). The mechanism highlights the thermal decomposition and rearrangement steps leading to the formation of these products.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Dichlorocarbene Generation
Dichlorocarbene (Br2C:) is a reactive intermediate formed during certain organic reactions. It can be generated from precursors like sodium trichloroacetate through thermal decomposition. The process involves the loss of carbon dioxide (CO2) and the formation of the dichlorocarbene species, which is crucial for various synthetic applications in organic chemistry.
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Thermal Decomposition
Thermal decomposition is a chemical reaction where a compound breaks down into simpler substances when heated. In the context of sodium trichloroacetate, heating induces the cleavage of bonds, leading to the release of CO2 and the formation of dichlorocarbene. Understanding this concept is essential for predicting the products of reactions involving heat.
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Mechanism of Reaction
A reaction mechanism describes the step-by-step sequence of elementary reactions by which overall chemical change occurs. For the generation of dichlorocarbene from sodium trichloroacetate, the mechanism involves bond breaking and formation, which can be illustrated through curved arrows in reaction diagrams. Analyzing the mechanism helps in understanding the stability and reactivity of intermediates.
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Related Practice
Textbook Question
The reaction of an alkene with diazomethane forms a cyclopropane ring. Propose a mechanism for the reaction. (Hint: It is a concerted reaction.)
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Textbook Question
What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide?
a.
703
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Textbook Question
A, a compound with molecular formula C6H10, contains three methylene units. A reacts with one equivalent of H2 over Pd/C to yield B. A reacts with aqueous acid to form a single product, C, and undergoes hydroboration/oxidation to form a pair of enantiomers, D and E. Ozonolysis of A followed by reaction with dimethyl sulfide forms F with molecular formula C6H10O2. Provide structures for A–F.
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Textbook Question
Two chemists at Dupont found that ICH2ZnI is better than diazomethane at converting a C=C bond to a cylcopropane ring. Propose a mechanism for the reaction, now known as the Simmons–Smith reaction in their honor.
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Textbook Question
What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide?
c.
753
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