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Give the major organic product of the following reactions. b) a CI + Br Br Br Diels-Alder Diels-Alder Diels-Alder CH₂OH NaSH

Give the major organic product of the following reactions. b) a CI + Br Br Br Diels-Alder Diels-Alder Diels-Alder CH₂OH NaSH

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**Title: Understanding Diels-Alder Reactions and Related Transformations** --- **Objective:** Identify the major organic product of the given reactions using the Diels-Alder approach and related conditions. --- **Reactions:** **a) Diels-Alder Reaction** - **Reactants:** - 1,3-butadiene (CH₂=CH-CH=CH₂) - 1,2-dibromoethene (BrCH=CHBr) - **Conditions:** - The Diels-Alder reaction typically proceeds via concerted cycloaddition. **b) Diels-Alder Reaction** - **Reactants:** - Cyclopentadiene - Methyl vinyl ketone (CH₂=CHC(O)CH₃) - **Conditions:** - Formation of a cyclohexene with ketone functionality in the newly formed ring. **c) Diels-Alder Reaction** - **Reactants:** - Cyclopentadiene - Fumaronitrile (NCCH=CHCN) - **Conditions:** - Reaction forming a bicyclic compound with cyano groups in the newly formed ring. **d) Reaction with Methanol (CH₃OH)** - **Reactants:** - Alkyl bromide attached to a cyclohexane - **Conditions:** - Involves the substitution of bromine by a methoxy group under neutral to basic conditions. **e) Nucleophilic Substitution with Sodium Hydrogen Sulfide (NaSH)** - **Reactants:** - Chlorobutane - **Conditions:** - Replacement of chlorine by a thiol group resulting in butanethiol. --- **Diagram Explanation:** No specific diagrams are included, but if these were illustrated, each reaction would start from the reactants leading to a cyclic or substitution product through a series of arrows depicting the mechanistic pathway. **Conclusion:** The Diels-Alder reactions are a classic example of concerted cycloaddition commonly used in the construction of six-membered rings. Other transformations such as nucleophilic substitution highlight the versatility of organic synthesis in modifying functional groups. Understanding these reactions provides a solid foundation for further exploration in synthetic chemistry.
Transcribed Image Text:**Title: Understanding Diels-Alder Reactions and Related Transformations** --- **Objective:** Identify the major organic product of the given reactions using the Diels-Alder approach and related conditions. --- **Reactions:** **a) Diels-Alder Reaction** - **Reactants:** - 1,3-butadiene (CH₂=CH-CH=CH₂) - 1,2-dibromoethene (BrCH=CHBr) - **Conditions:** - The Diels-Alder reaction typically proceeds via concerted cycloaddition. **b) Diels-Alder Reaction** - **Reactants:** - Cyclopentadiene - Methyl vinyl ketone (CH₂=CHC(O)CH₃) - **Conditions:** - Formation of a cyclohexene with ketone functionality in the newly formed ring. **c) Diels-Alder Reaction** - **Reactants:** - Cyclopentadiene - Fumaronitrile (NCCH=CHCN) - **Conditions:** - Reaction forming a bicyclic compound with cyano groups in the newly formed ring. **d) Reaction with Methanol (CH₃OH)** - **Reactants:** - Alkyl bromide attached to a cyclohexane - **Conditions:** - Involves the substitution of bromine by a methoxy group under neutral to basic conditions. **e) Nucleophilic Substitution with Sodium Hydrogen Sulfide (NaSH)** - **Reactants:** - Chlorobutane - **Conditions:** - Replacement of chlorine by a thiol group resulting in butanethiol. --- **Diagram Explanation:** No specific diagrams are included, but if these were illustrated, each reaction would start from the reactants leading to a cyclic or substitution product through a series of arrows depicting the mechanistic pathway. **Conclusion:** The Diels-Alder reactions are a classic example of concerted cycloaddition commonly used in the construction of six-membered rings. Other transformations such as nucleophilic substitution highlight the versatility of organic synthesis in modifying functional groups. Understanding these reactions provides a solid foundation for further exploration in synthetic chemistry.
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