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Propose a reasonable mechanism for the following reactions: H+, H₂O OH HBr OH isto T

Propose a reasonable mechanism for the following reactions: H+, H₂O OH HBr OH isto T

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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### Question 1: Propose a reasonable mechanism for the following reactions: 1. **First Reaction:** **Reactants:** - Cyclohexene (a six-membered ring with one double bond) - Acid (H⁺) and water (H₂O) **Products:** - Cyclohexanol (a six-membered ring with one hydroxyl group, OH, attached) **Description:** - This reaction is an acid-catalyzed hydration of an alkene. The reaction mechanism likely involves the formation of a carbocation intermediate after the addition of H⁺ to the double bond of cyclohexene. Water then attacks the carbocation, followed by deprotonation to yield cyclohexanol. 2. **Second Reaction:** **Reactants:** - 5-Hexen-1-ol (an alcohol with an alkene, six-carbon chain with a double bond between the fifth and sixth carbon and a hydroxyl group on the first carbon) - Hydrogen bromide (HBr) **Products:** - Tetrahydropyran (a six-membered ring with an oxygen atom, also known as oxane, with a methyl group attached to the second carbon) **Description:** - The mechanism of this reaction likely involves the initial protonation of the hydroxyl group of 5-hexen-1-ol by the HBr, forming a good leaving group. This is followed by the formation of a carbocation, which undergoes an intramolecular ring closure to form the tetrahydropyran ring structure. Note: These reactions illustrate typical mechanisms in organic chemistry involving the hydration of alkenes and intramolecular cyclization reactions.
Transcribed Image Text:### Question 1: Propose a reasonable mechanism for the following reactions: 1. **First Reaction:** **Reactants:** - Cyclohexene (a six-membered ring with one double bond) - Acid (H⁺) and water (H₂O) **Products:** - Cyclohexanol (a six-membered ring with one hydroxyl group, OH, attached) **Description:** - This reaction is an acid-catalyzed hydration of an alkene. The reaction mechanism likely involves the formation of a carbocation intermediate after the addition of H⁺ to the double bond of cyclohexene. Water then attacks the carbocation, followed by deprotonation to yield cyclohexanol. 2. **Second Reaction:** **Reactants:** - 5-Hexen-1-ol (an alcohol with an alkene, six-carbon chain with a double bond between the fifth and sixth carbon and a hydroxyl group on the first carbon) - Hydrogen bromide (HBr) **Products:** - Tetrahydropyran (a six-membered ring with an oxygen atom, also known as oxane, with a methyl group attached to the second carbon) **Description:** - The mechanism of this reaction likely involves the initial protonation of the hydroxyl group of 5-hexen-1-ol by the HBr, forming a good leaving group. This is followed by the formation of a carbocation, which undergoes an intramolecular ring closure to form the tetrahydropyran ring structure. Note: These reactions illustrate typical mechanisms in organic chemistry involving the hydration of alkenes and intramolecular cyclization reactions.
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