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The naturally occuring molecule a-terpineol is biosynthesized by a route that includes the following step. Show the mechanism for this step by drawing curved arrows to indicate the flow of electrons. Arrow-pushing Instructions H3C + >XT CH3 H CH3 H3C H3C :0-H CH3

The naturally occuring molecule a-terpineol is biosynthesized by a route that includes the following step. Show the mechanism for this step by drawing curved arrows to indicate the flow of electrons. Arrow-pushing Instructions H3C + >XT CH3 H CH3 H3C H3C :0-H CH3

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
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The naturally occurring molecule α-terpineol is biosynthesized by a route that includes the step illustrated above. The task is to show the mechanism for this step by drawing curved arrows to indicate the flow of electrons. **Diagram Explanation:** - **Reactant Structure (Left):** - The reactant comprises a cyclohexene ring with a methyl group (CH₃) attached to the upper right carbon. - A secondary carbocation (C⁺) is present at a tertiary carbon with two methyl groups and a hydrogen bonded to it. - An hydroxyl group (OH) with two lone pairs is present at a primary carbon. - **Product Structure (Right):** - The cyclohexene ring remains with a methyl group attached to the same position. - The secondary carbocation is now stabilized by the addition of the hydroxyl group, forming an oxonium ion (O⁺), with one lone pair and a positive charge stabilized by hydrogen bonding. **Arrow-pushing Instructions:** The arrow-pushing mechanism should involve: - Movement of electron pairs from the lone pairs on the oxygen atom towards the carbocation to form the C-O bond. This transformation highlights the nucleophilic attack of the hydroxyl group on the carbocation, leading to the formation of an intermediate oxonium ion.
Transcribed Image Text:The naturally occurring molecule α-terpineol is biosynthesized by a route that includes the step illustrated above. The task is to show the mechanism for this step by drawing curved arrows to indicate the flow of electrons. **Diagram Explanation:** - **Reactant Structure (Left):** - The reactant comprises a cyclohexene ring with a methyl group (CH₃) attached to the upper right carbon. - A secondary carbocation (C⁺) is present at a tertiary carbon with two methyl groups and a hydrogen bonded to it. - An hydroxyl group (OH) with two lone pairs is present at a primary carbon. - **Product Structure (Right):** - The cyclohexene ring remains with a methyl group attached to the same position. - The secondary carbocation is now stabilized by the addition of the hydroxyl group, forming an oxonium ion (O⁺), with one lone pair and a positive charge stabilized by hydrogen bonding. **Arrow-pushing Instructions:** The arrow-pushing mechanism should involve: - Movement of electron pairs from the lone pairs on the oxygen atom towards the carbocation to form the C-O bond. This transformation highlights the nucleophilic attack of the hydroxyl group on the carbocation, leading to the formation of an intermediate oxonium ion.
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