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H3C Arrow-pushing Instructions NOC XT H CH3 CH3 epi-Aristolochene, a hydrocarbon found in both pepper and tobacco, is biosynthesized in several steps. Propose a mechanism, using curved arrows to show the movement of electrons, for the step shown below. CH3 CH3 car-chy + H

H3C Arrow-pushing Instructions NOC XT H CH3 CH3 epi-Aristolochene, a hydrocarbon found in both pepper and tobacco, is biosynthesized in several steps. Propose a mechanism, using curved arrows to show the movement of electrons, for the step shown below. CH3 CH3 car-chy + H

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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### Synthesis of epi-Aristolochene **Introduction:** epi-Aristolochene is a hydrocarbon commonly found in plants such as pepper and tobacco. It is biosynthesized through a series of chemical reactions involving several steps. This section aims to illustrate one of these key steps in the synthesis process, highlighting the movement of electrons with a proposed reaction mechanism. **Chemical Reaction:** The image depicts a structural transformation involving a cyclic hydrocarbon. - **Starting Material:** - The left structure shows a cyclic hydrocarbon with an isopropyl group and a methyl group attached. There's a double bond in the ring and an additional unsaturation outside the ring. - **Product:** - The right structure represents a rearranged cyclic hydrocarbon where the configurations of certain substituents have changed positions, including the shift of a positive charge (a carbocation). **Mechanism Overview:** 1. **Arrow-pushing Instructions:** - Arrow-pushing is a technique used to illustrate the movement of electrons during a chemical reaction. The curved arrows indicate the flow of electron pairs, which is crucial for illustrating how the transformation occurs between the reactant and product. 2. **Detailed Explanation:** - In the first step, an arrow originates from the double bond, suggesting the formation of a carbocation intermediate. - The rearrangement leads to a new positioning of groups around the cyclic framework, reflective of the new carbocation location in the product structure. ### Conclusion: Understanding the electron flow using arrow-pushing is essential in proposing a mechanism for the biosynthesis of epi-Aristolochene. This visual representation aids in grasping the reorganization occurring at the molecular level, providing insights into the intricacies of natural product synthesis.
Transcribed Image Text:### Synthesis of epi-Aristolochene **Introduction:** epi-Aristolochene is a hydrocarbon commonly found in plants such as pepper and tobacco. It is biosynthesized through a series of chemical reactions involving several steps. This section aims to illustrate one of these key steps in the synthesis process, highlighting the movement of electrons with a proposed reaction mechanism. **Chemical Reaction:** The image depicts a structural transformation involving a cyclic hydrocarbon. - **Starting Material:** - The left structure shows a cyclic hydrocarbon with an isopropyl group and a methyl group attached. There's a double bond in the ring and an additional unsaturation outside the ring. - **Product:** - The right structure represents a rearranged cyclic hydrocarbon where the configurations of certain substituents have changed positions, including the shift of a positive charge (a carbocation). **Mechanism Overview:** 1. **Arrow-pushing Instructions:** - Arrow-pushing is a technique used to illustrate the movement of electrons during a chemical reaction. The curved arrows indicate the flow of electron pairs, which is crucial for illustrating how the transformation occurs between the reactant and product. 2. **Detailed Explanation:** - In the first step, an arrow originates from the double bond, suggesting the formation of a carbocation intermediate. - The rearrangement leads to a new positioning of groups around the cyclic framework, reflective of the new carbocation location in the product structure. ### Conclusion: Understanding the electron flow using arrow-pushing is essential in proposing a mechanism for the biosynthesis of epi-Aristolochene. This visual representation aids in grasping the reorganization occurring at the molecular level, providing insights into the intricacies of natural product synthesis.
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