### Reaction Mechanism and Analysis of Epoxide Ring-Opening Reaction#### Reaction Overview:The epoxide starting material shown here is a synthetic derivative of the antimalarial drug artemisinin. When treated with hexafluoro-2-propanol and catalytic acid, it undergoes an epoxy ring-opening reaction for which the regiochemical outcome and stereochemical outcome are both opposite of what you might have expected. Explain these observations with a plausible mechanism.#### Reaction Diagram:1. **Starting Material**: - The molecule features an epoxide ring, which is a three-membered cyclic ether. - Key substituents include a methyl group, hydrogen atoms, and an adjacent furan ring derivative.2. **Reaction Conditions**: - Reacting with hexafluoro-2-propanol (F3C-OH) and an acid catalyst (H3O+).3. **Product**: - The epoxide ring is opened, forming a diol. - Addition of the hexafluoro group (CF3) groups to the molecule.#### Plausible Mechanism Explanation:1. **Protonation of Epoxide**: - The epoxide oxygen can be protonated by the catalytic acid (H3O+), increasing the electrophilicity of the carbon atoms in the epoxide ring.2. **Nucleophilic Attack by Hexafluoro-2-Propanol**: - Hexafluoro-2-propanol acts as a nucleophile, with its hydroxyl group attacking one of the carbon atoms of the protonated epoxide. - Due to steric and electronic factors, the nucleophilic attack occurs at the less hindered carbon atom of the epoxide ring.3. **Ring Opening**: - The nucleophilic attack leads to the opening of the three-membered epoxide ring, resulting in the formation of a new carbon-oxygen single bond.4. **Regio- and Stereoselectivity**: - In this reaction, both the regiochemical and stereochemical outcomes are unexpected. - The regioselectivity implies that the nucleophile attacks a specific carbon atom of the epoxide ring, leading to the formation of a specific major product. - The stereoselectivity indicates that the spatial arrangement of the substituents in the product is different from what might be typically anticipated in a standard ring-opening reaction.This

Synthetic derivative of antimalarial drug artemisinin.

The epoxide starting material shown here is a synthetic derivative of the antimalarial drug artemisinin. When treated with hexafluoro-2-propanol and catalytic acid, it undergoes an epoxy ring-opening reaction for which the regiochemical outcome and stereochemical outcome are both opposite of what you might have expected. Explain these observations with a plausible mechanism. F3C H, -OH H, F3C HO- CF3 [H3O*] CF3

The epoxide starting material shown here is a synthetic derivative of the antimalarial drug artemisinin. When treated with hexafluoro-2-propanol and catalytic acid, it undergoes an epoxy ring-opening reaction for which the regiochemical outcome and stereochemical outcome are both opposite of what you might have expected. Explain these observations with a plausible mechanism. F3C H, -OH H, F3C HO- CF3 [H3O*] CF3

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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