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CH3 HCI →XT CH3 LOH CI CH3 H Epoxides are cleaved by acid as are other ethers, but milder conditions are sufficient due to ring strain. The mechanism of acid-catalyzed epoxide opening is complex. They seem to be neither purely SN1 nor SN2, but instead to be midway between these two extremes and to have characteristics of both mechanisms. When both epoxide carbon atoms are either primary or secondary, attack of the nucleophile occurs primarily at the less substituted site, an SN2-like result. On the other hand, when one of the epoxide carbons is tertiary nucleophilic attack occurs primarily at the more substituted site, an SN1-like result. OH Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions AN CI CH3 OH

CH3 HCI →XT CH3 LOH CI CH3 H Epoxides are cleaved by acid as are other ethers, but milder conditions are sufficient due to ring strain. The mechanism of acid-catalyzed epoxide opening is complex. They seem to be neither purely SN1 nor SN2, but instead to be midway between these two extremes and to have characteristics of both mechanisms. When both epoxide carbon atoms are either primary or secondary, attack of the nucleophile occurs primarily at the less substituted site, an SN2-like result. On the other hand, when one of the epoxide carbons is tertiary nucleophilic attack occurs primarily at the more substituted site, an SN1-like result. OH Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions AN CI CH3 OH

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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CH3 CH3 ÓH O H Epoxides are cleaved by acid as are other ethers, but milder conditions are sufficient due to ring strain. The mechanism of acid-catalyzed epoxide opening is complex. They seem to be neither purely SN1 nor SN2, but instead to be midway between these two extremes and to have characteristics of both mechanisms. When both epoxide carbon atoms are either primary or secondary, attack of the nucleophile occurs primarily at the less substituted site, an SN2-like result. On the other hand, when one of the epoxide carbons is tertiary nucleophilic attack occurs primarily at the more substituted site, an SN1-like result. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions HCI X' CH3 :ci: OH CH3 OH
Transcribed Image Text:CH3 CH3 ÓH O H Epoxides are cleaved by acid as are other ethers, but milder conditions are sufficient due to ring strain. The mechanism of acid-catalyzed epoxide opening is complex. They seem to be neither purely SN1 nor SN2, but instead to be midway between these two extremes and to have characteristics of both mechanisms. When both epoxide carbon atoms are either primary or secondary, attack of the nucleophile occurs primarily at the less substituted site, an SN2-like result. On the other hand, when one of the epoxide carbons is tertiary nucleophilic attack occurs primarily at the more substituted site, an SN1-like result. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions HCI X' CH3 :ci: OH CH3 OH
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