CH3 H HCI 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 complex. They seem to be neither purely SN1 nor SN2, but instead to be midw 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. C the other hand, when one of the epoxide carbons is tertiary nucleophilic attack occurs primarily at the more substituted site, an SN1-like result. H-CI OH Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions 20 →XT CH3 CH3 OH CI

CH3 H HCI 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 complex. They seem to be neither purely SN1 nor SN2, but instead to be midw 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. C the other hand, when one of the epoxide carbons is tertiary nucleophilic attack occurs primarily at the more substituted site, an SN1-like result. H-CI OH Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions 20 →XT CH3 CH3 OH CI

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter18: Ethers And Epoxides; Thiols And Sulfides

Section18.SE: Something Extra

Problem 36MP: Aldehydes and ketones undergo acid-catalyzed reaction with alcohols to yield hemiacetals, compounds...

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