Alcohols, Ethers, and Epoxides PDF
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Loyola Marymount University
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Summary
This document covers the substitution and elimination reactions of alcohols, ethers, and epoxides. It details the different reaction mechanisms, including SN1 and SN2, and provides examples of oxidizing alcohols. This is potentially from a chemistry textbook or study notes.
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Alcohols, Ethers, and Epoxides 9/8/24, 3:26 AM Platform | Study Fetch Substitution and Elimination of Alcohols Substitution Reactions with H-X Proceeds via SN2 for 1° alcohols and methanol Proceeds via SN1 for 3° and 2° a...
Alcohols, Ethers, and Epoxides 9/8/24, 3:26 AM Platform | Study Fetch Substitution and Elimination of Alcohols Substitution Reactions with H-X Proceeds via SN2 for 1° alcohols and methanol Proceeds via SN1 for 3° and 2° alcohols Reactions with PBr3 (1° and 2° alcohols) Reactions with SOCl2 (1° and 2° alcohols) Conversion to sulfonate esters (tosylates and mesylates) Dehydration with H2SO4 or H3PO4 E2 for 1° alcohols E1 for 3° and 2° alcohols (Bootcamp.com 50) Oxidizing Alcohols Chromium Reagents Oxidize 1° alcohols and aldehydes to carboxylic acids Oxidize 2° alcohols into ketones PCC Oxidation Oxidizes 1° alcohols to aldehydes and 2° alcohols to ketones Swern Oxidation Does the same thing as PCC, oxidizes 1° alcohols to aldehydes and 2° alcohols to ketones (Bootcamp.com 51) Reactions of Ethers Williamson Ether Synthesis (SN2) Adding H-X to Ethers The reaction will proceed through an SN1 mechanism if you have a secondary or tertiary carbon group. If not, it'll go SN2 and attack the least sterically hindered side. (Bootcamp.com 52) Reactions of Epoxides Epoxide Synthesis Ring Opening of Epoxides https://www.studyfetch.com/platform/studyset/65f316b6d2ca571ed94337bc/material/66db06b3248edfd9457d94f5/document 1/2 Base-Catalyzed (Nucleophile attacks less substituted side) 9/8/24, 3:26 AM Platform | Study Fetch Acid-Catalyzed (Nucleophile attacks the more substituted side) https://www.studyfetch.com/platform/studyset/65f316b6d2ca571ed94337bc/material/66db06b3248edfd9457d94f5/document 2/2