Alcohols, Ethers, and Epoxides PDF
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Loyola Marymount University
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Summary
This document provides a summary of substitution and elimination reactions of alcohols, ethers and epoxides. It covers topics such as SN1, SN2 reactions, and oxidation reactions. The document is a study guide, not an exam paper.
Full Transcript
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