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Unformatted text preview: Ethers/Epoxides 1 Copyright, Arizona State University Copyright, Arizona State University Ethers/Epoxides Reactions With Brnsted Acids/Bases 1 Terminology/Properties R O R Symmetric R O R' Asymmetric O Epoxide R O R' Tetrahedral ~105 Generally unreactive although Epoxides are an exception Good Organic Solvents 2 Nomenclature Named as substituents (like halides), lowest priority Substituent is named as the ALKOXY is equivalent to ALKYL, i.e. Me is methyl, thus, -OMe is methoxy etc. R O R' O More complex side is the main chain A l k o x y substituent (4S)-tert-butoxycyclohexene 1 2 3 4 More complex side - Alkene substituent O ethoxy substituent 1-ethoxybutane 1 2 3 4 Some Common Ethers and Common Names O diethyl ether O O O O ethylene oxide (oxirane) tetrahydrofuran (THF) oxetane tetrahydropyran 3 Preparation of Ethers 3.1 Williamson Ether Synthesis (SN2 Reaction) This is just an SN2 reaction, but we will analyze it using retrosynthetic analysis Retrosynthetic strategy O R' synthons R R O R' "put" negative charge on the oxygen and a leaving group on the carbon O R' R O R' X synthetic equivalents : reagents R Na alkoxide anion Ethers/Epoxides 2 Copyright, Arizona State University Copyright, Arizona State University Ether/Epoxide PROBLEMS Ether/Epoxide Nomenclature In each case, give the IUPAC name for the provided structure (ignore stereochemistry unless specified) 1 (easier) O Answer Correct Y / N 2 (easier) HO O Br Answer Correct Y / N 3 (standard) MeO OMe CH OMe Answer Correct Y / N 4 (standard) O O Answer Correct Y / N 5 (standard) OCH 3 H 3 CO Answer Correct Y / N 6 (standard) O C CH 3 CH 3 CH 3 Answer Correct Y / N 7 (standard) O CH 2 CH 2 CH 3 Answer Correct Y / N 8 (standard) CH CH 3 CH 3 CH 2 O CH 2 CH 3 Answer Correct Y / N 9 (standard) CH 2 O CH 2 O CH 3 CH 3 Answer Correct Y / N 10 (standard) CH CH 3 CH 3 CH 2 O CH 2 CH 2 CH 3 Answer Correct Y / N 11 (standard) O Answer Correct Y / N 12 (standard) O H OCH 3 H H 3 C Answer Correct Y / N Doing problems is the only way that you will learn organic chemistry. You should do problems in the notes, from the textbook and from problem sets. It is CRITICAL that you keep track of what you know and what you don't know. Each notes problem has a "Correct Y / N" box. When you are PROPERLY CONVINCED that you can do a problem, circle "Y", if you can't do the problem circle "N". Keep coming back to those problems with the circled "N", until you can circle the "Y"....
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