Chapter 11: Alcohols, Ethers, Epoxides

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Presentation transcript:

Chapter 11: Alcohols, Ethers, Epoxides CH 11-1 Introduction & Nomenclature Nomenclature: alcohols only Synthesis of Alcohols (reviewed in Problem Set #1): -SN1 & SN2 (H2O & HO-, respectively) -acid-catalyzed alkene hydration Synthesis of Ethers (same as alcohol synthesis): -SN1 & SN2 (ROH or RO-, respectively) -acid-catalyzed ROH addition to alkenes Reactions of Alcohols: (a) acid/base (previous chapters) (b) H2O as a leaving group (Sub/Elim) -Dehydration to alkenes (E1, E2), Chapter 7 -Substitution to R-X (SN1, SN2) (c) ROH as a nucleophile (ether synthesis - SN2) Reactions of Epoxides – Stereospecific (SN1 or SN2)

Review of Organic Reactions & Mechanisms E1 & E2 Electrophilic addition SN1 SN2 SN1 SN2 (acid catalyzed) (acid cat.) Dehydration Electrophilic addn (hydration) acid/base exchange acid/base SN2

Alcohol Nomenclature Identify longest alkane carbon chain containing the hydroxyl functional group Drop the –e ending of the alkane and add –ol Numbering is fixed by location of the hydroxyl group (2S, 5S)- 5-chloro-5-cyclopentyl-2-pentanol

Nomenclature-Cyclic Alcohols Drop the –e ending of the cycloalkane and add –ol The hydroxyl group is given position “1” trans- 3-ethyl cyclohexanol