1. 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 Substitution to R-X (SN1, SN2) (c) ROH as a nucleophile (ether synthesis - SN2)
Reactions of Epoxides – Stereospecific (SN1 or SN2)

2. 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

3. 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

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