Chemistry 331 - Fall 1996

Chapter 8 - Alcohols & Ethers

New Skills

Knowledge - Level 1

know the terminology:

alcohol, ether, phenol, quinone, hydroxy, alkoxy, epoxide
thiol, sulfide, disulfide
hydrogen bonding

know the nomenclature rules for alcohols and diols

know the relative acidities of alcohols (pKa ~ 15-18), phenols (pKa ~ 10)

Concepts - Level 2

recognize that hydrogen bonding has a distinctive effect on boiling points and other interactions between molecules

understand the interrelationships between the various oxygen functional groups as different oxidation-reduction states

recognize that alcohols undergo substitution and elimination reactions from their protonated states, so that water is the effective leaving group

recognize that alcohols can act as acids or bases, analogous to water reactions

recognize that ethers are mainly unreactive, with the exceptions being substitution reactions in strong acids (HBr, HI) and epoxides, which easily undergo additions of nucleophiles

recognize the oxidation-reduction reactions often used in biological systems:

quinones / hydroquinones
thiols / disulfides

Applications - Level 3

classify alcohols as 1°, 2°, 3°

write IUPAC names for alcohols, ethers

write common names for phenols, ethers

write acid-base reactions of alcohols and phenols

predict preferred directions of acid-base reactions, knowing pKa values

write various reactions that can be used to prepare alcohols

hydration of alkenes
reduction of carbonyl and carboxyl compounds

write various reactions of alcohols

oxidation to carboxylic acids (1°) or ketones (2°)
oxidation to aldehydes (1° alcohols + PCC)
conversion to alkyl halides

use the Williamson ether synthesis to prepare ethers

use aromatic substitution reactions to make phenols and derivatives

Analytical Skills - Level 4 & higher

write mechanisms for substitution and elimination reactions of alcohols or ethers

write an SN2 mechanism and predict products from nucleophilic addition to epoxides

write synthetic sequences that lead to a target compound