know the terminology:
alcohol, ether, hydroxy, alkoxy, epoxide
thiol, sulfide, disulfide
hydrogen bonding
know the nomenclature rules for alcohols, diols, ethers, thiols, sulfides
know the relative acidities of alcohols (pKa ~ 15-18), thiols (pKa ~ 8-9)
recognize that alcohols can act as acids or bases, analogous to water reactions
recognize that hydrogen bonding has a distinctive effect on boiling points and other interactions between molecules like solubility
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
understand the SN1 and SN2 mechanisms as different ways of accomplishing a substitution reaction
understand the E1 and E2 mechanisms as different ways of accomplishing an elimination reaction
recognize the importance of carbocation stability in determining the favorability of an SN1 or E1 mechanism
recognize that SN2 or E2 mechanisms are favored when there is an unstable carbocation and minimal steric hindrance for direct substitution
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
classify alcohols as 1°, 2°, 3°
write IUPAC names for alcohols, ethers, thiols
write common names for ethers and sulfides
write acid-base reactions of alcohols and thiols
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
dehydration to alkenes
write mechanisms for substitution and elimination reactions of alcohols or ethers
write mechanisms for addition reactions of epoxides, using acid or base
write synthetic sequences that lead to a target compound