Chem 334 - Fall
1999Organic Chemistry I
Dr. Carl C. Wamser
Chem 334 - Fall
1999
know the terminology:
alcohol, hydroxy, thiol, sulfhydryl
hydrogen bonding
dipole-dipole interactions
know the nomenclature rules for alcohols, diols, thiols
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, solubility, and other interactions between molecules
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 that SN2 or E2 mechanisms are favored when there is an unstable carbocation and minimal steric handrance for direct substitution
classify alcohols as 1°, 2°, 3°
write IUPAC names for alcohols, polyols, thiols
write common names for alcohols and thiols
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 with HX, PBr3, or SOCl2
dehydration to alkenes
write mechanisms for substitution and elimination reactions of alcohols
predict relative reactivities of different alcohols
use an appropriate reaction or sequence of reactions to create a target molecule