Chem 334 - Fall 1999
Organic Chemistry I

Dr. Carl C. Wamser

Chapter 9 Skills

Knowledge - Level 1

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)

Concepts - Level 2

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

Applications - Level 3

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

Analytical Skills - Level 4

write mechanisms for substitution and elimination reactions of alcohols

predict relative reactivities of different alcohols

Synthetic Skills - Level 5

use an appropriate reaction or sequence of reactions to create a target molecule