Alcohols I is the first of a two part study of compounds containing the OH
functional group. It includes structure and naming of alcohols,
common alcohols and their usage, physical properties and preparations
of alcohols. A section addressing thiols is included. A separate
unit on reactions and analysis of alcohols is addressed in
The structure surrounding the functional group of alcohols is compared
to that of water so students may better understand the role alcohols
will play in formation of hydrogen bonding. The boiling points of
alcohols are compared to boiling points of alkanes of similar molecular
weight to again reinforce the impact of hydrogen bonding on molecular
Nomenclature of alcohols is addressed from both the systematic (predominately
IUPAC) and common approach. A section using the old carbinol method
of alcohol nomenclature is also included.
Some common alcohols, their properties, and uses within the world
of the layman are introduced: methyl alcohol, ethyl alcohol, isopropyl
alcohol, ethylene glycol, and glycerol. The terms used by the layman
such as wood alcohol, grain alcohol, and the like are explained.
Hazards of these five alcohols which find significant common application
are discussed and described.
Preparations of alcohols treated in this unit include hydrolysis
of alkenes, oxymercuration/demercuration, hydroboration/oxidation,
hydroxylation, hydrolysis of alkyl halides, reduction of carbonyls,
and the Grignard. The student is reminded that preparations of one
functional group are often reactions of another functional group
so that the orderliness of organic chemistry is stressed. This becomes
particularly apparent in this unit on Alcohols I.
Hydroxylation using permanganate followed by sodium hydrogen sulfate
is used to prepare a diol from an olefin, but the fact that the
reaction also works well using oxmium tetroxide is noted. In both
cases, the syn, rather than the anti addition is shown to occur.
Prior to discussing reduction of carbonyls as a method of preparing
alcohols, the order of oxidation and reduction for organic compounds
is developed. The idea is that organic students presented with the
logical progression of oxidation and reduction will find the numerous
oxidation and reduction reactions they study much easier to grasp.
The problems of which oxidizing agent and which reducing agent to
use are also addressed, with particular emphasis placed on the three
classic reducing agents: sodium borohydride, lithium aluminum hydride,
and hydrogen with a catalyst.
The structure, physical properties, and nomenclature of thiols are
introduced in a section at the end of this unit. Both systematic
and common names are discussed as is oxidation and reduction regarding