is treated as a separate unit by the Chemistry Professor to allow
inclusion at any point in the course. The topics addressed include
nomenclature, physical properties, preparations, reactions, and
In order to prevent confusion for the organic student, it is necessary
to separate the study of phenols from the study of alcohols. Otherwise,
there is a tendency among the novices to think of phenols
as alcohols. Some textbook authors choose to place a study of phenols
with a study of aromatics. Placing phenols in a separate unit permits
their inclusion at whatever point the particular course designer
feels is appropriate.
The nomenclature of phenols addresses those unique names such as
the cresols, catechol and friends, salicylic acid, vanillin, etc.
Accompanying nomenclature is a study of physical properties, particularly
the interesting differences in solubilities, as in the catechol
group. Students see the impact of physical positioning of substituted
rings when faced with the question of why the solubilities of catechol,
resorcinol, and hydroquinone differ so markedly.
Also addressed are the factors that impact the acidity of phenols.
The question of why phenols are so much more acidic than alcohols
is answered by showing the equilibrium components that stabilize
the phenoxide ion. Problems addressing Ka of phenols help develop
an understanding of the limited acidity of these compounds. That
their acidity is sufficient for them to act as a good bactericide
Two preparations are treated for phenols: diazzonium salts and benzenesulfonic
acid. The reasons the first is a good lab preparation and the second
is a good industrial preparation are addressed.
The reactions of phenols addressed include neutralization, halogenation
with chlorine, halogenation with bromine, nitration, sulfonation,
Friedel-Crafts alkylation, oxidation, the Fries rearrangement, the
Kolbe reaction. The ability of the OH group on phenols to act as
a powerful activator changes the conditions required for electrophilic
aromatic substitution. This is particularly noted in the manner
in which halogenation and several other of the reactions proceeds.
The mechanisms for each of the reactions is discussed and explained.
The carbonation via the Kolbe reaction is presented as a method
of producing salicylic acid.
Analysis of phenols involves test tube tests to suggest the presence
of this somewhat acidic group: pH, no effervescence of bicarbonate
solutions, and the formation of a yellow precipitate when phenols
are treated with bromine water. The major absorption bands are suggested
for IR identification, as well as the distinctive features found
in the HNMR and the UV-VIS. In mass spec, the prominent parent peak
which may be the base peak is discussed.
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