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Acid Derivatives introduces five classes of organic compounds: acid
chlorides, amides, acid anhydrides, esters, and nitriles. The structure,
preparation, and reactions of each of these five classes are studied,
as well as chemical and spectroscopic analysis. The unit concludes
with presentation of organic group nomenclature priorities.
The unit begins with the structures of these five classes of compounds
and how these structures are generally written. Students are reminded
throughout the unit that these classes of compounds are strongly
related. The reactions of one well may be seen again as the preparation
for another. This helps the student understand that the mastering
of five classes in one unit is not unreasonable. In each of the
five classes, nomenclature, physical properties, preparations, and
reactions are addressed. The unit concludes with a section on chemical
and spectroscopic analysis of all five classes.
Following a discussion of the nomenclature of acid chlorides, the
most commonly referenced preparation is presented: nucleophilic
acyl substitution using a reagent such as thionyl chloride with
carboxylic acid. The reactions of acid chlorides addressed include
Friedel-Crafts acylation, reaction with organo cadmium, the Rosenmund
reduction, and a series of substitution reactions.
The study of amides also begins with a section on nomenclature.
In the preparations of amides, the nucleophilic acyl substitution
using acid chlorides with ammonia or amines is addressed, as are
those using esters and anhydrides with ammonia. Because amides are
the most stable of the acid derivatives, they are not very reactive,
so only two new reactions are addressed and several old ones are
After a section addressing nomenclature and properties of esters,
the preparations are considered. Most of these preparations are
review, but several additional points are addressed. The preparations
considered are preparation from acid chlorides, the Fischer esterifications,
lactone formation, and the reaction of alcohols with anhydrides.
Mechanisms for many of these are addressed, particularly the two
mechanisms for the Fischer esterification and where beneficial,
these mechanisms are animated. The reactions of esters considered
include hydrolysis in an acid, hydrolysis in a base, trans-esterification,
ammonolysis, reaction with Grignard, and reduction of esters. In
this last one, four methods of reduction are considered with advantages
and disadvantages of each.
of acid derivatives includes test tube analysis where feasible,
such as the ability of acid chlorides to form precipitates with
silver nitrate solutions. Spectroscopic analysis includes characteristic
signals of infrared and NMR for the five classes. The unit concludes
with a section addressing nomenclature priorities.
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