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ABSTRACT
Carboxylic acids and their derivatives are organic compounds that bears an acyl group
that may be attached to an electronegative atom such as oxygen, nitrogen or sulfur, or a
substituent (-Y) that can act as the leaving group in nucleophilic acyl substituion (S N Acyl). In SN
Acyl, carboxylic acids and their acid derivatives would act as an electrophile and would be
attacked by a nucleophile. All carboxylic acid derivatives if subjected to hydrolysis would
produce their corresponding parent carboxylic acid. Among all the acid derivatives acyl halides
are the most reactive and amides are the least. The objective of this experiment is to distinguish
the different carboxylic acids and their derivatives and to classify them according to their
reactivities. Classification tests such as hydrolysis, alcoholysis, aminolysis and hydroxamic acid
test was performed on acetyl chloride, acetic anhydride, ethyl acetate, acetamide and
benzamide. The results has shown that positive results such as the odor, precipitate formed and
evolution of a gas in hydrolysis would determine the presence of their carboxylic acids. This is
true for acetyl chloride, acetic anhydride, ethyl acetate and benzamide. While the odor of the
resulting mixture in alcoholysis proves the presence of the ester that was formed upon addition
of ethanol to acetic acid, acetyl chloride and acetic anhydride. Formation of a white precipitate in
aminolysis of acetyl chloride and acetic anhydride is a positive result of the presence of an
anilide which is acetanilide. Hydroxamic Acid Test is used to identify the presence of the
functional group of esters and amides. A positive result of red-purple colored solution was seen
in ethyl acetate and acetamide. Overall, determining the reactivities of carboxylic acids and their
derivatives can be obtained by performing different classification tests. This is made possible
due to the difference in their substituents and the reagents used.
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INTRODUCTION
Carboxylic
Acid
derivatives
are
group
in
nucleophilic
acyl
All
acid
derivatives
can
be
converted
severe.
into
many
other
kinds
of
mechanism.
group
to
give
tetrahedral
I.
A. Acyl
RC(O)N(OH)R1 which is
halides
and
Acid
anhydrides
usually
hydroxamic acid.
1 mL of
carboxylic
acids.
Hydroxamic
Acid
Formation
of
precipitate
was
of
saturated
NaHCO3
was
observed.
B. Esters
The sample used for the
the
distinguish
to
differentiate
the
them
reactivities
using
of
different
classification tests.
the
experiment
to
prevent
possible
C. Amides
added
to
each
test
tube.
The
III.
Anhydrides
change
of
color
was
observed.
II.
Alcoholysis : Schotten-Baumann
Reaction
A. Acetic Acid
observed.
IV.
B. Acyl
halides
and
Acid
anhydrides
second
test
tube,
0.5
mL
showed
bubbling
effect
Sample
Warming
effect
Upon
addition
of
2%
AgNO3
Upon
addition
of
saturate
d
NaHCO3
Acetyl
Chloride
Warm
(+)
White
ppt (+)
Bubbling
effect (+)
Acetic
Anhydrid
e
Room
Temp (-)
Turbid
solution
Bubbling
effect (+)
Sample
Observations
Ethyl Acetate
acetyl chloride.
underwent
an
exothermal
would
show
the
formation
of
Sample
Observations
Benzamide
Sample
Odor
Formation of
layers
Acetyl
Chloride
Fruity
None
Acetic
Anhydride
Fruity
None
Sample
Observations
Acetic Acid
Alcoholysis
or
esterification
and
Sample
Appearance
of Precipitate
Upon
additiom
water
Acetyl
Chloride
White ppt
dissolved
Acetic
Anhydride
No ppt
(-)
solution
of
A positive result is exhibited by a
red-purple color solution. According to Table
7, both ethyl acetate and acetamide turned
into a brown turbid solution upon addition of
5%
FeCl3.
The
solution
was
actually
chloride
of
result.
is
due
to
the
formation
CONCLUSION
It can be concluded that several
classification tests can be conducted to
differentiate the reactions of carboxylic acids
and their derivatives. Nucleophilic acyl
Sample
Upon addition of 5%
FeCl3
Ethyl Acetate
Brown
solution
turbid
Acetamide
Brown
turbid
alcoholysis
and
aminolysis
undergoes.
Hydrolysis of acetyl chloride, acetic
anhydride, ethyl acetate and benzamide
showed
positive
results
to
prove
the
http://www.vanderbilt.edu/AnS/Chemistr
y/Rizzo/Chem220b/Ch20.pdf
have
been
due
to
possible
the
experiment
was