Table1.

Nucleophilic acyl Substitution (NAS): Esterification

Carboxylic Acid
(structure)
Salicylic Acid

Nucleophile
(-OH compound)
Methanol

Description of product
Clear solution with minty smell

Chem
rxn
1

Chemical Equation:
1

C7H6O3 + CH3OH C8H8O3 + H2O

Table2.1 Acidity of Carboxylic Acid (Salt formation)

Carboxylic Acid
Acetic Acid
Benzoic Acid

Description of acid with

Orange solution
Clear solution with orange ppt

Base
NaOH

Rxn
2a

NH4OH

2b

Chemical Equation:
2a

NaOH + CH3COOH CH3COONa + H2O

FeCl3 + CH3COONa Fe(CH3COO)3 + NaCl

2b

C6H5COOH + NH4OH C6H5COONH4 + H2O

Table2.2 Ferric Chloride Test for Carboxylate Group

Carboxylate Salt
Sodium Acetate
Ammonium Benzoate

Description with salt

Rxn

Chemical Equation:
2c

2d

Table3. Nucleophilic Acyl Substitution (NAS): Hydrolysis of Acid Derivatives

Acid Derivatives
Acyl Chloride
(R-COCl)
Acetyl Chloride
Acid Anhydride
(R-COOOC-R)
Acetic anhydride

Odor/Relative Temp
Smelled like vinegar ,
sour smell
Solution having an oily
substance then turned to
light pitch color then a
few min sol. turned to
clear

Relative Rate of NAS

rxn
Faster

Rxn

3a
Slow
3b

Chemical Equation:
Acid Derivative
Acid Amide (1o)
R-C=O
NH2 Acetamide

Litmus test of vapor

red litmus paper to blue (vapor)

Chemical Equation:
3a

CH3COCl + H2O CH3COOH + HCl

3b

(CH3CO)2 + H2O 2CH3COOH

3c

CH3CONH2 + NaOH CH3CO2Na + NH3

Rxn
3c

Table4. Decarboxylation of Dicarboxylic Acids

Dicarboxylic
Acid
Oxalic acid
Succinic acid

Description on
heating
Turns to liquid then
gas
Turns to liquid then
gas

Chem
rxn
4a

Description of gas plus lime

water
Produced white precipitate

Chem
rxn
4b

4c

Did not produced

precipatate

4d

Chemical Equation:
4a

H2C2O4 HCOOH + CO2

4b

CO2 + Ca(OH)2 CaCO3 + H2O

4c

4d

Discussion
In esterification, salicylic acid was mixed together with 5 drops of methanol
and concentrated H2SO4. The solution was then heated. It has a minty odor.
Esterification took place when methanol was added. The assault of the nucleophilic
species, for this situation, CH 3OH, would prompt separation of carbon-oxygen bond,
which is generally known as acyl-oxygen kind of separation, showed by the onset of
pleasant smell. Esters are created when carboxylic acids are warmed with alcohols
in the presence of an acid catalyst. The catalyst is the sulphuric acid. The
esterification reaction is both slow and reversible. The name of this ester is methyl
salicylate or vanillin.
The ferric chloride test is used to determine the presence or absence of
phenols in a given sample. Enols give positive results as well. The bromine test is

useful to confirm the result. Phenols form a complex with Fe(III), which is intensely
colored. This is the basis for the test.The sample is dissolved in water, or a mixture
of water and ethanol, and a few drops of dilute ferric chloride solution is added. The
formation of a red, blue, green, or purple coloration indicates the presence of
phenols. Where the sample is insoluble in water, it may be dissolved in
dichloromethane with a small amount of pyridine.
In reaction of acid derivatives, there were three solutions used. Five drops of
water was added to two drops of acetyl chloride. It has a sour smell and reacted
faster than acetic anhydride. It responded that way in light of the fact that the C-O
bond is extremely strong, much stronger than the C-Cl bond. The change in
reactivity is dramatic. In homogeneous solvent systems, response of acyl chlorides
with water happens quickly, and does not oblige warming or catalysts. Amides, then
again, respond with water just in the presence of strong acid or base catalysts and
outer warming. Five drops of water was also added to acetic anhydride. It has
slower reaction that the acetyl chloride. With an acid anhydride, the reaction is
slower, but the only essential difference is that instead of hydrogen chloride being
produced as the other product. The responses (of both acyl chlorides and acid
anhydrides) include things like water, alcohols and phenols, or ammonia and
amines. These specific cases contain an extremely electronegative component with
a dynamic lone pair of electrons - either oxygen or nitrogen. Last procedure in
reaction of acid derivatives, dilute NaOH solution was added to one small crystal of
acetamide. The gas evolved is NH3. This hydrolysis is difficult because the C-N bond
is very strong, and its stabilized by resonance. Its catalyzed by OH-.
Reactivity: acyl halides > anhydrides >> esters acids >> amides
In reactions of dicarboxylic acids, 0.1 g of oxalic acid was heated with a
delivery tube connected to the lime water was heated. The limewater test is the
classic test for CO2. When CO2 gas is bubbled into limewater, a saturated solution
of calcium hydroxide, the solution becomes cloudy. The cloudiness is due to the
formation of insoluble calcium carbonate. Dicarboxylic acids such as oxalic acid
experience warm decarboxylation as well as forms various metallic salts which has
remarkable properties. For this situation, oxalic acid in its salt structure can remove
rust. Oxalic acids can break up rust like stain rust in a material, contingent on the
solvency of heavy metal oxalates in arrangements of soluble base oxalates.
Conclusion
In conclusion, the structure of the compounds plays an important role in its
solubility. Carboxylic acids undergo reactions to produce derivatives of the acid.
Electronegativity plays a big role on the carboxylic acids acidity. Carboxylic acids
are usually resistant to oxidization but there are some cases that they can be
oxidized.

Esterification took place when methanol was added. Acid anhydride

formation, this group forms by reacting the salt of a carboxylic acid with an acyl
halide. Decarboxylation is the loss of the acid functional group as carbon dioxide
from a carboxylic acid. The reaction product is usually a halocompound or an
aliphatic or aromatic hydrocarbon . In reactions of dicarboxylic acids, gas formed
when CO2 gas is bubbled into limewater.