CARBOXYLLIC ACIDS

Lab exp3
Abstract

The aim of the experiment is the identification of 4 samples carboxylic acids, their function
group and to learn the chemistry of carboxylic acid. The experimental procedures are as follows:
The first test is the acidty test, carboxylic acid react with Na2CO3 and gives effervescence due
To the evolution of CO2, positive result for acidty. The second test is esterification, where
Acid react with alchol with conc H2SO4 which produces a distinctive odor. FeCl3 test where it
Gives violet color for salicylic acid and rest of the samples gives buff. Bromine water is a test
done on cinnamic acid which gives orange discharge color and phtaline test is done on phtalic
acid and salicylic scid which gives a pink color and flurocesin test on phtalic acind gives a green
color.
Table of Contents
Abstract ......................................................................................................................................................... 1
Introduction .................................................................................................................................................. 3
Experimental Results .................................................................................................................................... 5
Discussion...................................................................................................................................................... 9
References .................................................................................................................................................. 12
Introduction

Acidity of carboxylic acids

Carboxylic acid are acidic due to the hydrogen in its function group (–COOH group).
They are determined by adding Na2CO3 or NaHCO3. When adding sodium bicarbonate
To carboxylic acid it gives an effervescence effect and produces CO2 which shows a positive
result of acidity.

Compassion of acidity for carboxylic acids and phenols(Table 1)

Carboxylic pKa Phenols pKa
acid
Benzoic acid 4.20 Phenol 10

Salicylic acid 2.97 1-Naphthol 9.34

Cinnamic 4.44 Catechol 9.15

acid

(Clark, 2012)
Table 1 shows that carboxylic acids are very acidic compared to phenols
Difference between carboxylic acid & phenols

Resonance structure of Carboxylate ion Resonance structure of phenoxide ion

(Fig1.1) (Fig 1.2)

In Fig (1.1), carboxylate ion is more stabilized by resonance. Even though phenoxide ion is
Stabilized, but its stability is less compared to carboxylate ion. This is due to carboxylate ion
Which has 2 resonance structure, which are equally favored compared to the resonance structure
of pheoxide ion. Carboxylic acid is more acidic than phenol because of the negative charge in
the carboxylate anion is more spread out compared to the phenoxide ion. Carboxylate ion
has two electronegative O-atoms while phenoxide ion has only one. In (fig1.1) carboxylate
ion, its electronegative charge is present on the O-atoms while in (fig 1.2) the negative charge
is present on electropositive carbon atom which leads to less stability of phenoxide ion compared
to carboxylate ion. (Reusch, 2013)
Experimental Results

Carboxylic acids
Unknown 1
Physical Characteristics:

Appearance: white crystals

Color : white

Chemical reactions

Test Observation Result

Acidity test Effervescence Postive result for

acidty. It is an acid

FeCl3 Test Violet color The unknow is a

salicylic acid

Phthalein test pink color The unknown is

salicylic acid

Bromine test No change No reaction occurred

Esterification Test (MeOH) Distinctive odor The unknown is

salicylic acid
Wintergreen odor

Unkown is salicylic acid write the structure

 Carboxylic acids
Unknown 2
Physical Characteristics:

Appearance: crystalline solid

Color : colorless

Chemical reactions

Test Observation Result

Acidity test Effervescence Postive result for

acidty. It is an acid

FeCl3 Test Buff ppt Aromatic carboxylic

acid

Phthalein test No change No reaction occurred

Bromine test No change No reaction occurred

Esterification Test (MeOH) Distinctive odor The unknown is

benzoic acid
sweet odor

Unkown is benzoic acid write the structure

 Carboxylic acids
Unknown 3
Physical Characteristics:

Appearance: crystals

Color : white

Chemical reactions

Test Observation Result

Acidity test Effervescence Postive result for

acidty. It is an acid

FeCl3 Test Buff ppt Aromatic carboxylic

acid

Phthalein test Pink color The unknown is phtalic

acid

Azo dye No change No reaction occurred

Bromine test No change No reaction occurred

Esterification Test (MeOH) Distinctive odor The unknown is

Faint odor phtalic acid

Flurocesin test Green fluroscene The unknown is

phtalic acid

Unkown is phtalic acid write the structure

 Carboxylic acids
Unknown 4
Physical Characteristics:

Appearance: crystals

Color : white

Chemical reactions

Test Observation Result

Acidity test Effervescence Postive result for

acidty. It is an acid

FeCl3 Test Buff ppt Aromatic carboxylic

acid

Phthalein test No change No reaction occured

Bromine test Orange color discharge The unknow is

cinnamic acid

Esterification Test (MeOH) Distinctive odor The unknown is

Fruity odor cinnamic acid

Unkown is cinnamic acid write the structure

Discussion

Unknown 1 (salicylic acid)

The first test is the acidty test which determines the unknown is a carboyxllic acid by the
production of effervescence due to CO2

+ CO2 + H2O

The second test is the FeCl3 which gives violet color for salicylic acid and buff for the rest of the
unknowns. It is used for determining the aromatic acids.

The third test is the phtaline test where it reacts with salicylic acid to produce a red color

The last test is the esterification test which alcohol is added to an acid , producing a distinctive odor

Unknown 2 (benzoic acid)

The first test is the acidty test which determines the unknown is a carboyxllic acid by the
production of effervescence due to CO2
The second test is the FeCl3 which gives violet color for salicylic acid and buff for the rest of the
unknowns for benzoic acid it gives a buff ppt. It is used for determining the aromatic acids.

The last test is the esterification test which alcohol is added to an acid , producing a distinctive odor

Unknown 3 (phtalic acid)

The first test is the acidty test which determines the unknown is a carboyxllic acid by the
production of effervescence due to CO2

The second test is the FeCl3 which gives violet color for salicylic acid and buff for the rest of the
unknowns. It is used for determining the aromatic acids.

The third test is the phtaline test where phenol and H2SO4 to produce phenolphthalein and gives a pink

Color.
Flurocesin test gives is phtalic acid reacting with resorincal + NaOH to give a green fluroscnce color

The last test is the esterification test which alcohol is added to an acid, producing a distinctive odor

Unknown 4 (cinnamic acid)

The first test is the acidty test which determines the unknown is a carboyxllic acid by the
production of effervescence due to CO2

The second test is the FeCl3 which gives violet color for salicylic acid and buff for the rest of the
unknowns. It is used for determining the aromatic acids.

The bromine water test is special reaction for cinnamic acid where it discharge the orange color

The last test is the esterification test which alcohol is added to an acid, producing a distinctive odor
References
Clark, J. (2012). chemwiki. Retrieved from chemwiki:
http://chemwiki.ucdavis.edu/Core/Organic_Chemistry/Alcohols/Properties_of_Alcohols/Backgr
ound

Reusch, W. (2013, 5 5). chemistry.msu.edu. Retrieved from Michigan state university:

https://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/crbacid1.htm