Phenols

Renz S. Bareo, 2Rommel L. Santos, 3John Dahrell J. Vilela

1
Department of Physical Sciences, College of Science, Polytechnic University of the Philippines, Sta.
Mesa, Manila, Philippines
1

Date Performed: December 15, 2014

Date Submitted: January 12, 2015
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Abstract
In this experiment, several tests were conducted to identify and distinguish phenols through its distinct
reactions. These tests were used to determine physical and chemical properties of given test samples that would able
to distinguish each type from the other. The test samples used are phenol, 1-naphthol, catechol, albumin and
salicylic acid. The tests conducted are: ferric chloride test which gives purple color of solution as indication of the
presence of phenols, while formation of white precipitate for bromine water test, and red coloration of solution for
Millons reagent test. Moreover, samples were also tested for its solubility in alkali which would identify formation
of soluble phenolates from phenols.
__________________________________________________________________________

Keywords: phenolates,phenols, ferric chloride test, Millons Test, bromine water test, solubility
Introduction
Phenols are compounds that have hydroxyl group directly attached to a benzene ring. Thus, these
types of compounds are commonly called phenol, a specific name for hydroxybenzene which is the
general name for the family of compounds derived from hydroxybenzene. Phenols have distinctive odor
and usually colorless crystalline compound which however become colored due to oxidation. And due to
the presence hydroxyl groups in phenols, these compounds are like alcohols that are able to form strong
intermolecular hydrogen bonds and therefore have higher boiling points than hydrocarbons of the same
molecular weight. But although phenols are structurally similar to alcohols, phenols are much stronger
acids than alcohols and thus easily soluble in alkali. There are also some phenols where the hydroxyl
group is attached to polycyclic benzenoid ring which are basically similar with phenols but are called
naphthols and phenanthrols (Fryhle and Solomons, 2011).

Phenols are considered to be one of the most essential organic compounds in the field of
pharmaceutical chemistry due to its role in synthesis of drugs like aspirin and as part of many biological
compounds with helpful antioxidant properties like those of vitamins E and C and the carotenoids which
have polyphenols. For instance when synthesizing acetylsalicylic acid or commonly known as aspirin,
salicylic acid, a phenol, is reacted with an excess acetic anhydride in the presence of acid catalyst. And
one of the most important steps in this industrial synthesis is the purity test for aspirin that is confirmed
by a qualitative analysis for determining the presence of salicylic acid, a phenol, as an impurity in the
product. The most commonly used method for detection such type of phenol is the ferric chloride or iron
(III) chloride test. Iron (III) chloride reacts with phenols to produce purple to violet color of solution.

Along with this method are still lots of simple test used to detect or identify phenols. Some of these are
the litmus test, bromine water test, Millons test, Libermann reaction and pthalein test. Thus, these tests
are really considered to be significant in the field of production industry. In such a way that these methods
do not just help them identifying the reagents or materials needed for product but also enables them to
ensure the quality of their commercial products.

Objectives
This experiment aims to determine the physical and chemical properties of phenolic compounds,
specifically the solubility of phenols with alkali compounds such as sodium hydroxide, and through the
reactions of test samples: 1% phenol, 1% catechol and 1% - naphthol, conc. phenol, 1% salicylic acid
and 5% albumin under Ferric Chloride Test, Bromine water Test and Millons Test. And to be able to
distinguish each type of phenol from the rest through their reactions involved in the various tests.
Methodology
I. Solubility in Alkali
To test for solubility of phenols in alkali, 3-mL of 5% NaOH was prepared in a test tube.
Then 1% phenol is added to it drop wise. Afterwards, shake and observe the test sample.
II. Reaction with Ferric Chloride ( FeCl3 )
In separate test tubes, 1-mL of each test sample, specifically 1% phenol, 1% catechol, and
1% -naphthol were prepared. This is followed afterwards by addition of 1 drop of 1%
FeCl3 to each test tube. The color changes were observed and noted.
III. Bromine Water Test
To conduct the bromine water test, test samples of 1-mL volume were prepared in
separate test tubes. Afterwards, brominated water was added to each test sample drop by
drop until formation of precipitate was observed.
IV. Millons Test
In separate test tubes, 1-mL each of 1% phenol and 5% albumin were prepared. Then
into the two separate test tubes, 6 drops of Millons reagent was added. Afterwards, the
solution was shaken then boiled in a water bath until a color was produced.

Result and Discussion

I. Solubility in Alkali

In this figure, it shows that 1% phenol when dissolved with 5% sodium

hydroxide formed a colorless solution with no precipitate. This observation
leads to a fact that the phenol is soluble with alkali or strong base sodium
hydroxide.
It is because in this reaction, phenol, a weak acid reacted with sodium
hydroxide which is a strong base to form sodium phenoxide and water. This
reaction just implies that phenols react with the strong bases to form phenoxide
ions, considering that the phenol is not highly hindered. Moreover, a part of this
exception is the reaction of electron-withdrawing-free phenols with weak bases
like sodium bicarbonate. This exception makes phenols different among the
Figure 1: 1%
Phenol dissolved
in 5% NaOH

other acids.

II. Reaction with Ferric Chloride ( FeCl3 )

Table 1: Summary of Results for Ferric Chloride Test

Test Sample
1% Phenol
1% Catechol
1% 1-Naphthol

Figure 2: Test Samples : 1% Phenol (left), 1%

Catechol (middle), 1% Naphthol (right)

Color of Solution
after 1% FeCl3
addition
Purple to intense violet
Yellow to orange
Orange

Remarks
Positive
Negative
Negative

The figure shows that the test samples: phenol,

catechol and naphthol when reacted with 1% FeCl3

forms violet, yellow, and orange-colored solutions, respectively. These color changes observed with the
test sample are summarized in the table with its remarks.
When the 1% phenol reacted with 1% FeCl3 the solution turned out to be a purple to intense
violet-colored solution. The purple to violet color of solution indicates the presence of phenol in the
solution upon complex-ion formation of ferric phenoxide which absorbs visible light to give an excited
state over both iron atom and conjugated organic system. While catechol and naphthol produced

yellowish orange and orange solution, respectively. This observation indicates that the two phenols are
hindered phenols which may not always react with ferric chloride test.
III. Bromine Water Test
This figure shows when reacted with the bromine water, the
concentrated phenol formed a turbid solution with white precipitates. While
on the other hand, the salicylic acid formed only a clear solution with no
precipitate observed.
The significance of this observation is the formation of 2,4,6tribromophenol which is the white precipitate formed in the solution of
concentrated phenol reacted with bromine water. The white precipitate
indicates that the bromine in excess in the brominated water reacts with the
phenol in ortho-para direction of electrophilic aromatic substitution with
respect to the hydroxyl group, a strong electron donating group and ring
Figure 3: Conc. Phenol (right)
and Salicylic Acid (left) with
Bromine water

activator forming 2,4,6-tribromophenol.

IV. Millons Test

This figure shows that upon addition of Millons reagent, the test samples
1% phenol and 5% albumin formed solutions of red with black precipitate and
colorless with yellow precipitate, respectively.
The red coloration of the 1% phenol with millons reagent indicated the
formation of p-nitrosophenol and a distinct compound which is red in acidic
solution. Moreover, it is found out that p-nitrosophenol in the solution reacts with
the mercurous nitrate in the solution forming red, brown or black precipitates
(Gibbs, 1927).

Conclusion

Figure 4: Millon's Test Samples;

1% phenol(left) and 5%
Albumin (right)

Given the observation and results of all the tests conducted to identify phenols, this experiment
concludes that phenols can be distinguished from alcohols due to its stronger acidity and reaction with
alkali which forms aqueous sodium phenoxide. And also from other compounds through various tests like
ferric chloride test which detects the presence of phenol in a sample solution by turning its color into

purple to intense violet upon formation of ferric phenoxide ion. However, its also noted that highly
hindered phenols may not react with iron (III) chloride thus may not change into purple color. While for
Millons test, a red coloration with the solution of phenol sample upon reaction with Millons reagent
indicates a positive result. But for bromine water test formation of white precipitate or 2,4,6tribromophenol indicates the presence of unhindered phenol or monhydroxy phenol in the sample.

References
1. Lontoc, B.Laboratory Manual in Basic Organic Chemistry. Department of Physical Sciences:
Centro Escolar University, 2004.
2. Gibbs, H.D. Phenol Tests: II. Nitrous Acid Tests. The Millon And Similar
Tests.Spectrophotometric Investigations. J. Biol. Chem. [Online] 1927, 71, 445-459.
http://www.jbc.org/content/71/2/445.full.pdf (accessed Dec 23, 2014).
3. Fryhle, Craig B.; Solomons, Graham T.W.: Organic Chemistry, 10th ed.; John Wiley & Sons,
Inc.: United States of America, 2011.
4. Sethi, Arun. Systematic Lab Experiments in Organic Chemistry. New Age International (P)
Ltd., Publishers: Lucknow, India, 2003.