CHM142L Organic Chemistry 2 Laboratory

3nd Quarter SY 2015-2016

Alcohol and Phenols

Tagalog, Christian1, Tolentino, Aika Cecille, I.2, Terrado, Rence3, Valencia, Ifame4

Prof. Oliver, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; 1Christian
Tagalog, CHM143L/A31, School of Chemical Engineering and Chemistry, Chemical Engineering, Mapua Institute of
Technology, 2Aika Tolentino, CHM143L/A31, School of Chemical Engineering and Chemistry, Chemical Engineering, Mapua
Institute of Technology, 3Rence Terrado, CHM143L/A31, School of Chemical Engineering and Chemistry, Chemical
Engineering, Mapua Institute of Technology, 4Ifame Valencia, CHM143L/A31, School of Chemical Engineering and
Chemistry, Chemical Engineering, Mapua Institute of Technology,

ABSTRACT
Alcohols are any organic compound that has the formula R-OH. Phenol is a
special kind of alcohol. It is comprised of a hydroxyl group attached directly to
a phenyl ring. The experiment aimed to examine and differentiate the
properties of alcohols and phenols. Both physical and chemical properties of
alcohols and phenols are observed. The student used two different test to
distinguish whether a compound is an alcohol or phenol. Solubility test is the
first method used wherein the test compounds were dissolved in water. Acidity
test is the second test in which the solutions of ethyl alcohol and phenol from
the solubility test were determined as acidic/basic through their approximate
ph value. Additional test were also made in classification of the alcohol's class
based on their reactivity. To determine whether it is primary, secondary, or
tertiary alcohol, we used acid-base reaction test, reaction with acetyl chloride
test, Lucas Test, its oxidation, iodoform test, bromine water test, and ferric
chloride test. The idea of this lab report was to show that alcohols and phenols
are quite different in terms of their physical and chemical properties. The first
part of this report involves a brief summary of the background ideas about
the basic principles of an alcohol and phenol. The next approach taken
was, analyzing the result data from the methods used to create a new
ideas out of the background ideas which were collected. Experiment
findings show alcohol is miscible while phenol is water-insoluble. Also,
phenols is more acidic than an alcohol due to its resonance. This lab
report provide useful information especially for the student (have an
authorized only) who plans to get some ideas about alcohols and
phenols.

Keywords: Lucas Test, alcohol, phenol, solubility, acidity, iodoform test, primary alcohol

INTRODUCTION water, alcohols can behave either acids or

bases, depending on their chemical
Alcohols are organic compounds that environment:
contain the hydroxyl group (-OH). The
general formula of an alcohol is ROH in
which the R is an aliphatic hydrocarbon
group. Alcohols have some similarities to Like waters, alcohols can be protonated (left) or
water which are important to mention. Like deprotonated (right).

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test, bromine water test, and ferric

Because alcohols contain an -OH group, chloride test);sought to analyze the
they are able to form hydrogen bonds to hydroxyl group, and the functional group
one another. They therefore have high present in alcohols; to classify the alcohols
boiling points. Alcohols can also form as primary, secondary, or tertiary.
hydrogen bonds with water, consequently
the solubility of an alcohol is dependent to
the length of the carbon chain and the MATERIALS AND METHODS
shape of the molecule. Small (short-chain)
A proper attire was strictly followed to
alcohols, are water-soluble. As the
minimize the impact of accidents that
hydrocarbon chain of an alcohol gets
might occur during the experiments.
larger, the alcohol becomes less water
Especially, protective goggles and mask
soluble.
was worn to avoid injury.
Another property of an alcohol is the
The reagents used for this experiment
acidity. Acidity of an alcohol varies with the
were ethyl alcohol, tert-butyl alcohol,
stability of the conjugate base of an
phenol, acetyl chloride, 10% K2Cr2O7, std.
alcohol. Increasing the stability of the
bromine water solution, n-butyl alcohol,
conjugate base of an alcohol, increase the
benzyl alcohol, 10% FeCl 3, lucas reagent,
acidity of the alcohol. Phenols are aromatic
4M NaOH, sec-butyl alcohol, glycerol,
alcohols, in which R is an aromatic ring.
sodium metal, dilute H2SO4 and iodine in
Phenol is somewhat soluble in water. It
potassium iodide solution. As for
acts as a weak acid in water. Though
apparatus, droppers, pH paper,
comparing phenol's acidity to others
thermometer, test tube rack, hot plate,
alcohols, phenol is more acidic among the
litmus paper, micro test tubes with cork
alcohols due to its resonance. The acidity
stopper, water bath and lighted splinter
of phenols is one of the reasons that
were used. These apparatus were cleaned
phenols are a special category of alcohols.
before performing the experiment to avoid
possible source of error in the process.
Alcohols can be classified as primary,
secondary, or tertiary. This classification is
For the first part of the experiment, testing
based on whether the alcohol carbon is
for the solubility of alcohols, a 20 drops of
attached to one, two, or three alkyl groups.
the ethyl alcohol, n-butyl alcohol, sec-butyl
Each classes of alcohols react differently in
alcohol, tert-butyl alcohol, benzyl alcohol
every reaction.
glycerol and phenol were transfer in
separated test tubes. Then, a 40 drops of
water were added to each test tubes. An
additional 80 drops of water were added in
the test tubes if cloudiness appeared in
the solution.

This experiment aimed to examine and For the second part of the experiment, it is
differentiate the properties of alcohols and further broken down to eight parts. This
phenols. More specifically, this study will part is to test whether a compound is an
cover 9 chemical tests (solubility, acidity, alcohol or phenol. For the first part of this
acid-base reaction, reaction with acetyl part two of experiment, the acidity and
chloride, Lucas Test, oxidation, Iodoform basicity of compound are tested. The test

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tubes of ethyl alcohol and phenol from part For part g, phenol and benzyl alcohol was
one of the experiment were used as a test placed in separated 40 drops of water in
compounds. Blue litmus paper and pH the test tubes. Saturated bromine water
paper were used to test for acidity or was added drop by drop until a change is
basicity of each solution. observed.

For part b of the part two of the For part h, the last part of the second part
experiment, a small pellet of sodium were of experiment, 5 drops of 10% FeCl3
added to 80 drops of n-butyl alcohol, sec- solution was placed in 2 micro test tubes,
butyl alcohol, tert-butyl alcohol and then a three drops of phenol to one test
phenol. There rate of gas evolution was tube and 1 crystal of benzyl alcohol to the
compared and the gas was tested with a other were added.
lighted splinter.

For part c, five drops of ethyl alcohol and RESULTS and DISCUSSIONS
phenol was placed separated in a micro
test tube. Then, a drop wise of about three I. Solubility
to four drops of acetyl chloride was added
to each test tubes. The mixture was Table 1.1 (Solubility of the compound)
allowed to stand for two minutes then 40
COMPOUN SOLUBLE INSOLUBL
drops of distilled water was added to each
D E
test tubes.
Ethyl alcohol ⁄
For part d, 80 drops of lucas reagent was
placed in three micro test tubes, Three to n-butyl ⁄
four drops of n-butyl alcohol, sec-butyl alcohol
alcohol and tert-butyl alcohol was added in Sec-butyl ⁄
each of the test tubes at the same time. It alcohol
was shaken vigorously. The mixture was
allowed to stand for 15 minutes with Tert-butyl ⁄
periodic shaking. alcohol

For part e, 10 drops of dilute sulfuric acid Benzyl ⁄

alcohol
and two drops of 10% K2Cr2O7 solution was
added to 5 drops of ethyl alcohol, isopropyl Glycerol ⁄
alcohol and tert-butyl alcohol. It was
warmed gently. Phenol ⁄

For part f, 5 drops of ethyl alcohol and

Based on Table 1.1, among the seven
isopropyl alcohol was placed in separated alcohols, only Benzyl alcohol and Phenol
40 drops of water. 5 drops of 4M NaOH was
are insoluble in water. Solubility of an
added in each of the solution. A solution of alcohol varies with hydrocarbon chain.
iodine in potassium iodide was added drop
Ethyl alcohol, n-butyl alcohol, Sec-butyl
wise while shaking until pale yellow color alcohol, Tert-butyl alcohol, and Glycerol are
persisted. The mixture was warmed in a
4-carbon structure alcohols. These five are
water bath at 60°C. It was set aside for 5- classified as small alcohols since they
15 minutes before observation.
contain less than 6 carbons. In contrast

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benzyl alcohol and glycerol are both Table 2.2A (Reaction of the compound to
classified as large alcohols because they sodium)
contain more than 6 carbon atoms. . As
the number of carbon increases, solubility COMPOUND OBSERVATION
in water decreases due to the carbon chain n-butyl alcohol It is colorless when
that repels the water. The reason for this is reacted with the
the old "like dissolves like" rule. In short, sodium.
solvents tend to be best at dissolving Heat evolved.
compunds with similar polarities, and short The sodium is
hydrocarbon chain alcohols tend to be far completely
more polar (like water) than long dissolved.
hydrocarbon chain alcohols.
Sec-butyl alcohol It is white in color
II. Test for Alcohol and Phenol when reacted with
sodium.
a. Acidity/Basicity Heat evolved.
Table 2.1. (Acidity or Basicity of the The sodium is not
compound) dissolved
completely.
Compou Rxn Rxn Literatu
nd with with pH re Value Tert-butyl alcohol It is in light yellow
litmus paper color after the
paper reaction.
Heat evolved.
Ethyl Blue 5 7.33
The sodium is not
Alcohol
dissolved
Phenol Red 4 5-6 completely.

Comparing the acidity of the phenols and phenol It is peach in color

ethyl alcohols, as shown in Table 2.1, after the reaction
phenols tends to be more acidic than with sodium.
ethyl alcohol. According to literature Heat evolved.
value, ethyl alcohol has 7.33 scale while The sodium is
phenols has 5-6. There are three factors completely
affecting the acidity of alcohols. It might dissolved.
be due to resonance, induction effect, or
Base on Table 2.2A, n-butyl alcohol and phenol
solvation effects. Acidity of an alcohol
dissolved completely in sodium unlike sec-butyl
varies with the stability of the conjugate
alcohol and tert-butyl alcohol. The rate of reaction of
base of an alcohol. Increasing the stability
of the conjugate base of an alcohol, an acid-base reaction depends on the structure of
increase the acidity of an alcohol. The the alcohol. Phenol and n-butyl alcohol is classified as
conjugate base of phenol (phenolate) is primary alcohol, sec-butyl alcohol as secondary
more stable than the conjugate base of alcohol, and tert-butyl as tertiary alcohol. In this acid-
ethyl alcohol (alkoxide) due to resonance base reaction, primary alcohol is more favored,
therefore phenol will be more acidic. followed by secondary alcohol and tertiary alcohol
that's the reason why n-butyl and phenol react
completely.
b. Reaction with Sodium

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Table 2.2B (Reaction involved)

REACTIONS INVOLVED
n-butyl alcohol and sodium Phenol and Acetyl chloride

sec-butyl alcohol and sodium

According to the observations (Table2.3A),

only phenol formed a top layer while ethyl
alcohol was totally dissolve and has no top
tert-butyl alcohol and sodium layer formation. An ester is indicated by
the formation of a top layer. Thus, only
phenols formed an ester. But based on
Table 2.3B, both ethyl alcohol and phenol
have formed ester. Esters are formed when
Phenol and sodium acetyl chloride reacts with a primary or
secondary alcohol . An alkyl halide are
formed when a tertiary alcohol reacts to
acetyl chloride. In the case of phenol and
ethyl alcohol, both of them are primary
alcohols. Therefore, they are both
expected to form an ester which is
In table 2.2B, the formations of alkoxides indicated by the formation of a top layer
and hyrdrogen gas were shown when 1 when reacted to acetyl chloride.
group metal sodium added to each given
alcohol. In this acid-base reaction, the d. Lucas Test
sodium reacts to the hydrogen of the Table 2.4A (Reaction of the compound to
hydroxyl group to liberate hydrogen gas lucas reagent)
and alkoxide.
COMPOUND OBSERVATION
c. Reaction to Acetyl Chloride
n-butyl alcohol No reaction
Table 2.3A (Reaction of the compound to
acetyl chloride) Sec-butyl alcohol No reaction
COMPOUND OBSERVATION Tert-butyl alcohol No reaction
Ethyl alcohol Soluble
Table 2.4B (Reaction involved)
Phenol Layer was formed. It
is not soluble REACTIONS INVOLVED
n-butyl alcohol and lucas reagent

Table 2.3B (Reaction involved)

REACTIONS INVOLVED sec-butyl alcohol and lucas reagent

Ethyl alcohol and Acetyl chloride

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(darkish) alcohol
Isopropyl Blue (with Rubbing
alcohol green alcohol
tert-butyl alcohol and lucas reagent shade)
Tert-butyl Orange undefined
alcohol

Table 2.5B (Reaction involved)

Based from the table 2.4A, there was no REACTIONS INVOLVED
reaction observed for all the test
compounds. The only correct data Ethyl alcohol
obtained was n-butyl alcohol. It was an
error that there was no reaction observed
to the sec-butyl alcohol and tertiary
alcohol because these secondary and
tertiary alcohol would automatically
Isopropyl alcohol
reacted with the lucas reagent because of
the stability of their carbocation. Tert-butyl
alcohol undergo the most stable reaction
while the n-butyl alcohol undergo the least
stable reaction.

The Lucas test is a test that categorize the Tert-butyl alcohol

different types of alcohols based on the
time taken to form a turbid solution or
precipitate using the lucas reagent. There
is no visible reaction in primary alcohol
when undergo the lucas test while in the
secondary alcohol, the solution will turn
cloudy after 5-20 minutes. Then, for the Based from table 2.5A, the ethyl alcohol
teriary alcohol, the solution will turn cloudy and isopropyl alcohol are oxidized to
and two layers will be formed. carboxylic acid and ketone respectively
while in the tert-butyl, there is no reaction
In the table 2.4B, the reaction of the occurred. It was observed that the color of
alcohol to the lucas reagent is a the solution after the ethyl alcohol oxidized
substitution reaction where the chloride of was darkish blue, for isopropyl alcohol, it
the zinc chloride was replaced by the was green blue and there was no change
hydroxyl group of the alcohol. in color for the tert-butyl alcohol. It was
still in color orange.
e. Oxidation
Table 2.5A (Oxidation) Oxidation test is used to determine if the
COMPOUN COLOR OF ODOR OF alcohol is in primary and secondary
D SOLUTION SOLUTION alcohol. If oxidation occurs, the orange
solution containing the dichromate ions
Ethyl Alcohol Blue Rubbing turns to a green solution containing

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chromium ions. Primary alcohols such as group. Most secondary alcohol will have a
the ethyl alcohol are expected to turn into positive result. Basically, a visible
an aldehyde or carboxylic acid upon precipitate will form from either a methyl
oxidation reaction while the secondary ketone, ethanol, ethanol or a methyl
alcohols such as isopropyl alcohol are secondary alcohol.
oxidized to ketones. Tertiary alcohols such
as tert-butyl alcohol are not capable of Ethanol is the only primary alcohol to be
oxidation because it does not have a have an iodoform reaction because it has
hydrogen. hydrogen in the R group. Then, tertiary
alcohols will not have a reaction because it
f. Iodoform Test does not contain a hydrogen atom
Table 2.6A (Iodoform Test) attached to the carbon with the hydroxyl
group.
COMPOUN OBSERVATION
D g. Bromine Water
Ethyl Alcohol Yellow precipitate formed Table 2.7A (Reaction of the compound with
the saturated bromine water)
Isopropyl Yellow precipitate formed
alcohol COMPOUN OBSERVATION
D

Table 2.6B (Reaction involved) Phenol White precipitate formed

REACTIONS INVOLVED Benzyl Color between yellow,

alcohol orange and brown
Ethyl alcohol

Table 2.7B (Reaction involved)

REACTIONS INVOLVED
Isopropyl alcohol Phenol and saturated bromine water

Based from table 2.6A, both test

compounds, ethyl alcohol and isopropyl Benzyl alcohol and saturated bromine
alcohol had yellow precipitate formed in water
the iodoform test.

Iodoform test is used to identify secondary

alcohols that have a methyl group next to
the carbon bearing the hydroxyl group.
The test is positive when pale yellow
precipitate of triiodomethane (iodoform)
was observed. The test will be positive if Based from table 2.7A, the phenol reacted
the R group is a hydrogen or hydrocarbon with the saturated bromine water which
group or if it is a di-ortho substituted aryl results to a formation of white precipitate

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while the benzyl alcohol did not react with phenol in the sample. So since benzyl
the bromine water because there was only alcohol is not a phenol, then there is no
a color between yellow, orange and brown. change in color.

Bromine water test is a test to identify

activated aromatic rings. Phenol is a CONCLUSIONS AND
RECOMMENDATIONS
strong activator while benzyl alcohol is a
moderate deactivator. This explains the
The objective of this experiment was
formation of white precipitate in the
achieved. The properties of alcohols and
phenol after it was reacted with the
phenols were examined and differentiated
bromine water.
through several tests, and also, the
characteristic reactions of alcohols and
h. FeCl3 Test
phenols were visualized.
Table 2.8A (Reaction of the compound with
FeCl3 solution) Several chemical tests were used to
analyze the hydroxyl group which is
COMPOUN OBSERVATION present in alcohols such as the acid-base
D reaction, reaction with acetyl chloride,
lucas test, oxidation reaction and iodoform
Phenol Turned greenish black
test. Through these test, the classification
Benzyl Turned yellow of alcohols as primary, secondary or
alcohol tertiary alcohol were determined. For
determining the presence of phenol in the
sample, the bromine water test and ferric
Table 2.8B (Reaction involved)
chloride test were used.
REACTIONS INVOLVED
Solubility test among alcohol was also
Phenol and FeCl3 solution executed. Only Benzyl alcohol and
Phenol are insoluble in water and they
are both classified as large alcohols
Benzyl alcohol and FeCl3 solution because they contain more than 6
carbon. Solubility of an alcohol varies
with hydrocarbon chain. As the number
of carbon increases, solubility in water
decreases due to the carbon chain that
repels the water.
Based from table 2.8A, the phenol solution
turned greenish black while in the benzyl The acidity or basicity of the phenol and
alcohol, there was no change in color after ethyl alcohol was determined. Phenols
the addition of ferric chloride. tends to be more acidic than ethyl alcohol.
Acidity of an alcohol varies with the
The ferric chloride test is used to stability of the conjugate base of an
determine the presence or absence of alcohol. Increasing the stability of the
phenols. A positive results gives an intense conjugate base of an alcohol, increase the
color ranging from purple to reddish brown acidity of an alcohol. The conjugate base
to green. This indicates the presence of of phenol (phenolate) is more stable than

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the conjugate base of ethyl alcohol In iodoform test, ethyl alcohol and
(alkoxide) due to resonance therefore isopropyl alcohol had yellow precipitate
phenol is more acidic. formed. This test is to identify secondary
alcohols that have a methyl group next to
In acid-base reaction, the rate of reaction the carbon bearing the hydroxyl group.
depends on the structure of the alcohol. Tertiary alcohols will not have a reaction
Primary alcohol is more favored, followed because it does not contain a hydrogen
atom attached to the carbon with the
by secondary alcohol and tertiary alcohol.
hydroxyl group.
That was the reason why n-butyl and
phenol react completely with the sodium in In bromine water test, the phenol formed a
the experiment. white precipitate while in benzyl alcohol,
there was no change in color. This test is
In reaction with acetyl chloride, phenol and to identify activated aromatic rings. Phenol
ethanol exhibits a top layer formation. This is a strong activator while benzyl alcohol is
formation indicates that the compound a moderate deactivator. This explains the
turned into ester. Esters are formed when formation of white precipitate in the
acetyl chloride reacts with a primary or phenol after it was reacted with the
secondary alcohol. And, alkyl halide are bromine water.
formed when a tertiary alcohol reacts to
acetyl chloride In ferric chloride test, phenol turned
greenish black while in the benzyl alcohol,
In Lucas test, the type of alcohol based on there was no change in color after the
the time taken to form a turbid solution or addition of ferric chloride. This test is used
precipitate with the lucas reagent was to determine the presence or absence of
phenols.
determined. No visible reaction in n-butyl
alcohol. Sec-butyl alcohol exhibited cloudy
For the experiment to go smoothly, it is
solution after seven minutes. While tert- recommended to strictly follow
butyl alcohol exhibited cloudy solution and precautions and instructions in doing the
formation of two layers. Tert-butyl alcohol experiment so that the objectives of the
undergo the most stable reaction while the experiment will be achieved.
n-butyl alcohol undergo the least stable
reaction because of increasing stability of
their carbocation.
REFERENCES
In oxidation reaction, the ethyl alcohol and
isopropyl alcohol are oxidized to carboxylic 1. Klein, D. (2012) Organic
acid and ketone respectively while in the Chemistry. John Wiley &Sons, Inc. NY,
tert-butyl, there is no reaction occurred. America.
Oxidation test is used to determine if the
alcohol is in primary and secondary 2. Baluyut, J. & De Castro K.
alcohol. If oxidation occurs, the orange Oragnic Laboratory Manual.
solution containing the dichromate ions
turns to a green solution containing 3 “Ferric Chloride — Pyridine Test
chromium ions. Tertiary alcohols such as Page". Chemistry.ccsu.edu.
Retrieved 2013-09-11.
tert-butyl alcohol are not capable of
oxidation because it does not have a
hydrogen.

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4 Lucas, H. J. (1930). "A New Test

for Distinguishing the Primary, Secondary
and Tertiary Saturated Alcohols". Journal of
the American Chemical Society 52 (2):
802–804.doi:10.1021/ja01365a053

5 Shriner, R. L.; Fuson, R. C.

(1956). The Systematic Identification of
Organic Compounds (5th ed.). New York:
John Wiley. pp. 117–119.

6 March, Jerry (1985), Advanced

Organic Chemistry: Reactions,
Mechanisms, and Structure (3rd ed.), New
York: Wiley,

7 "The Systematic Identification of

Organic Compounds" R.L. Shriner, C.K.F.
Hermann, T.C. Morrill, D.Y. Curtin, and R.C.
Fuson John Wiley & Sons,

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