Mapua Institute of Technology

School of Chemical Engineering and Chemistry

Chm143L

Organic Chemistry 2 Laboratory Report

Members: Student Number Program

Barangan, David Brian 2015100814 ChE

Dela Cruz, Napoleon Christian E. 2015102616 ChE

Diamante, April Joyce 2015108101 ChE

Dr. Dahlia Apodaca

Professor
 Experiment No. 3

Alcohols and Phenols

ABSTRACT:

Alcohols and Phenols are polar compounds that exhibit dipole moments due to the
electron negative effect of Oxygen and because of that it is always miscible with water since
water is polar and “like dissolves like”. Alcohols are classified to be primary, secondary and
tertiary and there are several tests that can be used to identify what kind of alcohol is your
compound such as Lucas test, Sodium metal test, Ferric Chloride Test, Bromine Water Test,
Iodoform Test, Bromine Test, and Oxidation test. Alcohols also exhibit acidity and there are
factors that affect the acidity of alcohol such as the resonance, induction, orbitals and the
solvating effects. Tertiary alcohols form stable carbo-cations and because of that tertiary alcohols
have a higher rate of completing the reaction.

INTRODUCTION:

Numerous test was performed in this experiment to characterized alcohols and phenols with
different type of structures. Alcohols and phenols are organic compounds that has a hydroxide as
its main functional group, these compounds have been used for good and bad reasons for a very
long time. The first part of the experiment involves testing the solubility of different types of
alcohol and a phenol, were the test compounds mixture with water appear with no cloudiness.
The second part of the experiment involves eight test to differentiate alcohols from phenols or
vice versa, and these test are acidity/basicity, reaction with sodium, reaction with acetyl chloride,
Lucas test, oxidation, iodoform test, bromine water, and finally FeCl3 Test. There are many good
reasons alcohols and phenols have been useful to us; a good reason is that these compounds in
pure or diluted form have been used for medical purposes to disinfect or kill germs, another
reason is that they are used as fuels to power cars and help produce energy for electricity, and
infamously alcohols are founded obviously at alcoholic drinks which is enjoyable to drink as it
relieves stress but if consumed gets a person drunk.
EXPERIMENTAL:

Methodology

This experiment is divided into two parts namely solubility test and other tests
that aim to examine the properties of both alcohols and phenols. The solubility test for the first
part requires 0.5 mL or 0.5 g of ethyl alcohol, n-butyl alcohol, sec-butyl alcohol, tert-butyl
alcohol, benzyl alcohol, glycerol, and phenol to be placed in their respective test tubes. 1 mL of
water is to be added in each test tube. Shaking the test tube is necessary in order to ensure proper
distribution of solute in the mixture. If homogeneous mixture is not yet obtained, 2 mL of water
is to be added. The compound is determined to be soluble only if no cloudiness is observed after
adding 2 mL of water.

The acidity and basicity of ethyl alcohol and phenol is to be determined using
litmus paper and pH paper. The litmus paper determines whether the compound is basic or not
while the pH paper determines the pH value. N-butyl alcohol, sec-butyl alcohol, tert-butyl
alcohol, and phenol are subjected to sodium metal reaction. A small pellet of sodium is to be
added to 2 mL or 0.5 g of the test compound. The lighted splinter is placed on top of the test tube
in order to determine the evolution of hydrogen gas. The reaction between ethyl alcohol and
acetyl chloride shall be observed by adding 3-4 drops of acetyl chloride to 5 drops of ethyl
alcohol or phenol. It has been mentioned in the introduction that only secondary and tertiary
alcohols react with Lucas reagent. This confirms the class of n-butyl alcohol, sec-butyl alcohol,
and tert-butyl alcohol. Oxidation is executed by adding 10 drops of dilute H 2SO4 and 2 drops of
10 % K2Cr2O7 solution to 5 drops of test compound. Oxidation is used to determine or verify
which of the compounds are tertiary alcohols since they are the ones that cannot be oxidized;
hence, it is hypothesized that no reaction will occur. Iodoform test is completed by adding 5
drops of 4M NaOH in 5 drops of ethyl alcohol with 1 mL of water. Iodine in potassium iodide is
to be added dropwise until a yellow color is produced. The mixture is to be heated by placing it
in a warm bath of 60 ˚C for 5-15 minutes. A secondary alcohol with a methyl group attached to
its carbon will be distinguished if a yellow precipitate forms upon heating. Bromine test verifies
the presence of phenol in a compound. This test is established by adding saturated bromine
water, dropwise, to 1 mL water that contains dissolved phenol crystals or benzyl alcohol. This
verifies the positive reaction of phenol to bromine. In addition, FeCl 3 test may be used to
distinguish phenols from other compounds since a color is expected to be produced upon the
addition of 5 drops of 10% FeCl 3 to 3 drops of phenol. This procedure is repeated using benzyl
alcohol. The results and observations in all tests shall be recorded and interpreted afterwards.

RESULTS AND DISCUSSION

I. Solubility

Compound Soluble Insoluble

Ethyl alcohol /
N-butyl alcohol /
Sec-butyl alcohol /
Tert-butyl alcohol /
Benzyl alcohol /
Glycerol /
Phenol /

Alcohols contain an OH- group and because of that alcohol exhibit a dipole
moment. When a compound produces a dipole moment it is classified as a polar
compound, the electron negativity factor of the oxygen contributes to the polar
characteristics of alcohols. Water is the same which also exhibit a polar characteristic
due to its bent molecular geometry and the electron negativity of oxygen which
produces a dipole moment. A solubility test of alcohol is performed using water,
applying “like dissolves like” theoretically it will dissolve due to the polarity of both
compounds. The data shows that Benzyl alcohol and is insoluble, but it is soluble in
water but because of the benzene ring that is the parent chain of benzyl alcohol its
molar mass is high and it will dissolve slowly in water as the mixture is shook well
and most likely the error is that the mixture is not shook well.

II. Test for Alcohol and Phenol

a.) Acidity/Basicity
Compound Rxn w/ Litmus Rxn with pH paper Literature Value
Paper
Ethyl Alcohol Neutral Color change 5
Phenol red Color change 3

Alcohol and Phenols are compared due to their acidity, there are several factors
that affect the acidity of alcohols. First is the Resonance mainly on the double bonds
that is present in the structure, Induction are substrates that has a high electron
negativity, Orbitals exhibit an overlapping of sp2 orbitals which mainly shows a triple
bond on the structure. Ethyl alcohol is a straight chain structured that has a OH group
at carbon 1, while phenol has a parent chain of benzene and has a substrate OH group,
comparing these two compounds Phenol has a resonance factor due to the double
bonds in the benzene ring and because of that phenol will be more acidic and in the
data shown it is evident that Phenol will have a lower value of pH and its reaction
with litmus paper turned out to acidic.
b.) Reaction with Sodium
Compound Observation
n-butyl alcohol Produced gas, colorless, bubbles, turned
yellow
Sec-butyl alcohol Produced gas, colorless, precipitate,
turned pale yellow
Tert-butyl alcohol Produced gas, precipitate, pale yellow,
bubbles
Phenol Produced gas, precipitate, bubbles,
colorless

One method for determining an alcohol is through the addition of a sodium metal
in which the chemical reaction states that it will produce a hydrogen gas and because
of that when determining a compound if it is an alcohol or not, one indicator is using
a sodium metal, if bubbles are produced in the container as the sodium metal
dissolves then it is safe to assume that it is an alcohol. Tertiary alcohols are highly
reactive since it produces the most stable carbo-cations, when sodium metal is added
in Tert-Butyl alcohol it immediately reacted and bubbles are produced immediately
meaning hydrogen gas evolved immediately and alkoxide is produced in the reaction.

c.) Reaction to Acetyl Chloride

Compound Observation
Ethyl Alcohol Produced gas, colorless
Phenol Produced gas, colorless, formed
precipitate(white)

Ethyl alcohol reacts with acetyl chloride by substituting the Cl group on the acetyl
chloride with the alcohol group and the hydrogen bonded will be removed and will be
bonded on the Cl atom, thus HCl will be formed from the reaction of alcohol and
acetyl chloride. This method is used to form an ester from an alcohol but usually
needs heat and a catalyst to have a satisfying conversion rate.

d.) Lucas Test

Compound Observation
n-butyl alcohol No reaction was observed, clear
mixture
Sec-butyl alcohol After five minutes, reaction was
indicated by cloudiness
Tert-butyl alcohol After two minutes, reaction was
indicated by cloudiness

For this table the reaction rate was compared and since tertiary alcohols
form stable carbo-cations they have a higher rate of completing the reaction, it is
evident in the table the tert-butyl alcohol immediately the reaction with the Lucas
reagent since it is an example of an tertiary alcohol. The Lucas reagents uses Zinc
Chloride and hydrochloric acid so that water will form and the Cl- atom will
substitute the OH group in the compound.
e.) Oxidation

Compound Color of Solution Odor of Solution

Ethyl Alcohol Dark blue Pungent
Isopropyl Alcohol Dark blue Pungent
Tert-Butyl Alcohol Orange Less pungent

Oxidation is usually used to determine what type of alcohol is the

compound. Primary, secondary and tertiary alcohols are identified by the
oxidation tests in which primary alcohols form carboxylic acids, secondary
alcohols form ketones while tertiary alcohols do not react with oxidation tests
because there is no hydrogen available. It is evident in the data that Tert-butyl
alcohol did not react since there is no change in color when potassium dichromate
is added, there is no color change nor the odor did not change at all.

f.) Iodoform Test

Compound Observation
Ethyl Alcohol Clear liquid, yellow precipitate
Isopropyl Alcohol Cloudy liquid, yellow precipitate
 The iodoform test reacts only in primary and secondary alcohols since
there are available hydrogens for the reaction to take place in but tertiary alcohols
do not react since there is no hydrogen available. Ethyl alcohol is a primary and
thus forming a precipitate and Isopropyl alcohol is a secondary alcohol and thus
forming a precipitate and the reaction proceeds spontaneously.

g.) Bromine Test

Compound Observation
Phenol clear liquid, white orange precipitate
Benzyl alcohol Cloudy liquid, orange liquid (formed at
the bottom)

Phenols reacted easily with the Bromine Test because of the OH group
that is an activator, an electrophilic aromatic substitution will occur on the phenol
while for the benzyl alcohol does not contain a free hydrogen in which bromine
will not substitute, it is evident in the data that the benzyl alcohol did not react
since it formed a layer.

h.) FeCl3 Test

Compound Observation
Phenol Turned dark
Benzyl Alcohol Formation of layer

Ferric Chloride test occur mostly on enols in which alcohol group or the
OH group is attached to a double-bonded carbon one example is the benzene ring
which is composed of 6 pi electrons and has 3 double bonds present, one OH
group is attached to that ring. Phenols would mostly react with iron and form
complexes, the precipitates that will form will range from purple to red to orange.
Primary, secondary, and tertiary would not react because there is no enol present.
In the data given Benzyl alcohol did not react because it is a primary alcohol and
it not an enol. So basically, phenols are mainly identified by this test.

CONCLUSION

Alcohols are straight chain organic compounds that have –OH group as a substituent
while phenols are aromatic rings that exhibit –OH substituent. This experiment utilized solubility
test, acidity, reaction with sodium, reaction with acetyl chloride, Lucas test, oxidation, iodoform
test, bromine water test, and FeCl3 test. It was verified that alcohols are soluble in water since
they are considered to be polar compounds. By pH paper test, it was determined that phenols are
much more acidic than alcohols because of the greater amount of resonance structures it has.
Sodium metal reacts with tertiary alcohols; hence, it was expected for tert-butyl alcohol to react
at a faster rate compared to n-butyl alcohol. This test determines the class of alcohols whether
they are tertiary, secondary, or primary. Another test which may be used to classify alcohols is
the acetyl chloride test. This test proceeds only for primary and secondary alcohols. Both ethyl
alcohol and phenol seem to proceed with this test indicating that either of them may be primary
or secondary. Lucas test reacts faster with tertiary alcohols and slower with primary alcohols.
The class of alcohols used as test compounds were verified by this test where tert-butyl alchohol
had a faster rate of reaction upon the addition of Lucas reagent. Oxidation and iodoform tests
proceed with primary and secondary alcohols. Ethyl alcohol, being a primary alcohol, and
isopropyl alcohol, being a secondary alcohol, had a color change upon the addition of potassium
dichromate. This indicated a completion of reaction. The results in oxidation were verified in
iodoform test wherein yellow precipitate implies a positive result. Positive result was obtained
for ethyl alchohol and isopropyl alcohol in this test. Phenols were expected to react faster in
bromine test as compared to benzyl alcohol due to the activating substituent –OH making the
benzene ring highly reactive. Ferric chloride test is a useful test in distinguishing phenols since
this test only indicates the presence of enols. It was seen in the experiment that benzyl alcohol
did not react with ferric chloride; this is expected since no enols are found in the structure of
benzyl alcohol.

REFERENCES

 Wade, L. G. (2011, December 02). Alcohol. Retrieved February 17, 2017, from
https://www.britannica.com/science/alcohol

 Alcohols. (n.d.). Retrieved February 17, 2017, from http://www.scienceclarified.com/A-

Al/Alcohols.html