Cagatan, Jay Marie B.

BSN

Experiment 6

Properties of Alcohols and Phenols

I. Introduction

The functional group OH is composed of alcohols and phenols. The OH group in a

phenol is linked to a carbon on a benzene ring where the OH group is linked to an sp3
hybridized carbon atom as in alcohols. Depending on the number of carbon atoms bound
to the carbon bearing OH group, alcohols are graded as principal, secondary and tertiary.
The following are representative examples of phenol and three forms of alcohol.

Although the functional group OH is included in these four groups of compounds, the
unique qualities differences in their reaction chemistry allow one to easily distinguish one
from the other. Phenols are more acidic than spirits. A variety of commercial, medicinal,
and even household applications are found for alcohols as well as phenols. Alcohol and
phenol derivatives are used in medications, alcohol is used as popular industrial solvents,
etc.

In this experiment it will subject a series of ways to identify three classes of the alcohols,
properties of alcohols and phenols and distinguish between alcohols and phenols. The
data will be presented in a tabular form showing the test was done and its result and
remarks.

II. Objectives:

At the end of the experiment, the students should be able to:

1. To use the chemical characteristics to differentiate phenols and the three

types of alcohols
2. To learn characteristic chemical reactions of alcohols and phenols
 III. Apparatus& Chemicals

Chemicals Apparatus
Ethanol Test Tube rack
2-Propanol Test Tube
2-methyl-2-propanol Pipette
Cyclohexanol Beaker
Salicylic Acid Spatula
Red Food Dye Glass rod
Lucas reagent (ZnCl2)
Acidic Dichromate solution (Cr6+)
Ferric Chloride solution (FeCl3)
Bromine Solution

IV. Procedures

I. Physical Properties of Alcohol

Alcohols in Water

1. Clean and dry test tubes are labeled as Water, Ethanol, 2-Propanol, 2-methyl-2-
propanol, cyclohexanol, and salicylic acid.
2. Ten drops of each alcohol are placed into its corresponding test tube and then added
1-2 ml of water to each test tube. Record your observation on the data sheet.

Alcohols in Hexane

1. Six clean test tubes are prepared and labeled and dropped a sample of alcohol into its
corresponding test tube with a sample of alcohol into its corresponding test tube.
2. Then 1-2 ml of hexane was added to each of the test tubes and observations were
recorded in a data sheet.

II. Chemical Properties of Alcohols

Lucas Test

1. In an appropriate test tube, 5 drops of each sample were placed and then added 1 ml
of Lucas reagent. Then a cork was used as a stopper.
 2. Then the chemicals are mixed vigorously by holding the top of the tube with the
thumb and index finger of one hand and striking the bottom of the tube horizontally
with the index finger of the other hand.
3. After the contents are mixed, the cork are removed and letting the tube settle for five
minutes.
4. Cloudiness or separation of a second layer are visible in a five minute time span.

Oxidation by Chromic Acid Test

1. Started with placing 5 drops of 1ml of pure acetone in each sample in a test tube.
2. In each test tube, 1 small drop of jones reagent (CrO3) was added.
3. Then a positive test is marked by the formation of a green color within 15 seconds
upon the addition of the orange-yellow reagent to a primary or secondary alcohol.

Ferric Chloride Test

1. Added 5 drops of each sample to a clean and dry and then the test tubes are labeled
to be tested.
2. Added 2 drops of ferric chloride solution into each test tube and the observations
were recorded.

Acidity of Phenol

1. First is to mix 1 ml of 2% solution of phenol with 1 ml of sodium carbonate solution.

2. Using a 1% solution of acetic acid and 1- butanol the test were repeated using 2
separate test tubes instead of phenol as the acid.
3. Then 1 ml of sodium carbonate was added to the solution on each test tubes.
4. The acidity of phenol to acetic acid and 1-butanol are compared base on the rate of
reaction with sodium carbonate solution and accounted for some differences.

V. Data & Results

I. Physical Property

Experiment Sample 1 Sample 2 Sample 3 Sample 4

(Ethanol) (2-Propanol) (1-Pentanol) (Phenol)
Solubility in H2O Miscible Miscible Immiscible Immiscible
Solubility in C6H14 Immiscible Miscible Miscible Miscible
II. Chemical Properties:

A. Lucas Test:

Relative Ease of
Substitution
Alcohol + Concentrated HCl Description
(slow, moderate, or
fast)
React so slowly
that no change in
a. Primary Alcohol Used
the appearance Very slow or no
of the solution at reaction at all.
(Propan-1-ol)
room
temperature.
Takes several
b. Secondary Alcohol Used
minutes until the
Slow
solution
(Propan-2-ol)
becomes cloudy.
The solution
c. Tertiary Alcohol Used turns turbid Fast
immediately
(2-Methylpropan-2-ol) upon mixing the
reactans.
Chemical Equations:
a. Propan-1-ol with hydrochloric acid C3H8O
b. Propan-2-ol with hydrochloride CH3CHOHCH3
acid

c. 2-Methylpropan-2-ol with C4H10

hydrochloric acid

B. Chromic Acid Test:

Alcohol + H2CrO4 Description Relative Ease of Oxidation

a. Primary Alcohol Used The solution turns from Primary alcohol can oxidized into
orange to green. After 5 an aldehyde which can further
(Ethanol) minutes it turns to blue. oxidized into a carboxylic acid.
b. Secondary Alcohol Used The solution turns from Secondary alcohol can oxidized
orange to green. After 5 into a ketone.
(2-Propanol)
 minutes it turns to blue.

c. Tertiary Alcohol Used There are no reactions.

Tertiary alcohol will not undergo
oxidation.
(2-Methyl-2-propanol)
Chemical Equations:
a. Ethanol C2H5OH
b. 2-Propanol CH3CHOHCH3
c. 2-Methyl-2-propanol (CH3)3COH

C. Ferric Chloride Test:

Alcohols Description (- or +)
a. Primary Alcohol Used Negative, it does not react with ferric chloride
solution and remains dark-yellow
(Ethanol)
b. Secondary Alcohol Used Negative, it does not react with ferric chloride
solution and remains dark-yellow
(2-Propanol)
c. Tertiary Alcohol Used Negative, it does not react with ferric chloride
solution and remains dark-yellow
(2-Methyl-2-propanol)

D. Relative Acidity of Phenol

Chem. Family/Name of Compound Tested Description

a. Phenol (Sulfuric Acid) Slow reaction, creates a white

precipitate and pH level is 4.
b. Alcohol Used (Ethanol) Acidic and pH level reaches 7.
c. Carboxylic Acid Used (Sodium Hydroxide) The solution is colorless.
Chemical Equations:
a. Phenol H2SO4
(Sulfuric Acid)

b. Alcohol Used C2H5OH

(Ethanol)

c. Carboxylic Acid NaOH

 Used
(Sodium
Hydroxide)

VI. Analysis

A. Physical Properties

Alcohols are organic molecules that contain a hydroxyl (-OH) group. Phenols are molecules that
contain an –OH group that is directly attached to a benzene ring.

Alcohols can be classified as primary, secondary, or tertiary. This classification is based on

whether the alcohol carbon is attached to one, two, or three alkyl groups. This classification is
important, because the different classes of alcohols react differently.

Because alcohols contain an –OH group, they are able to form hydrogen bonds to one another.
They therefore have high boiling points. Alcohols can also form hydrogen bonds with water, so
small alcohols are water-soluble. The smallest alcohols, methanol (CH3OH) and ethanol
(CH3CH2OH), are completely soluble in water in any proportions. As the hydrocarbon part of an
alcohol gets larger, the alcohol becomes less water soluble and more soluble in nonpolar
solvents.

Alcohols are soluble in water because they form intermolecular hydrogen bonding with water
molecules. The solubility decreases with increase in mass because the hydrocarbon part becomes
larger and resists the formation of hydrogen bonds with water molecules.

The solubility of isomeric alcohols increases with branching because the surface area of the
hydrocarbon part decreases with branching.

Phenol is somewhat soluble in water. It acts as a weak acid in water, so a solution of phenol will
be slightly acidic. Phenols also form hydrogen bonds with water and hence are soluble in water.
However, the solubility of phenols is much lower than that of alcohols due to the presence of the
larger hydrocarbon part (benzene ring).

B. Chemical Properties

Lucas Test

Some alcohols react with ZnCl2 in an acidic aqueous solution to give an alkyl choride. The
Lucas test involves a substitution reaction, where the –OH group of the alcohol is replaced by a
Cl atom. The Lucas reagent consists of a mixture of HCl and ZnCl2 that are dissolved in water.
The mechanism of this reaction involves a carbocation intermediate: first an OH- ion is removed
from the alcohol, leaving the carbon atom in the molecule positively charged. Then a Cl- ion
adds to the positively charged carbon atom. The result is the alcohol is converted to a chlorinated
alkane, with the Cl occupying the spot that the –OH was in. Since tertiary carbocations are much
more stable than primary or secondary carbocations, tertiary alcohols will react readily with the
Lucas reagent. Secondary alcohols will react slowly (usually in 5-10 minutes). Primary alcohols
will not react much at all, since a primary carbocation is so unstable. The chlorinated product is
usually insoluble in water (the solvent in this reaction), whereas the initial alcohol is usually
soluble in water because of its –OH group. Cloudiness appearing in the reaction mixture is taken
as evidence of a positive reaction. You will need to note the time at which the cloudiness
appears.

Chromic Acid Test

Alcohols can be oxidized by oxidizing agents such as chromate or dichromate ions (these contain
chromium in the +6 oxidation state). A primary alcohol is oxidized to an aldehyde and then
oxidized further to a carboxylic acid.

Secondary alcohols are oxidized to ketones.

Tertiary alcohols cannot be oxidized.

In the process of oxidation, the orange chromate solution is reduced to a green solution
containing chromium in the +3 oxidation state. During this oxidation, hydrogen atoms are
removed from the alcohol (one hydrogen is removed from the -OH group and the other is
removed from the carbon atom that is attached to the –OH group). Tertiary alcohols cannot be
oxidized because there is no hydrogen atom attached to the alcohol carbon.

In this test, if the orange solution of chromate turns green, it is taken as evidence that oxidation
has occurred. If the substance tested is an unknown alcohol or phenol and you see a positive
reaction, it means that it cannot be a tertiary alcohol. Phenols can also be oxidized, but they are
not oxidized to aldehydes or ketones.

Ferric Chloride Test

Phenols react with FeCl3 to form a colored complex with the Fe3+ ion. The color varies from
purple to orange depending on the structure of the phenol tested. Alcohols do not form colored
complexes with iron ion. In this test, the appearance of a color is taken as a positive test and it
indicates that a phenol was present in the original solution.

Relative Acidity of Phenol

Phenol is a very weak acid and the position of equilibrium lies well to the left. Phenol can lose a
hydrogen ion because the phenoxide ion formed is stabilised to some extent. The negative charge
on the oxygen atom is delocalised around the ring. The more stable the ion is, the more likely it
is to form. One of the lone pairs on the oxygen atom overlaps with the delocalised electrons on
the benzene ring.

This overlap leads to a delocalization which extends from the ring out over the oxygen atom. As
a result, the negative charge is no longer entirely localized on the oxygen, but is spread out
around the whole ion.

Spreading the charge around makes the ion more stable than it would be if all the charge
remained on the oxygen. However, oxygen is the most electronegative element in the ion and the
delocalized electrons will be drawn towards it. That means that there will still be a lot of charge
around the oxygen which will tend to attract the hydrogen ion back again. That is why phenol is
only a very weak acid.
VII. QUESTIONS:

1. Write the complete balanced reaction for the combustion of the following alcohols:

Methanol: CH3OH + O2→ 2CH3OH + O2 ——> 2CO2 + 4H2O

Butanol: C4H9OH + O2 → C4H9OH + 6O2 ——> 4CO2 + 5H2O

2. Write equations, including structures, for the reactant alcohol and any product you would
produce when each of these alcohols is treated with the oxidizing agent, chromic acid:

Oxidation of ethyl alcohol:

When ethanol is reacted with chromic acid, the alcohol groups in ethanol are converted to
carboxylic acid and functional groups. Ethanol has only one carbon-oxygen bond, but in
the product, there is a new oxygen atom and a new carbon-oxygen double bond. The
product of an ethanol oxidation is a compound know as acetic acid.

Oxidation of isopropyl alcohol:

The oxidation of isopropyl alcohol by chromic acid is a reaction first order with respect
to the acid chromate ion, HCrO4-, first order with respect to the alcohol, and second
order with respect to hydrogen ion. Isopropyl alcohol is oxidized to form acetone by
alcohol

dehydrogenase in the liver, and has a biological half-life in humans between 2.5 and 8.0
hours.
 Oxidation of t-butyl alcohol:

There is no reaction because there is no hydrogen to the alpha carbon.

3. When alcohols react with acids, esters are produced. Many esters have pleasant odors.
Show the reaction, and structure of the product when each of the following alcohols
react:

Ethyl alcohol with glacial acetic acid to produce ethyl acetate (what does it smell
like?)

The colorless liquid has a characteristic sweet smell same as a pear drops. It is usually
used in glues, nail polish removers, and in the decaffeination process of tea and coffe.
Ethyl acetate is the ester of ethanol and acetic acid.

Isoamyl alcohol (isopentyl) with glacial acetic acid to produce isoamyl (isopentyl)
acetate (what does it smell like?)

Isoamyl acetate has a strong odor which is described as similar to both banana and pear.
 Salicylic acid with methanol acid to produce methyl salicylic acid (what does it smell
like?)

Methyl salicylate is an organic ester responsible for the minty smell of wintergreen.

4. Show the step-by-step reaction products, and names, when ethanol is oxidized. You will
produce an aldehyde, which also ends up reacting.

Ethanol is oxidised by acidified sodium dichromate in a test tube reaction, firstly to form
ethanal (acetaldehyde), and with further oxidation, ethanoic acid (acetic acid).

Procedure:
1. Place about 3 cm3 of acidified sodium dichromate solution in a boiling tube.
2. Use a teat pipette to add 5–7 drops of ethanol, with shaking.
3. Cool the mixture in the tube under a tap. Note the sweetish smell of ethanal
(acetaldehyde) at first, then becoming sharper as oxidation continues and forms
ethanoic acid (acetic acid).
4. When the reaction has subsided, the mixture can be warmed gently; the smell of
ethanoic acid will become more noticeable.

The colour of the solution turns from orange to blue-green as the dichromate(VI) ion,
Cr2O72-, is reduced to the chromium(III) ion, Cr3+. Note that the sodium dichromate
solution is more concentrated than 0.2 mol dm-3, so the toxicity level is high. A more
dilute solution can be used if preferred, with longer reaction time, the mixture may need
gentle heating in a water bath.

Ball and stick molecular models will be useful for modelling both stages of the reaction
scheme.

Students could be asked to write equations for the reactions involved when ethanol is
oxidised by sodium dichromate in acid solution to (i) ethanal (ii) ethanoic acid, using [O]
to represent oxygen coming from the dichromate.

A variant on this experiment as a demonstration for advanced students is to place four

petri dishes on an overhead projector, and pour the same volume of acidified sodium
dichromate solution into each dish. Then add 1 cm3 of 3 different alcohols, one to each
dish (leave the fourth dish is a control), and observe the different rates of oxidation from
the rate of the colour change. This approach can be used to investigate the effect of chain
 length of primary alcohols, or the differences between the reactions of oxidising agents
with primary, secondary and tertiary alcohols.

VIII. Conclusion

On this experiment, several tests were used to analyze the hydroxyl group, the functional group
found in alcohols. Alcohols were identified as primary, secondary or tertiary according to the
tests performed.The first test conducted is the solubility test where water is the solvent. Test
compounds used were ethanol, 2-propanol, 1-pentanol, and phenol.There are also tests
performed to differentiate alcohols from phenols and also its chemical properties. These were
lucas test, chromic acid test, ferric chloride test and relative acidity of phenol. The objectives of
this experiment were met which were to examine and differentiate the properties of alcohols and
phenols and to visualize the characteristic reactions of alcohols and phenols. It can be
recommended that the reactions must be observed for a longer period of time since the other
reactions were not totally completed. It can be recommended that reactions can be performed
only if the reagents used are free from any contaminations. These can be done by performing the
experiment under the fumehood and avoiding exposure to air. Any reactions using contaminated
reagents will induce erroneous result.

IX. References

VIDEOS

https://youtu.be/au_fwcaVA8Q
https://youtu.be/OQF8Aiv1OZQ
https://youtu.be/4yPjkRLcauI
https://youtu.be/bkVOn_7j7-I
https://youtu.be/TxNGhiil8aw
https://youtu.be/Y6Zl3zuNYu4
https://youtu.be/NOVkLMrw2ls

SOURCES

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https://byjus.com/chemistry/phenol-acidity/

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http://employees.oneonta.edu/knauerbr/chem226/226expts/226_expt08_pro.pdf

(n.d). Retrieved from

https://www.angelo.edu/faculty/kboudrea/index_2353/Chapter_03_2SPP.pdf

(n.d). Retrieved from

https://laney.edu/cheli-fossum/wp-content/uploads/sites/210/2012/01/6-Alcohols-and-
Phenols.pdf
(n.d). Retrieved from
https://guides.hostos.cuny.edu/che120/chapter2

(n.d). Retrieved from

http://www.chem.latech.edu/~deddy/chem121/Alcohols.htm

(n.d). Retrieved from

http://www6.grafton.k12.wi.us/ghs/teacher/mstaude/APcalendar/documents/IdofAlcohols.doc

X. Documentation

Solubility in Water Solubility in Hexane

 Lucas Test Chromic Acid Test

Ferric Chloride Test Properties of Phenol in Warm Water

Properties of Phenols. Relative Acidity of Phenols