INTRODUCTION

The specific group of atoms bonded in the organic molecule will determine certain
physical and chemical characteristics to the molecule as a whole. [1] These groups are known as
functional group. The parent chain of the organic molecule can affect the characteristics of
functional group.
The functional group OH bonded in the organic molecule is called alcohol. In alcohols
the -OH group is attached to a tetrahedral carbon atom. If the carbon that is bonded to the -OH is
bonded to one carbon and two hydrogens, the alcohol is a primary (1o) alcohol.

If the carbon that is bonded to the -OH is bonded to two carbons and one hydrogen, the alcohol is
a secondary (2o) alcohol.

If the carbon that is bonded to the -OH is bonded to three carbons, the alcohol is a tertiary (3 o)
alcohol.[2]

All of these alcohols share some characteristics but other characteristics are different
owing to their different structures. Several tests that involved a chemical reaction can be carried
out in order to distinguish the chemical properties among the three classes of alcohols such as
Lucas and chromic acid test. Alcohols are very important commercially used nowadays as
solvents, drugs and disinfectants. Methanol or methyl alcohol (CH3OH), ethanol or ethyl alcohol
(CH3CH2OH) and 2-propane or ispprophyl alcohol ((CH 3)2CHOH) are the most widely used
alcohols.[3]

When the hydroxyl group OH is bonded to a benzene ring, it will use the phenol as
parent name. In phenols the -OH group is directly attached to a carbon number 1 that is part of an
aromatic ring.

Alcohols and phenols are similar in some ways but the chemical properties of phenols
can be slightly different from the alcohols even though they have the same hydroxyl group
bonded in the compounds.[4] Iron (III) chloride test is commonly used to distinguish between
alcohol and phenol group because they react differently with the reagent.

AIM
1. To learn characteristic chemical reactions of alcohols and phenols.
2. To use these chemical characteristics for identification of an unknown organic compound.

MATERIALS
1. Aqueous phenol
2. Acetone ( reagent grade)
3. 1-Butanol
4. 2-Butanol
5. 2-Methyl 2-Propanol
6. Chromic acid solution
7. Dioxane
8. Iron (III) chloride solution

9. I2-KI solution
10. Lucas reagent
11. Sodium hydroxide, NaOH solution
12. Unknown A
13. Unknown B
14. Distilled water
15. Gloves
APPARATUS
1. Beaker
2. Test tube
3. Corks
4. Dropper

PROCEDURE
A. Physical Properties of Alcohols and Phenols
1. 10 drops of each sample were dropped into 6 separate test tubes (10013 mm) that
2.
3.
4.
5.

labeled 1-butanol, 2-butanol, 2-methyl-2-propanol, unknown A and unknown B.

Each sample was diluted by mixing with 3 mL of distilled water.
Into a separate test tube, 2mL of prepared water solution of phenol was placed.
The homogeneousness of the solutions was observed.
The pH test was done by dipping a pH paper into each test tube. The value of pH was
read by comparing the color of pH paper to the chart on the dispenser.

B. Chemical Properties of Alcohols and Phenols.

i.

Iodoform test.

1. 6 test tubes (15018 mm) were labeled 1-butanol, 2-butanol, 2-methyl-2-propanol,

unknown A and unknown B.
2. 5 drops of each sample were added into their respective test tube. Then, 2 mL of water
was added to each test tube.
3. If the compound was not soluble, dioxane was dropped until the solution become
homogenous.
4. Next, 2 mL of NaOH solution was added into each test tube and mixed by tapping the test
tube with a finger.

5. The mixture was warmed in a 60

water bath and prepared solution of I2-KI test

reagent was dropped with shaking into each test tube until the solution becomes brown.
6. 6 M of NaOH solution was added by using dropper into each test tube until the solutions
become colorless. The test tubes were kept in the warn water bath for 5 minutes. After 5
minutes, the test tubes were removed from the water bath, letting them cool.
7. The test tubes were put to one side and the observation on any changes in the solutions
was taken when all the other tests are completed.
8. The formation of light yellow precipitate was observed in each test tube whether it
present or absent.
ii.

Lucas Test.
1. 6 test tubes (10013 mm) were labeled 1-butanol, 2-butanol, 2-methyl-2-propanol,
unknown A and unknown B. 5 drops of each sample were added into their respective test
tube.
2. 1 mL of Lucas reagent was added into each test tube. The solutions were mixed well by
stopping each test tube with a cork, tapping the test tube sharply with finger for a few
seconds. The cork was removed after mixing and the test tubes were allowed to stand for
5 minutes.
3. After 5 minutes, any cloudiness formed was carefully observed. After 10 minutes, if the
cloudiness still absent, the test tubes were warmed for 15 minutes in a 60

water

bath.
4. Any cloudiness was observed again.
iii.

Chromic Acid.
1. 6 test tubes (10013 mm) were labeled 1-butanol, 2-butanol, 2-methyl-2-propanol,
unknown A and unknown B. 5 drops of each sample were added into their respective test
tube.

2. To each test tube, 10 drops of reagent grade acetone and 2 drops of chromic acid were
added. The test tube then placed in a 60 water bath for 5 minutes.
3. Any changes in color of the solutions were observed.
iv. Iron (III) Chloride Test.
1. 6 test tubes (10013 mm) were labeled 1-butanol, 2-butanol, 2-methyl-2-propanol,
unknown A and unknown B. 5 drops of each sample were added into their respective test
tube.
2. 2 drops of iron (III) chloride were added to each test tube.
3. Any color changes in each solution was observed and taken.
v. Unknowns.
1. By comparing the observations of the unknowns and the known hydrocarbons, the
unknown A and unknown B were determined.

DATA AND OBSERVATION

i.

Physical Properties of Alcohols and Phenols

SAMPLE
1-butanol
2-butanol
2-methyl-2-propanol
Phenol
Unknown A

SOLUBILITY IN WATER
Soluble
Soluble
Soluble
Soluble
Soluble

pH VALUE
5
5
5
4
5

Unknown B

Soluble

B. Chemical Properties of Alcohols and Phenols.

i.
Iodoform Test.
SAMPLE
1-butanol
2-butanol
2-methyl-2-propanol
Phenol
Unknown A
Unknown B

ii.

Lucas Test.

iii.

SAMPLE
1-butanol
2-butanol
2-methyl-2-propanol
Phenol
Unknown A
Unknown B
Chromic Acid Test.
SAMPLE
1-butanol
2-butanol
2-methyl-2-propanol
Phenol
Unknown A
Unknown B

iv.

OBSERVATION
Remain colourless
Remain colourless
Remain colourless
Remain colourless
Remain colourless
Remain colourless

OBSERVATION
No reaction
No reaction
Turns cloudy immediately
No reaction
No reaction
Turns cloudy immediately

OBSERVATION
Yellow turn to blue-green solution
Yellow turn to blue-green solution
Yellow colour remain unchange
Yellow colour turn to brown
Yellow turn to blue-green solution
Yellow colour remain unchange

Iron (III) Chloride Test.

SAMPLE
1-butanol
2-butanol
2-methyl-2-propanol
Phenol
Unknown A

OBSERVATION
Remain yellow
Remain yellow
Remain yellow
Yellow changes to violet
Remain yellow

Unknown B

Remain yellow

DISCUSSION
A. Physical Properties of Alcohols and Phenols
Solubility in water
In this experiment, when 1-butanol, 2-butanol, 2-methyl-2-propanol and phenol are
diluted by adding distilled water, all these four samples soluble in water. Alcohols and phenol are
really highly soluble in water because of the polar hydroxyl groups OH in the water and
alcohols and phenol can associate one another through the hydrogen bonding.[5]

Acidity of alcohols and phenols

In the pH test of all the aqueous solution, the result showed that all alcohols and phenol
are acidic. The pH value of phenol is 4 while the pH value is 5 for 1-butanol, 2-butanol and 2methyl-2-propanol. The pH value of phenol is slightly more acidic compared to alcohols. This is
because the benzene ring in the phenol stabilized the negative charge of the phenoxide ion
through resonance since benzene ring is considered as electron donor.[6]

B. Chemical Properties of Alcohols and Phenols.

i.
Iodoform test.
Iodoform test is used to identify the presence of CH3CH(OH) group in alcohols.[7]In the
experiment, initially all the samples (1-butanol, 2-butanol, 2-methyl-2-propanol, phenol,
unknown A, unknown B) were mixed with iodoform reagent followed by NaOH solution in 60C

water bath to colourise the brown colour. Then, the samples were let cool in room temperature
for a while before being observed.
The result showed that all the samples remain colourless. However, theoretically 2-butanol
should form a yellow precipitate in iodoform reaction. Thus, it is assumed that there must be an
error while doing the experiment.
For primary alcohol, 1-butanol does not show any reaction with iodine in aqueous sodium
hydroxide. Only ethanol gives the iodoform reaction because it have the part structure
CH3CH(OH). 2-butanol which is secondary alcohol has CH3CH(OH) group that can be oxidized
to form methyl carbonyl compound. This compound in the presence of NaOH reacts with iodine
resulting in the substitution of the hydrogen atoms present on the carbon atom lying adjacent to
the carbonyl group. Tri-iodo methyl carbonyl compound is formed which then reacts with
hydroxide ions to produce carboxylic acid and iodoform (CHI3).[8]

Tri-iodo methyl carbonyl

compound

Iodoform

Carboxylic
acid

The chemical equation for this reaction is :

H

CH3CH2 C CH3 + 4I2 + 6NaOH CH3CH2 C O-Na+ + 5NaI + 5H2O + CHI3(s)

OH
2-butanol

Sodium salt of
carboxylic

iodoform
(yellow precipitate)

Phenol reacts with iodine in aqueous sodium

hydroxide. The chemical equation for this reaction is :

2-methyl-2-propanol which is tertiary alcohol does not have H atom attached to the carbon with
the OH group. Thus it gives a negative result for iodoform reaction.

ii.

Lucas Test.
Lucas test is used to distinguish among primary secondary and tertiary alcohol by

differentiate the rate of reaction of alcohols with Lucas reagent. The Lucas reagent is a solution
of zinc chloride in concentrated hydrochloric acid [9].
When 5 drops of the samples (1-butanol, 2-butanol, 2-methyl-2-propanol, phenol, unknown
A, unknown B) were mixed with 1 mL of Lucas reagent, 2-methyl-2-propanol and unknown B

turn cloudy immediately and the rest showed no reaction. After 10 minutes, test tubes with no
reaction were placed in 60 C water bath for 15 minutes. After 15 minutes, all the samples do not
show any changes. However, theoretically, secondary alcohol which is 2-butanol should turn
cloudy. Thus, it is assumed that there must be an error while doing the experiment. For 1-butanol
and phenol, both should not show any changes.
From the observation, 2-methyl-2-propanol which is tertiary alcohol reacts rapidly (within 1
minute) with Lucas reagent to form alkyl chloride. The chemical reaction involved is substitution
where the OH group of alcohol is replaced by chloride ion from hydrochloric acid, forming
alkyl chloride

[4]

. The cloudiness indicates the formation of alkyl chloride which is insoluble in

aqueous solution. The chemical equation for this reaction is

(CH3)3C-OH (aq) + HCl (aq) + ZnCl2 (aq) (CH)3C-Cl (s) + H2O (l)
2-methyl-2-propanol

2-chloro-2-methylpropane

After 15 minutes in 60 C water bath, 2-butanol which is secondary alcohol should reacts with
Lucas reagent to form alkyl chloride which appears as cloudy mixture. The chemical equation for
this reaction is :
(CH3)2CH2CH-OH (aq) + HCl (aq) + ZnCl2 (aq) (CH3)2CH2CH-Cl (s) + H2O (l)
2-butanol

2-chlorobutane

1-butanol as primary alcohol and phenol does not show any reaction with Lucas reagent even
after 15 minutes in 60 C water bath.
CH3(CH2)2CH2-OH + HCl (aq) + ZnCl2 (aq) No reaction
1-butanol

+ HCl (aq) + ZnCl2 (aq) No reaction

iii.

Chromic Acid Test.

In chromic acid test, these samples were tested to distinguish primary and secondary alcohols

from tertiary alcohols. For 1-butanol and 2-butanol, the yellow colour changed into blue-green
solution. The oxidation state of chromium changed from +6 (yellow colour) to +3 (pale green
colour).
The reaction with chromic acid occurred because these samples are primary and secondary
alcohols. The primary alcohols (1-butanol) oxidized and forming an aldehyde (butanal) as
intermediate and later forming butanoic acid. For secondary alcohol (2-butanol), the oxidation
reaction occurs and forming a ketone (2-butanone).

H2CrO4
Acetone
1-butanol

Butanal (intermediate)

Butanoic acid

Cr2(SO4)3
(blue-green)

H2CrO4
Acetone
2-butanol

+
2-butanone

Cr2(SO4)3
(blue-green)

In the test tube that contained 2-methyl-2-propanol, the yellow colour remains unchanged
because this sample is a tertiary alcohol. Thus, oxidation reaction did not occur.

H2CrO4
No Reaction
Acetone

For phenol, the colour of the solution changed from yellow into brown colour solution.
Due to the structure of phenol that has a ring structure, the oxidation reaction cannot occur to
form either carboxylic acid or ketone.

H2CrO4
No reaction
Phenol

iv.

Acetone

Iron (III) Chloride Test.

When 1-butanol, 2-butanol and 2-methyl-2-propanol are added with iron (III) chloride

solution, the colour of mixture remained yellow. This is because there is no reaction takes place
in these three different test tubes. However, the yellow colour in the solution is showing that the
presence of iron (III) ion in the solution.
But, the mixture between phenol and iron (III) chloride solution changed from yellow to
violet colour which proved that there is a reaction occurred. Reaction between phenol and iron
(III) solution will produce another organic compound together with hydrochloric acid. The violet
colour changed indicates the presence of phenol or enol in the mixture. The equation involved in
this solution is:

v.

Unknown

Based on chromic acid test, the result verified that unknown A was either primary alcohol or
secondary alcohol. The yellow color of the solution changed to blue-green solution which
produced by chromium (III) sulfate, Cr 2(SO4)3. Unfortunately, due to the errors in the result of
Lucas and Iodoform test, the identification of primary and secondary alcohol of unknown A
cannot be done.
For unknown B, the result from the chromic acid test confirmed that the sample was a
tertiary alcohol. The color of yellow solution remains unchanged after mixing 2-methyl-propanol
with chromic acid. This indicates that unknown B did not undergo any oxidation process to form
either carboxylic acid or ketone. Plus, there was no formation of chromium (III) sulfate,
Cr2(SO4)3 which produce the blue-green color
SOURCES OF ERROR
First, for iodoform test, all the samples are let to be cool only for a short period of time
before the reaction is being observed. Consequently, we cannot observe any yellow precipitate
that should be formed in 2-methly-2-propanol. Second, for Lucas test, the samples in the water
bath are not keep warm, thus the cloudiness in the 2-butanol cannot be observed as it should be.
PRECAUTION STEPS
In iodoform test, all the samples must let to be cool for a longer period of time before
doing any observation because the formation of yellow precipitate tends to be slow. Next, in
Lucas test, the samples in the water bath must keep warm consistently by closing the cover of the
water bath so that the cloudiness that formed can be seen clearly.
CONCLUSION
In conclusion, by conducting this experiment, we managed to determine the physical
properties the chemical reactivity of different classes of alcohols and phenols. We also manage to
identify what is the group that belong to unknown B. Unfortunately, because of some error that
occurred in the experiment, we failed to identify unknown A.

Physical Properties of Alcohols and Phenol

The physical properties of alcohols and phenols are soluble in water. This is because, the
polarity of hydroxyl group that attach to both alcohols and phenols with its ability to form
hydrogen bonds, enable alcohols and phenols mix with water. Meanwhile in acidity properties,
phenol has more acidity than the alcohols.
Chemical Properties of Alcohols and Phenols
Primary Alcohols
Primary alcohols are an alcohol which contains carbon which carries the -OH group is
only attached to one alkyl group. In Iodoform test, only 1-butanol which is primary alcohol gives
positive result. Primary alcohols react with iodine in aqueous sodium hydroxide to give the
yellow precipitate iodoform. In chromic acid test, primary alcohols oxidized and forming an
aldehyde as intermediate and later forming carboxylic acid. However, when tested with Lucas
reagent and iron (III) chloride, primary alcohols do not have any changes in its solution.

Secondary Alcohols
Secondary alcohols are alcohol that, its carbon with the -OH group attached is joined
directly to two alkyl groups, which may be the same or different. For their chemical behavior,
secondary alcohols undergo reaction with Lucas reagent and an alkyl chloride compound is
formed. When mixed with chromic acid, secondary alcohol reacts to form a ketone compound
with blue-green color of solution. However, secondary alcohols do not react when being tested
with Iodoform and iron (III) chloride. Since unknown B showed similar observations with 2butanol throughout the experiment, thus it is categorized in secondary alcohol group.
Tertiary Alcohols
Tertiary alcohols are alcohol that contain carbon atom holding the -OH group is attached
directly to three alkyl groups, which may be any combination of same or different. Tertiary
alcohols can be identified by using Lucas test. In this test, tertiary alcohols react with Lucas
reagent to form an insoluble alkyl chloride indicated by the immediate formation of cloudiness in
the solution. However, tertiary alcohol do not react Iodoform solution, chromic acid and iron
(III) chloride.

Phenol
Phenols are any compound with a hydroxyl group linked directly to a benzene ring. To
identify phenol, iron (III) chloride test is used. When iron (III) chloride solution is added to
phenol, it gives a violet-colored solution indicating that a reaction had occurred. The violet
colour changed indicates the presence of phenol or enol in the mixture. Meanwhile, phenols give
negative result to Iodoform, Lucas and chromic acid test.

REFERENCES
1. http://chemwiki.ucdavis.edu/Organic_Chemistry/Alcohols
2. http://chemwiki.ucdavis.edu/Organic_Chemistry/Alcohols
3. Bailey P.S & Bailey C.A (2000), Alcohols, Phenols and Ethers, Organic Chemistry,
Frentice-Hall, Inc, Sixth Edition, pp. 251-287.
4. http://chemwiki.ucdavis.edu/Organic_Chemistry/Alcohols
5. Bailey P.S & Bailey C.A (2000), Alcohols, Phenols and Ethers, Organic Chemistry,
Frentice-Hall, Inc, Sixth Edition, pp. 251-287.
6. http://www.chemguide.co.uk/organicprops/phenol/acidity.html
7. http://chemwiki.ucdavis.edu/Organic_Chemistry/Alcohols/Reactivity_of_Alcohols/The_
Triiodometha
8. http://sciencehelp.blog.com/2013/01/28/iodoform-test/
9. http://employees.oneonta.edu/knauerbr/chem226/226expts/226_expt08_pro.pdf

LAB REPORT
GENERAL CHEMISTRY
SPL 1113/SAP 1113
Experiment 3 : Identification of Alcohols and Phenols

Lecturers name: Asst. Prof. Dr. Sahena Ferdosh

Date: 11th October 2015

No

Group members

Matric number

.
1

Noor Amni Binti Mohamed

1511170

Muhammad Azimi Bin Shaharudin

1513485

Mardhiyana Najwa Binti Hamdan

1515122

Muhammad Shamin Shazwan Bin Kamarudin

1517141

KULLIYAH OF SCIENCE
INTERNATIONAL ISLAMIC UNIVERSITY MALAYSIA