FACULTY OF SCIENCE

UNIVERSITI TUNKU ABDUL RAHMAN

BACHELOR OF SCIENCE (HONOURS) – BIOCHEMISTRY

YEAR 1, TRIMESTER 2

UDEC1164 – ORGANIC CHEMISTRY

EXPERIMENT 5 – PROPERTIES OF ALCOHOL

NAME: LIM WEY LOON

STUDENT ID: 2207600

PARTNER NAME: CHAI HUI QUAN, TAN XUE YI

STUDENT ID: 2207457, 2204645

PRACTICAL GROUP: P1

PRACTICAL DATE & TIME: 28 FEBRUARY 2023

9.00AM - 11.30AM

LAB INTRUCTOR: DR. SIM KOOI MOW

Title of Experiment: Experiment 5 – Properties of Alcohol

Objectives:

1. To test the properties of different classes of alcohol.

2. To differentiate between different classes of alcohol.
3. To determine the class of alcohol of unknown A and unknown B

Introduction:

An alcohol is an organic compound with a hydroxyl (-OH) functional group on an

aliphatic carbon atom. Because OH is the functional group of all alcohols, we often represent
alcohols by the general formula ROH, where R is an alkyl group. Therefore, the general
formula of alcohol can be written as C nH2n+1OH. Some of the properties of alcohols depend
on the number of carbon atoms attached to the specific carbon atom that is attached to the OH
group. Alcohols can be grouped into three classes on this basis. (LibreTexts Chemistry, 2022)

Alcohols are classified as primary, secondary or tertiary alcohols. The classification is

done in accordance with the carbon atom of an alkyl group is attached to the hydroxyl group.
Primary alcohols are those alcohols where the carbon atom of the hydroxyl group (-OH) is
attached to only one single alkyl group. Secondary alcohols are those where the carbon atom
of the hydroxyl group is attached to two alkyl groups on either side. The two alkyl groups
present may be either structurally identical or even different. Tertiary alcohols are those
which feature a hydroxyl group attached to the carbon atom which is connected to 3 alkyl
groups. (Byju’s, 2023)

Figure 1: From left to right are primary, secondary and tertiary alcohols respectively

Alcohols are consumed as beverages, antiseptic agent, fuels and preservatives for
specimens in the laboratories. Besides, alcohols are used as an anti-freezing agent with a
mixture of a solution containing ethylene glycol dissolved in water. (Byju’s, 2023)
Chemicals/ Reagents:

Ethanol, Isopropyl alcohol, t-Butyl alcohol, unknown A, unknown B, Lucas reagent, chromic
acid solution and sodium metal.

Glasswares:

Test tubes.

Experimental Procedure:

(A) Solubility of Alcohols

1. In three separate dry test tubes, about 1 mL of each of the following: ethanol,
isopropyl alcohol and t-butyl alcohol was placed.
2. About 2 mL of water was added to each tube, the solutions were mixed and observed.
The results were recorded on the notebook.
3. The above procedures were repeated with the two unknown liquids and observations
were made.
4. The above steps were repeated using butanol and observations were made.

(B) Lucas test

1. To 1 mL portions of ethanol, isopropyl alcohol and t-butyl alcohol in separate dry test
tubes, 6 mL of Lucas reagent was added at room temperature.
2. The tubes were closed with a cork and were shaken and the length of time it took for
the mixture to become cloudy or separate two layers was noted. The results were
recorded.
3. The above procedures were repeated with the two unknown liquids and observations
were made.

(C) Chromic acid test

1. To 2 mL portions of ethanol, isopropyl alcohol and t-butyl alcohol in separate dry test
tubes, 1 mL of chromic acid solution was added.
2. Any changes in colour were observed.
3. The above procedures were repeated with the two unknown liquids and observations
were made.
(D) Reaction with metallic sodium

1. To 2 mL portions of ethanol, isopropyl alcohol and t-butyl alcohol in separate dry test
tubes, a small piece of sodium metal was added and any reaction that occurred was
noted.
2. The gas formed from the reaction was determined.
3. The rate of gas evolution relative to each alcohol was compared.
4. The alcohols were arranged in order of increasing acidity based on results and the
reasons were explained.
5. The above procedures were repeated with the two unknown liquids and observations
were made.

Results:

(A) Solubility of alcohols

Alcohol Observation Deduction

Ethanol Soluble in water Short, unbranched aliphatic
Isopropyl alcohol Soluble in water alcohol and branched alcohol
t-Butyl alcohol Soluble in water is soluble in water while long
Unknown A Soluble in water aliphatic alcohol is insoluble
Unknown B Soluble in water in water.
n-butanol Insoluble in water
Table 1: Solubility of alcohols

(B) Lucas Test

Alcohol Observation Deduction

Ethanol No visible changes Primary alcohol gives
Isopropyl alcohol Takes longer time to turn cloudy negative result, secondary
t-Butyl alcohol Immediately turn cloudy. Two layers alcohol reacts slowly while
are formed tertiary alcohol reacts
Unknown A Takes longer time to turn cloudy immediately with Lucas
Unknown B Immediately turn cloudy. Two layers reagent.
are formed
Table 2: Reactivity of alcohol towards Lucas Reagent
 Figure 2: From left to right are the reaction of ethanol, isopropyl alcohol, t-butyl alcohol,
unknown A and unknown B with Lucas reagent

(C) Chromic acid test

Alcohol Observation Deduction

Ethanol Solution turns green Primary alcohol and
Isopropyl alcohol Solution turns green secondary alcohol can be
t-Butyl alcohol Solution remains red-brown oxidised by chromic acid
Unknown A Solution turns green while tertiary alcohol cannot.
Unknown B Solution remains red-brown
Table 3: Reactivity of alcohol towards chromic acid

Figure 3: From left to right are the reaction of ethanol, isopropyl alcohol, t-butyl alcohol,
unknown A and unknown B with chromic acid solution
(D) Reaction with metallic sodium

Alcohol Observation Deduction

Ethanol Vigorous reaction occurs with Primary alcohol reacts
bubbles released readily vigorously, secondary
Isopropyl alcohol Moderate reaction occurs with alcohol reacts moderately
bubbles released slowly while tertiary alcohol reacts
t-Butyl alcohol Slow reaction occurs with bubbles slowly.
released in a small amount
Unknown A Moderate reaction occurs with
bubbles released slowly
Unknown B Slow reaction occurs with bubbles
released in a small amount
Table 4: Reactivity of alcohol towards metallic sodium

Figure 4: From left to right are the reaction of ethanol, isopropyl alcohol, t-butyl alcohol,
unknown A and unknown B with metallic sodium
Discussion:

Each alcohol consists of a carbon chain (always nonpolar) and a OH group (which is
polar). Water is polar and it attracts OH group by forming hydrogen bonds. Carbon chain on
the other hand as nonpolar is repelled. Solubility of alcohols is therefore determined by the
strength of the two forces. Due to the strength of the hydroxyl group, first three alcohols
(methanol, ethanol and propanol) are completely miscible. They dissolve in water in any
amount. Starting with the four-carbon butanol the solubility of alcohols is starting to
decrease. This is because the hydrophobic chain gets longer. (Solubility of Things, 2023)
However, for isopropyl and t-Butyl alcohol (in Figure 1), the carbon chain is relatively short
compared to n-butanol. Hence, the strength of the repelling hydrophobic hydrocarbon chain is
weaker, thus leading to high solubility of isopropyl alcohol and t-Butyl alcohol in water.

The chemical equations for Lucas test are as follows:

ZnCl2
1. Isopropyl alcohol: C3H7OH + HCl C3H7Cl + H2O
ZnCl2
2. t-Butyl alcohol: C4H9OH + HCl C4H9Cl + H2O

Lucas test is based on the difference in reactivity of alcohols with hydrogen halide.
Primary secondary and tertiary alcohols react with hydrogen halide (hydrochloric acid) at
different rates. It follows the SN1 reaction mechanism. The solution of concentrated
hydrochloric acid with zinc chloride is called Lucas reagent. Lucas reagent forms carbocation
as intermediate with all three alcohols. But the stability of carbocation intermediate differs in
all three reactions. Tertiary alcohol gives instant results with Lucas reagent as its carbocation
is highly stable. While secondary alcohol gives results with Lucas reagent after a long time as
its carbocation intermediate is moderately stable and primary alcohol gives negative result
with Lucas reagent at room temperature because its carbocation is highly unstable.

The mechanism of reaction of isopropyl alcohol with Lucas reagent:

 The mechanism of reaction of t-butyl alcohol with Lucas reagent:

(Vedantu, 2023)

The chemical equations for chromic acid test are as follows:

1. Ethanol:
3C2H5OH + 4H2CrO4 + 12H+ 3CH3COOH + 4Cr3+ + 13H2O
2. Isopropyl alcohol:
3(CH3)2CHOH + 2H2CrO4 +6H+ 3(CH3)2C=O + 2Cr3+ + 8H2O

Chromic acid, H2CrO4, is a strong acid and a reagent for oxidizing alcohols to
ketones and carboxylic acids. Primary alcohols can be oxidized to either aldehydes or
carboxylic acids, depending on the reaction conditions. In the case of the formation of
carboxylic acids, the alcohol is first oxidized to an aldehyde, which is then oxidized further to
the acid. Secondary alcohols are oxidized to ketones. Tertiary alcohols cannot be oxidised by
chromic acid without breaking the C-C bonds. The reason is there is no reactive C-H bond at
the carbon atom where the hydroxyl group attaches to.
The mechanism of oxidation of ethanol by chromic acid:

The mechanism of oxidation of isopropyl alcohol by chromic acid:

(ChemiLibre Texts, 2023)

 The chemical equation for reaction with metallic sodium are as follows:

1. Ethanol: 2C2H5OH + 2Na 2C2H5O-Na+ + H2

2. Isopropyl alcohol: 2C3H7OH + 2Na 2C3H7O-Na+ + H2
3. t-Butyl alcohol: 2C4H9OH + 2Na 2C4H9O-Na+ + H2

An alkoxide is an organic functional group formed when a hydrogen atom is removed

from a hydroxyl group of alcohol when reacted with a metal. It is the conjugate base of
alcohol. (Helmenstine, 2019)

ROH ⇌ RO- + H+

The acidity of alcohols decreases while going from primary to secondary to tertiary.
This decrease in acidity is due to steric hindrance, the alkyl groups inhibit solvation of the
resulting alkoxide ion. In more alkyl substituted alcohols, the electron density at oxygen atom
increases and increase the activation energy for proton removal. (Cliffsnotes, n.d.)

Since unknown A reacts slowly with Lucas reagent, give positive result to oxidation
by chromic acid and reacts moderately with metallic sodium, A is a secondary alcohol. While
B reacts immediately with Lucas reagent, is not oxidised by chromic acid and reacts slowly
with metallic sodium, thus B is a tertiary alcohol.

Precaution Steps:

1. The test tubes used have to be dry.

2. Do not bring alcohol near the flame as it is highly flammable.
3. Avoid touching Lucas reagent with hand as it contains concentrated HCl.
4. Do not discard the contents of any tube with un-reacted sodium down the drain. Add
sufficient ethanol to destroy any unreacted sodium metal.
5. The experiment should be conducted under the fume hood as alcohols are highly
volatile.
Conclusion:

In terms of solubility, ethanol, isopropyl alcohol and t-butyl alcohol are soluble in
water. This is due to the ability of alcohols to form hydrogen bonds with water. Unknown A
and unknown B are also water-soluble.

In the Lucas test, primary alcohol gives negative results, secondary alcohol reacts
slowly with Lucas reagent while tertiary alcohol reacts immediately with Lucas reagent.

In the chromic acid test, primary alcohol and secondary alcohols give positive result
to the oxidation by chromic acid while tertiary alcohol cannot be oxidised by chromic acid.

In the reaction with metallic sodium, primary alcohol reacts vigorously with bubbles
released readily. Secondary alcohol reacts moderately with bubbles released slowly. Tertiary
alcohol reacts slowly with bubbles released in a small amount.

Since unknown A reacts slowly with Lucas reagent, give positive result to oxidation
by chromic acid and reacts moderately with metallic sodium, A is a secondary alcohol. While
B reacts immediately with Lucas reagent, is not oxidised by chromic acid and reacts slowly
with metallic sodium, thus B is a tertiary alcohol.
References:

Byju’s, 2023. Types of Alcohols. [online] Available at <https://byjus.com/chemistry/types-of-

alcohols/> [Accessed 2 March, 2023].

Cliffsnotes, n.d. Reactions of Alcohols. [online] Available at

<https://www.cliffsnotes.com/study-guides/chemistry/organic-chemistry-ii/alcohols-and-
ethers/reactions-of-alcohols> [Accessed 3 March, 2023].

Helmenstine, A.M., 2019. Alkoxide Definition in Chemistry. [online] Available at

<https://www.thoughtco.com/definition-of-alkoxide-604706> [Accessed 3 March, 2023].

LibreTexts Chemistry, 2022. Alcohols – Nomenclature and Classification. [online] Available

at
<https://chem.libretexts.org/Bookshelves/Introductory_Chemistry/Basics_of_General_Organi
c_and_Biological_Chemistry_(Ball_et_al.)/14%3A_Organic_Compounds_of_Oxygen/
14.02%3A_Alcohols_-_Nomenclature_and_Classification> [Accessed 28 February, 2023].

LibreTexts Chemistry, 2023. Oxidation by Chromic Acid. [online] Available at

<https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Orga
nic_Chemistry)/Alcohols/Reactivity_of_Alcohols/The_Oxidation_of_Alcohols/
Oxidation_by_Chromic_Acid> [Accessed 2 March, 2023].

Solubility of Things, 2023. Solubility of Alcohols. [online] Available at

<https://www.solubilityofthings.com/water/alcohols> [Accessed 1 March, 2023].

Vedantu, 2023. Lucas test. [online] Available at <https://www.vedantu.com/chemistry/lucas-

test> [Accessed 1 March, 2023].