ENV124

ORGANIC CHEMISTRY FOR ENVIRONMENTAL HEALTH

EXPERIMENT 2
REACTIONS OF ALCOHOLS

STUDENT NAME: ASYRANI ZULAIKHA BINTI MOHD ZUKI

STUDENT ID: 2020472802
PROGRAMME CODE: HS113
COURSE GROUP: P2HS1132A1
INSTRUCTOR NAME: DR. AZRINAWATI MOHD ZIN
START DATE OF ASSIGNMENT: 30 JUNE 2021
DATE OF SUBMISSION: 7 JULY 2021
OBJECTIVE

To carry out a series of chemical reactions to distinguish between primary, secondary and

tertiary alcohols.

CHEMICAL REAGENTS AND APPARATUS

Potassium permanganate( KMNO4) , sodium hydroxide( NaOH), lucas separator, butyl (primary)
alcohol, secondary alcohol, tertiary alcohol, test tubes, test tubes holder , droppers.

INTRODUCTION

Alcohols are organic molecules that contain a functional group called the hydroxyl (-OH)
group. The -OH group of alkyl alcohols can be positioned on different carbon atoms of the
carbon chain. The alcohols are classified as primary, secondary, or tertiary, depending on
whether the hydroxyl group is attached to a carbon that is bound to one, two or three other
carbon atoms. The presence of an alcohol can be determined with test reagents that react
with the -OH group. Different classes of alcohols react differently with sodium metal, oxidising
agents (e.g. potassium dichromate or potassium permanganate) and Lucas reagent.
Therefore, these reagents can be used to differentiate among the three classes of alcohols.
PROCEDURES

PART A - REACTION WITH SODIUM METAL

1. 3ml of butyl alcohol,secondary alcohol and tertiary alcohol were added into the three
clean test tubes by using a dropper.

2. A metallic sodium were added into the every each of the test tubes that contain butyl
alcohol, secondary alcohol and the tertiary alcohol.

3. Observations were recorded.

PART B - OXIDATION WITH ALKALINE POTASSIUM PERMANGANATE SOLUTION

4. The first step was repeated by adding 3ml of butyl alcohol,secondary alcohol and tertiary
alcohol into the three clean test tubes.

5. About 3 drops or 1ml of potassium permanganate(KMNO4) and sodium solution (NaOH)

were added into the every each of the test tubes.

6. Observations were recorded.

PART C - LUCAS TEST

7. the first step was repeated by adding 3ml of butyl alcohol, secondary alcohol, and
tertiary alcohol into the three clean test tubes.

8. 1ml of lucas separator was added into each of the test tubes.

9. After 10 minutes, the observations were recorded.

RESULTS

TABLE 1 : EXPERIMENTAL OBSERVATIONS

COMPOUND PRIMARY ALCOHOL SECONDARY TERTIARY

ALCOHOL ALCOHOL

STRUCTURAL
FORMULA

IUPAC NAME 1-butanol 2-butanol 2-methyl-2-propanol

Steady stream of Lesser bubbles No bubbles are

bubbles present present because a observed because
PART A
because of the reactions slow reaction there is no reaction
between sodium metal between sodium between sodium
with 1-butanol metal and 2-butanol metal and 2-methyl-
2-propanol

Purple colour of solution Purple colour of

becomes colourless and solution becomes
PART B No changes occured
formed a brown colourless and
in the purple colour
precipitate formed a brown
of solution.
precipitate

The colourless solution The solution The solution turns

remained the same. No becomes turbid. Less cloudy. Clear layer of
PART C
reaction occured. visible layer of oil is oil is formed.
formed.
DISCUSSION

Alcohol is usually grouped in 3 types of category which is primary alcohol, secondary alcohol
and tertiary alcohol. Each category give different reaction based on different test. First, when
alcohol reacted with sodium metal, it can form a salt and hydrogen gas. The salt formed
usually known as a sodium alkoxides. This reaction is similar with reaction of water and
sodium but the reaction is much slower than the other one reaction. The similarities in the
structure of the water molecules and the alkyl groups in alcohol is the causing of the slower
reaction. Due to it low density of the alcohols, it made the sodium sinks and it makes steady
stream of bubbles present. Next, when the alcohols is oxidized with alkaline potassium
permanganate solution under the controlled conditions, it will oxidizes primary alcohol to the
carboxylix acids very efficiently. Permanganate ion, MNO-4 also will oxidizes both primary and
secondary alcohols in two conditions, either basic or asidic solution. If alcohols are tested with
Lucas reagent, it will converts the alcohol to the alkyl chlorides. In this reaction, tertiary
alcohol will give an intemediate reaction while secondary alcohol usually show evidence of
the reaction in about 5 minutes which is it takes longer time than the tertiary alcohol. However,
th primary alcohols will never show any reaction

QUESTIONS

1. What are primary, secondary and tertiary alcohol?

Primary alcohol is one of the hydroxy group where it is bonded to a primary carbon atom
and also can be considered as a molecule that contain a “-CH2OH” group. Next,
secondary alcohol is a compound in which a hydroxy group also where the -OH is
attached to a saturated carbon atom where the two other carbon atoms attached to it.
Lastly, tertiary alcohol is also a compound that contain a hydroxy group that attached to a
saturated carbon atom which it has another three carbon atoms attached to it.

2. Arrange the following alcohols in increasing order of reactivity towards sodium metal:
primary alcohol, secondary alcohol, tertiary alcohol.

Tertiary alcohol, secondary alcohol, primary alcohol.

3. How do primary,secondary and tertiary alcohol differ in their reaction towards oxidation?

Primary alcohols can be oxidised to create aldehydes and carboxylic acids; secondary
alcohols can be oxidised to give ketones. Tertiary alcohols, in contrast, cannot be
oxidised without destroying the molecule's C–C bonds.
4. How will you distinguish between primary, secondary,tertiary alcohol with the help of Lucas
reagent?

the lucas test can differentiates between primary,secondary and tertiary alcohol by
the observations of the its carbocations. This can be seen because secondary
carbocations are more stable compare to the primary carbocations. It is also fast
forming than a primary carbocations. The tertiary carbocations is known as the most
stable one because the reactions occurs immediately compare to the secondary
alcohol that reaction take place within 3 to 5 minutes.

5. Explain what happen when :

i) 1-pentanol reacts with Na.

When 1- pentanol reacts with Na, a salt and hydrogen gas will be formed. The salt is known
as sodium alkoxide. It has a similar reaction with water and sodium but this reaction react is
much slower because of the similarities in their structure of water and molecule and also in
the alkyl group in alcohols.

ii) 3-pentanol is heated with acidified K2Cr2O7.

3-pentanol is a secondary alcohol. If it was heated with acidified K2Cr207, it is mean that
oxidation reaction occured. 3-pentanol will be oxidized by K2Cr207 to ketones respectively.
There will be some changes in colours due to the reduction reaction that happened in
K2Cr207.

iii) 2,2-dimethyl-1-propanol reacts with Lucas reagent.

When 2,2-dimethyl-1-propanol reacts with Lucas reagent, a carbon which carries the positive
charge will be only attached to one of the other alkyl group and it can udergo rearrangement
and form a tertiary carbocation. By this, it will give a positive test with Lucas reagent.

CONCLUSION

As the conclusions, the purposes of this experiment is to carry out a series of chemical
reactions to distinguish between primary, secondary and tertiary alcohols. From the result, we
can conclude that we can distinguish between primary,secondary and tertiary alcohol by the
reaction happened between the alcohols and the chemical reagent. Besides ,the reaction that
occured in primary alcohol is really fast compare to the secondary and tertiary alcohol. Last
but not least, the objectives of this experiment has been achieved.