FAKULTI SAINS GUNAAN

UNIVERISITI TEKNOLOGI MARA

CAWANGAN SARAWAK

CHM132 – ORGANIC CHEMISTRY

LAB REPORT
NAME STUDENT ID
ALDRYLIN MICHELL ANAK DAVID IMPIE 2021457582
ALVIN KANYAN ANAK JEREMAIAH 2021450558
AN’NUR NAJWA BINTI ABD BAYAN 2021463836
ANGELINA ELISA ANAK MYDIN 2021605962

CLASS GROUP: AS1152A

EXPERIMENT NO. : 1

EXPERIMENT TITLE: REACTIONS OF ALCOHOL AND PHENOLS

LECTURER: Dr NOR WAHIDA AWANG

DATE OF EXPERIMENT PERFORMED: 13 APRIL 2022

DATE OF SUBMISSION: 15 MAY 2022

INTRODUCTION

Alcohol is an organic compound in the hydroxyl functional group (-OH) which is bind to a
carbon atom. The general formula for alcohol is CnH2n+1OH. Organic compounds that contain
a hydroxyl group will bonded directly to a carbon atom of the benzene ring and called as
phenol.

The structure of alcohol and phenol showed as below:

Alcohol Phenol

The following tests and experiments are designed to illustrate some properties and reactions
of alcohols and phenols.

1. Reaction with Alkali

Since, phenol is more acidic than alcohols and it may be converted to their sodium salts
by reaction with aqueous sodium hydroxide. Usually, sodium salts soluble in water.

2. Reaction with Metallic Sodium

Sodium can replace the hydrogen atom of the hydroxyl group in alcohols and phenols.
The alkoxides that result are strong bases that can be used as a basic catalyst in organic
reactions.

3. Tests to Distinguish Between the Three Classes of Alcohols

The amount of carbon atoms bound to the carbon with the -OH group determines whether
an alcohol is categorised as primary, secondary, or tertiary. The -OH group is connected
to a carbon atom with one alkyl group or to a carbon atom with two or three hydrogen
atoms for primary alcohol.

Depending on the class to which they belong, alcohols treated with a given reagent may
react at different rates or produce different types of products. The structure of an unknown
alcohol can be determined using tests that distinguish between the three kinds.

(a) Lucas Test

A solution of zinc chloride in concentrated hydrochloric acid is the reagent for Lucas
Test. Lucas test is used to differentiate between primary, secondary and tertiary
alcohols, which these three types of alcohols are converted to their chlorides.
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 Tertiary alcohols react instantly and giving insoluble alkyl chlorides, which appears as a
cloudy dispersion or as separate layer. Secondary alcohols dissolve to give a clear
solution (provided R does not have too many carbon atoms in the chain), and will form
chlorides (cloudy solution) within five minutes. Primary alcohols are not converted to
chloride for several hours at room temperature with the reagent.

4. Chromic Acid Oxidation

Potassium dichromate is strong oxidising agent. All alcohols except tertiary alcohols are
oxidised rapidly by chromic acid, which are tertiary alcohol are not. Secondary alcohol
will change to green while primary will change to blue green if the oxidation reaction has
occurred. Tertiary alcohol will stay in orange colour and it is mean there no reaction has
occurred.

In this test, an acetone solution (propanone) of the alcohol to be tested is treated with
solution of chromic anhydride (Cr5+) in sulfuric acid. When alcohols are oxidised, the
chromium is reduced to Cr3+, causing the solutions to turn opaque and greenish.

5. Reaction of Phenols

(a) Reaction with Ferric Chloride

Phenols and other compounds that with a hydroxyl group and attached to an unsaturated
carbon atom (enols) will give a colour (pink, green or violet, which are depend on the
structure of the phenol or enol) with the ferric chloride. This is because of the formation of
certain coordination complexes with the iron. Ordinary alcohols do not react. This test may be
used to distinguish most phenols from alcohols.

OBJECTIVE

To learn the reaction of alcohols and phenols.

APPARATUS
 Test tubes
 Test tube holder
 Dropper
 Measuring cylinder
 Beaker
CHEMICALS:
 Ethanol
 n-butyl alcohol
 t-butyl alcohol
 Cyclohexanol
 n-amyl alcohol
 Phenol
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  1-Naphthol
 10% Sodium hydroxide
 1-propanol
 2-propanol
 Sodium metal
 Benzyl alcohol
 Bromine water
 Ferric chloride
 1-butanol
 2-butanol
 pH indicator
 Lucas Reagent
 Chromic acid

PROCEDURE
(A) Reaction with Alkali
1. 0.5mL or 0.2-0.5 g of each of the following alcohols was placed in four separate
test tubes: n-butyl alcohol,cyclohexanol,phenol,and 1-naphthol.
2. Each tube was filled with 5mL of 10% sodium hydroxide.
3. The result was observed and written down.
(B) Reaction with Metallic Sodium
1. 2mL of each of the following alcohols was put into separate dry test
tubes:ethanol,1-propanol,2-propanol,and orcinol.
2. Each test tube was filled with a little bit of sodium metal and the results was
recorded.
3. Few drops of universal indicator was added to the solution and the results of
observation was written down. (Warning:Do not flush any tube with unreacted
sodium down the drain:sodium reacts severely with water.)Rinse the solution
down the drain after adding enough ethanol to eliminate any unreacted salt.)
(C) Tests to Distinguish between the Three Classes of Alcohols
Lucas Test
1. 2mL each of the following alcohols was put in separate dry test tubes: 1-butanol,2-
butanol,cyclohexanol,n-amyl alcohol,benzyl alcohol,and t-butyl alcohol.
2. 2mL of Lucas Reagent was poured into each of the four test tubes and the results
was recorded.
3. The test tube was shook and how long it takes for the liquid to cloud up or
separate into two layers was recorded.
Chromic Acid Oxidation
1. Each of the six test tubes was filled with 1mL of acetone.
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 2. One drop of the following alcohol or a few crystals (10mg) of the solid alcohol to
be tested was added to each test tube and shake until clear. Then, One drop of the
reagent was added after a good shook.
3. The following alcohols were examined: 1-butanol, 2-butanol, t-butyl alcohol, n-
amyl alcohol, benzyl alcohol and cholesterol.
4. Any changes was kept an eye out for and was taken note of them.
(D) Reactions of Phenol
With Ferric Chloride
1. One or two crystals, or one or two drops of the compounds to be tested (phenol
and 2-propanol) was dissolved in 5mL of water in three separate test tubes.
2. One or two drops of 1% ferric chloride solution was added to each tube and the
test tube was shook gently.
3. Each test tube’s results was examined.
DATA & RESULT
TESTS COMPOUNDS OBSERVATION

REACTION n-butyl double layer formed

WITH ALKALI
cyclohexanol double layer with bubble formed

phenol pink turns into colorless

REACTION Ethanol Bubbles formed and sodium metal dissolved.

WITH Colorless solution become dark green
METALIC
SODIUM 1-propanol Bubbles formed and sodium metal dissolved.
Colorless solution become dark green

2-propanol Bubbles formed and sodium metal dissolved.

Colorless solution become dark blue

LUCAS TEST 1-butanol No cloudiness

2-butanol The solution turn cloudy within 5 min

Cyclohexanol The solution turn cloudy within 5 min

n-amyl alcohol No cloudiness

tert-butyl The solution turn cloudy immediately

OXIDATION 1-butanol turning orange chromic acid to blue green

2-butanol turning orange chromic acid to blue green

t-butyl alcohol turning orange chromic acid to green

n-amyl alcohol turning orange chromic acid to blue green

FERRIC 2-propanol Solution turn to yellow(negative)

CHLORIDE
phenol Solution turn to purple(positive

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QUESTION
1. Which of the following pairs of compounds is more soluble in water?

a) Ethanol and 1-hexanol

Ethanol is more soluble in water than 1-hexanol because it has a hydroxyl
group which containing an O-H bond that are allows it to form hydrogen
bonds mix with the water molecules. While 1-hexanol also has a hydroxyl
group but it has a long molecule or long carbon chain, so its molecules have
high dispersion between them, which making it harder to separate them.

b) 1-propanol and 1,2,3-propanetriol

1,2,3-propanetriol is more soluble in water because it has more than one
hydroxyl group attached on the carbon chain. The existence of a hydroxyl group
in alcohol allows hydrogen bonding between them and almost the same as water.
This led them to form more hydrogen bonds with water molecule.

2. Suggest a chemical test to distinguish the following pairs of compounds. Discuss the
result obtained and write the equation for the reaction.

a) 1-butanol and 2-butanol

These two compounds can be distinguished by using Lucas test. This test was used
to determine the different rates at which primary, secondary, and tertiary alcohols
are converted to their chlorides. Lucas reagent is basically a solution that are
formed by the combination of hydrochloric acid, HCl and zinc chloride, ZnCl2. In
Lucas test, zinc chloride acts as catalyst. 1-butanol is a primary alcohol and the
reaction occur very slow. While 2-butanol is a secondary alcohol. It produces
cloudy after 5 minutes when it starts to react with Lucas reagent.

b) Phenol and phenyl ethanol

These two compounds can be distinguished by using ferric chloride test. The test
was used to determine the presence of phenol. Since phenol is more acidic than
alcohol, so it will react with the ferric chloride solution and turn out a violet color
while phenyl ethanol does not have any reaction to the test. Alcohol is less acidic
compared to phenol eventhough alcohol produce alkoxide,

3. What is Lucas Reagent made of?

Lucas reagent is a solution of anhydrous zinc chloride in concentrated hydrochloric

acid, HCl. Alcohols are soluble in Lucas reagent when they are less than six carbons.

DISCUSSION
a) Solubility
𝑒𝑡ℎ𝑎𝑛𝑜𝑙 ∶ CH3CH2(OH) + H2O → H3O + C2H5O
𝑡 − 𝑏𝑢𝑡𝑦𝑙 𝑎𝑙𝑐𝑜ℎ𝑜𝑙 ∶ (CH3)3C(OH) + H2O → H3O + (CH3)3CO
𝑐𝑦𝑐𝑙𝑜ℎ𝑒𝑥𝑎𝑛𝑜𝑙 ∶ (CH3)3C(OH) + H2O → H3O + (CH3)3CO

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For this experiment, polar molecules are soluble in polar solvents while for polar solvents
molecules are soluble in non-polar solvents. Hydrocarbons which its compound containing
carbon and hydrogen are insoluble in water and are non-polar. The simple alcohols or short-
chain alcohols are completely water soluble in all proportions. Nevertheless, solubility
decreases as the number of carbon atom increases. The solubility for four carbons or more
drastically decreasing and two layers are formed.
From the ethanol’s equation above, we can see that water is added and mixed with ethanol.
The result is soluble. This means ethanol is completely soluble in water. The main
intermolecular attraction is hydrogen bonds. Since ethanol only have two carbons, so it is
completely water soluble.
For n-butyl alcohol, the observation recorded is the alcohol aqueous turned cloudy and white
precipitate are formed when it mixed with water. The reaction that n-butyl alcohol is
insoluble. The reaction might have an error, and this happened because n-butyl alcohol has
four carbons. N-butyl alcohol should be soluble in water.
From the reaction of t-butyl alcohol, it is recorded as soluble in water. The observation is
there is no reaction. There are three carbons from t-butyl alcohol which is still as small
alcohols. So, the solubility in water is increasing.
For cyclohexanol, the observation taken shows the solution turned into cloudy and white
precipitated are formed. This showed that the reaction is insoluble. It happened because
solubility declines as the number carbon increases.
While Iso-amyl alcohol shows the observation of cloudiness.
For phenol, the observation recorded it turn out to be cloudy and white precipitate are formed.
Hence, the phenol is not soluble in water as expectation
b) Reaction with alkali
From these equations:
𝑛 − 𝑏𝑢𝑡𝑦𝑙 𝑎𝑙𝑐𝑜ℎ𝑜𝑙 ∶ C4H9OH + NaOH → C4H9O- Na+ + H2O
𝑐𝑦𝑐𝑙𝑜ℎ𝑒𝑥𝑎𝑛𝑜𝑙 ∶ C6H11OH + NaOH → C6H11O- Na+ + H2O
𝑝ℎ𝑒𝑛𝑜𝑙 ∶ C6H5OH + NaOH → C6H5O- Na+ + H2O
For reaction alcohols and phenol with alkali, alcohols which are n-butyl alcohol and
cyclohexanol resulting a thin layer formed on top of the water (insoluble) meanwhile phenol
become soluble. This shows that the uses of sodium hydroxide in this experiment as alkali
can determine the properties between alcohols and phenols. Both of it are acidic in nature
with the purpose that can donate a proton to a strong base, but this reaction shows the water is
a better proton donator than alcohol resulting the alcohols become insoluble. Meantime
phenols can react naturally and become soluble with aqueous sodium hydroxide forming
sodium phenoxides. Alcohols becoming weaker when in the water in presence of sodium
hydroxide because it is a stronger base. Due to the presence of unshared electron pairs on top
of oxygen, which makes alcohols becoming a proton acceptor.
c) Reaction with metallic sodium

Sodium ethoxide is known as an alkoxide. The way we can determine it as an alkoxide is

when a small piece of sodium metal is placed into ethanol and it reacts gradually to release
hydrogen gas and produces a colourless solution of solution ethoxide, CH3CH2Ona. But for
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this experiment, we are using indicator to distinguish whether the experiment is positive or
negative results. For ethanol and 1-propanol, sodium metal dissolved fast. The hydrogen gas
released and turned the colourless solution into purple colour. This shown that ethanol and 1-
propanol are strong alkali or strong base, thus the test is positive. This can be proved
consorting to the pH indicator which is purple solution (alkali) is around 12-14 in the scale of
pH indicator. Besides, we can see that primary alcohol can react fast with metal sodium.

CH3CH2OH + Na → CH3CH2ONa + H2

Instead, 2-propnaol shows its result has no reaction which is the colourless solution does not
change its colour and the solubility of metal sodium is too slow and there is a little green
colour appear when the bubbles of hydrogen gas released. In conclusion, 2-propanol solution
is neutral and give the negative result for this experiment. This also prove that secondary
alcohol does not react with metal sodium.
d) Test to distinguish between the three classes of alcohols:

i. The Lucas Test

In this experiment, the following alcohols and phenols that are used to test
with Lucas reagent are 1-butanol, 2-butanol, cyclohexanol, n-amyl alcohol,
tert-butyl alcohol. The result for tert-butyl showed its solution turned into
cloudy immediately. This result showed that tert-butyl is water soluble
tertiary alcohol because it immediately formed an alkyl chloride which it is
insoluble in the aqueous solution. The result for 2-butanol and
cyclohexanol both showed the same result which their solutions turned into
cloudy within five minutes. This result shows that 2-butanol and
cyclohexanol are water soluble secondary alcohols because it within five
minutes formed an alkyl chloride. While for 1-butanol and n-amyl butyl,
both showed the same result which there are no cloudiness occur on the
reaction. This showed that both alcohols are in a group of primary
alcohols. The formation of a second liquid phase in the test tube almost as
soon as the alcohol initially soluble in indicative of a tertiary alcohol.

ii. Chromic acid oxidation test

In this experiment, 1-butanol is primary alcohol. 1-butanol are oxidized to

carboxylic acids while the Cr+6 ion in the chromic acid is reduced to Cr+3.
1-butanol colour is turning orange chromic acid to blue green colour.
Nest, 2-butanol is secondary alcohol. So, as expectation the oxidation of
hydroxyl group should forms the ketone carbonyl group. Then, 2-butanol is
oxidized to butanone. The reaction shows that the colour of the solution
turning orang chromic acid to blue green same as 1-butanol.
While for t-butyl alcohol, it is a tertiary alcohol that resist the common
oxidizing agents used to test for alcohol. However, it will dehydrate in the
acidic solution to isobutylene and be oxidized to acetone and carbon
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 dioxide to form aldehyde and carboxylic acid. For n-amyl alcohol, it is a
primary alcohol. So, it can be oxidized to form aldehyde and carboxylic
acid. The colour orange chromic acid are turning to blue green.

e) Reaction with phenols

i) With ferric chloride:
From these equations:
2-propanol: C3H8OH + FeCl3 → Fe(OC3H8)]3- + 3H + 3HCl
2-propanol is secondary alcohol. There is no reaction between 2-propanol and
ferric chloride because 2-propanol isn't acidic enough to react with it. The solution
turns to yellow colour which it is bring out a negative result for this experiment.
phenol: 6𝐶6𝐻5𝑂𝐻 + 𝐹𝑒𝐶𝑙3 → [𝐹𝑒(𝑂𝐶6𝐻5)6]3− + 3𝐻+ + 3𝐻𝐶𝑙
For this reaction, phenol reacts with aqueous neutral ferric chloride to form ferric
phenoxide complex, which is purple coloured. The experiment shows a positive
result. The phenoxides ions form coordinates bonds to the Fe3+ ion while the
hydrogen from the phenol stays in ionic form with chloride ion. On this basis,
aliphatic and aromatic alcohol are distinguished.
CONCLUSION

Several tests were employed in this experiment to investigate the interactions of the hydroxyl
group and the functional group found in alcohols. Alcohols were classified into one of three
categories: primary, secondary, or tertiary, and aliphatic or aromatic, depending on the tests
conducted.

The first test was a solubility test in which water was used as the solvent. Ethanol, n-butyl
alcohol, t-butyl alcohol, cyclohexanol, isoamyl alcohol, and phenol were the alcohol
compounds. Only ethanol and t-butyl alcohols were found to be soluble.

Esters are generated when alcohol reacts with sodium hydroxide in an alkali test. The creation
of a layer in the solution indicates this. The hydroxyl group is either primary or secondary
because the test substance reacted.

In the sodium metal test, ethanol and 1-propanol were the first to react, followed by 2-
propanol, which showed no reaction. Due to steric effects, the rate of the reaction is affected
by the branches of the carbon that contain hydroxyl groups.

2-butanol and cyclohexanol react in the Lucas test within 5 minutes, indicating that they are
secondary alcohols. Because benzyl alcohol and t-butyl show an immediate reaction, they are
tertiary alcohols, but n-amyl alcohol, which has some errors, should be primary alcohol.

2-butanol, benzyl alcohol, and cholesterol reacted in an oxidation test, while tbutyl alcohol
and n- amyl alcohol remained unaffected. Only primary and secondary alcohols are reactive
in this test, it can be said.

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Phenol transforms bromine water from yellow to colourless in a bromine water test. This
indicates that in these reactions, the aromatic ring is activated.

Finally, phenol can react with FeCl3 in a ferric chloride test, although 2- propanol did not.
This is a great way to tell the difference between phenols and alcohol.

To improve the results, start with an oxidation test to define the alcohol classes, then move on
to an alkali test to distinguish between primary and secondary alcohol. After that, utilise it to
validate the tertiary alcohol using the Lucas test. Finally, employ the ferric chloride test to
distinguish between alcohol and phenol with new sets of alcohol compounds.
REFERENCES
https://www.academia.edu/44641599/CHM_301_LAB_REPORT_EXPERIMENT_1_REAC
TION_OF_ALCOHOLS_AND_PHENOL
http://dept.harpercollege.edu/chemistry/chm/100/dgodambe/thedisk/qual/chromic.htm
https://chemistry.stackexchange.com/questions/82609/what-is-the-product-when-ferric-
chloride-reacts-with-propan-1-ol
https://youtu.be/3QIqcdup_Og
https://youtu.be/D6lJZeCxkuM
https://youtu.be/699PmfYQFq8
https://youtu.be/jnedYgJAa70
https://youtu.be/8z8m_XFDKV8
https://youtu.be/tL15my1k-v8

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