FACULTY OF APPLIED SCIENCES

University Technology MARA Sabah Branch, Kota Kinabalu Campus

CHM301 – ORGANIC CHEMISTRY II

SUMMARISED WRITTEN REPORT

REPORT TITLE THE REACTIONS OF ALCOHOLS, CARBONYLS

AND AMINES

MEMBERS NAME / STUDENT ID AMIRATUL FAZIRAH BINTI AMIU (2020874606)

UMAR MUSTAKIM BIN MARSAL @ RAMBLI

(2020893594)

GROUP CHM301 4G1/G2

LECTURER DR. JULENAH BINTI AG NUDDIN

DATE OF SUBMISSION 8TH JULY 2022

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Declaration of Academic Honesty:
Academic honesty or academic integrity is a very important virtue that all students should uphold at
all times.
I/We declare that the lab report submitted is not plagiarised and is entirely my/our own work, and that
no part of it has been copied from any work produced by another person (s)/ source(s) or provided by
any other student(s).
I/We understand that issuing a false declaration can result in severe penalties and I/we am/are willing
to be penalized if any form of copying is found valid.
1.0 INTRODUCTION

According to McMurry (2016) in his book, The Organic Chemistry, alcohols and phenols are
the compounds that are considered as the derivatives of water, H2O as one of the hydrogen atoms is
replaced by an alkyl group. Alcohols are compounds that have one or more hydroxyl groups, OH,
attached to an α carbon atom, which is the carbon that is attached to the OH group in the hydrocarbon
chain. This organic group can be classified into three types based on the number of alkyl groups attached
to the α carbon. Primary alcohols only have one alkyl group attached to the α carbon, the secondary
alcohols have two alkyl groups, and the tertiary ones have three attachments of alkyl groups at the α
carbon. (Wade, 2016). Phenols, on the other hand, have a benzene ring replacing one of the hydrogen
atoms in water. Instead of an aliphatic hydrocarbon chain, phenols are aromatic due to the cyclic
structure of the benzene ring.

Diagram 1 The three classes of alcohols Diagram 2: Phenol structure

Aldehydes and ketones are categorized as carbonyl compounds due to the carbon-oxygen double bond
attached to their structures. Even though aldehyde and ketone are quite similar, but the difference
between these two is the placement of the C=O within the structure. (Clark, 2004).

Diagram 3: Aldehyde and Ketone structure

An aldehyde has the carbonyl group attached at the end of its carbon chain while ketone has another
alkyl group attached to the carbon that is also attached to a carbonyl group. (Reusch, n.d.). Because of
the difference between their carbonyl structure, we can expect some similar and different reactions from
both aldehyde and ketone. (Chemistry School, n.d.).

Amines are the derivations of ammonia, NH3. It consists of a nitrogen atom with a lone pair of electrons,
thus making it basic naturally and nucleophilic. (McMurry, 2016). Amines have three classes just like
alcohols. Primary amines are formed when there is only one hydrogen atom in ammonia being replaced
by an alkyl group. A simple example of primary amine formation is when a benzene ring replaced one
of the hydrogen atoms in ammonia, forming phenylamine also known as aniline.

Diagram 4: The structure of phenylamine (aniline)

2.0 AIM & OBJECTIVES

This experiment aims to conduct a few chemical tests to observe the products from the reactions of
alcohols, carbonyls, and primary amine which are based on the reagents that are used in this experiment.

The objectives of this experiment are:

1. To study the reaction of alcohol and phenol.
2. To determine the reaction of aldehyde and ketone.
3. To investigate the reaction of primary amine (phenylamine) with certain reagents.

3.0 METHODOLOGY
3.1 MATERIALS & APPARATUS

The materials that were needed for the experiment of the reaction of alcohols and phenols are
ethanol, n-butyl alcohol, phenol, 2-propanol, 1-butanol, 2-butanol, and resorcinol. A small amount of
water was used to test the solubility of alcohols and phenol. A solid piece of metallic sodium and a
universal indicator were the materials that are needed in the metallic sodium test. Luca’s reagent was
then used in Luca’s test of both primary and secondary alcohols. Bromine water is an essential material
to indicate the reaction of phenol. 1% of ferric chloride was used to distinguish phenol, resorcinol, and
2-propanol in the ferric chloride test.

Methanal, ethanal and propanone are the materials tested during the second experiment of aldehyde and
ketone’s reaction. Chemical materials such as Tollen’s reagent, Schiff reagent, Fehling A and Fehling
B solution, potassium permanganate (KMnO4) with diluted sulfuric acid (H2SO4), and 2,4-dinitrophenyl
hydrazine are used as the reagents to study the reaction of aldehydes and ketones. For the KMnO4 test,
a small amount of dilute sulfuric acid is used

For the amine experiments, phenylamine was the starting material for each experiment. A few other
chemical materials such as benzoyl chloride, phenolphthalein and bromothymol blue indicators,
hydrochloric acid and distilled water, and bromine water to test the reactions of this primary amine.

The number of test tubes needed depends on the number of materials that are used in each chemical
test. The test tube rack was needed to hold upright the test tubes for better observation. For Tollens and
Felling tests, a set of heating apparatus such as a beaker filled with distilled water, Bunsen burner, retort
stand, and wire gauze are needed to warm or boil the test tubes that require heat for the reaction. A
dropper and measuring cylinder were required to deliver a certain amount of the chemicals to be tested
into the test tubes. To experiment with phenylamine with benzoyl chloride, a stopper was needed to seal
the test tube and avoid any leak of gas while shaking the solution in the test tube.
3.2 EXPERIMENTAL PROCEDURE

3.2.1 Reactions of alcohols and phenols

Solubility

0.5 mL of each of the following, ethanol, n-butyl alcohol, and phenol placed in three separate test tubes.
2mL of distilled water was added to each test tube which was then mixed and observed. The
observations were recorded in the datasheet.

The reaction with metallic sodium

2mL of each of the following, ethanol, and 2-propanol, was placed in separate dry test tubes. A small
piece of sodium metal was added to each test tube and the result was noted in the datasheet. A few drops
of universal indicator were added into the solution and the result was recorded. An amount of enough
ethanol was added to any unreacted sodium, and then the solution was rinsed down the drain.

Lucas Test

2mL of Lucas reagent was placed in each two test tubes. Five drops of 1-butanol and 2-butanol were
added to each test tube. The alcohols were added to be tested and shaken and the length of time it takes
for the mixture to become cloudy or separate into two layers was recorded. The results were recorded
in the datasheet.

The reaction of phenol with bromine water

3mL of phenol was dissolved in 3mL of distilled water. A few drops of bromine water were added while
shaking the test tube until the yellow colour became persisted. The result was observed and recorded in
the datasheet.

The reaction of phenol with ferric chloride

5mL of distilled water was added to three separate test tubes. Two drops of phenol, resorcinol and 2-
propanol were added into separate test tubes. To each test tube, two drops of 1% ferric chloride solution
were added, shaken and the results were observed. The results were recorded in the datasheet.

3.2.2 Reactions of aldehydes and ketones

Tollen’s Test

5mL of Tollen’s reagent was added into three different test tubes. Methanal was added into the first test
tube, ethanal was added into the second one, and propanone was added into the third test tube. The test
tubes were shaken and placed in a bath of warm water.
Fehling’s test

1.5 mL of Fehling A solution and 1.5 mL of Fehling B solution were added into two test tubes. A few
drops of methanal were added into the first test tube and drops of propanone were added into the second
one. Both test tubes were placed in a boiling water bath.

Schiff reagent

1 mL of Schiff reagent was added into a test tube. A few drops of ethanal then added into the same test
tube.

Reaction with Potassium permanganate (KMnO4)

5 mL of potassium permanganate (KMnO4) solution and a few drops of dilute sulfuric acid (H2SO4)
into three different test tubes. 2 mL of methanal was added into the first test tube, drops of ethanal in
the second one and drops of propanone added into the third test tube.

Condensation with 2,4–dinitrophenyl hydrazine (2,4-DNPH)

3 to 5 drops of ethanal and propanone were added into two different test tubes. 3 mL of 2,4–
dinitrophenyl hydrazine was added into each test tube. The test tube with ethanal was heated slowly on
top of Bunsen burner. The propanone test tube was left for a minute.

3.2.3 Reactions of amines

The reaction of phenylamine with benzoyl chloride.

1 mL of phenylamine was added to a test tube, followed by 5 mL of sodium hydroxide. The test tube
was stoppered and shaken hardly for at least 1 minute. 1 mL of benzoyl chloride was added to the test
tube before it stoppered again and shaken hardly for 2 minutes. The test tube was cooled down and the
observation was recorded.

The reaction between phenylamine with indicators

1 mL of distilled water was added to 2 clean test tubes. 0.5 mL of phenylamine was added to each test
tube. 2 drops of phenolphthalein indicator were added to the first test tube while 2 drops of bromothymol
blue indicator were added to the second test tube.

Solubility of phenylamine
1 mL of phenylamine was added to 2 clean test tubes. 3 mL of dilute HCl was added to the first test
tube and the solubility was observed. In the second test tube, 1 mL of distilled water was added, and
the solubility was observed.
The reaction of phenylamine with Bromine Water

2 mL of water was added to a test tube. 1 mL of phenylamine was added to the test tube. Then, bromine
water was added to the test tube drop by drop. The test tube was then shaken for a while. The observation
was recorded in the datasheet.

4.0 RESULTS

Table 1: The reactions of alcohols and phenols.

Experiment Observation
A. Solubility test
i. ethanol Only a monolayer solution is formed.
ii. n-butyl alcohol Only a monolayer solution is formed.
iii. phenol Two layers which are phenol and water are formed.

B. Reaction with metallic After sodium metal is added to After a universal indicator is added
sodium a test tube
i. ethanol Bubbles formation in the solution. The colour changed into light purple.

ii. 2-propanol Bubbles formation in the solution. The colour changes into dark purple

C. Lucas Test
i. 1-butanol No changes were observed. The solution remains colourless.
ii. 2-butanol No changes were observed. The solution remains colourless.

D. Bromine water test A yellowish cloudy solution with white precipitates is formed.

E. Ferric Chloride test

i. Phenol The colourless solution changed to bluish-purple colour.

ii. Resorcinol A yellowish cloudy solution with precipitate is formed.

iii. 2-propanol The solution remains colourless.

Table 2: The reactions of aldehydes and ketones.

Test Observation
Methanal Ethanal Propanone
Tollen’s test The solution turned The solution turned No colour
into grey colour into silver colour changes

Fehling’s test A yellowish-red No colour

precipitate was changes
formed

Schiff reagent A reddish-purple

solution was formed
Reaction with KMnO4 Two layers were Black precipitate No colour
formed with the was formed changes
bottom had brownish
black precipitate and
the top layer with
brownish solution.
Condensation with Black precipitate Yellow precipitate
2,4-DNPH was formed was formed

Table 3: The reactions of phenylamine.

Experiment Observation
Benzoyl chloride Two layers are formed with the top being the phenylamine layer and
the bottom is filled with white solution.
Reaction with pH Phenolphthalein Bromothymol blue
indicators Two layers are formed with the The blue colour of the indicator
top being a colourless layer and remained in the test tube.
the bottom being the
phenylamine layer.
Solubility Dilute HCl Distilled water
Phenylamine dissolved in dilute Two layers were formed with the
HCl solution and yellowish top layer being the water and the
colour changed into almost bottom being the oily
colourless. phenylamine layer.

Bromine water A white, cloudy solution was formed at the top of phenylamine.
5.0 DISCUSSION

5.1 THE REACTIONS OF ALCOHOLS AND PHENOLS

5.1.1 Solubility

It is observed that both ethanol and n-butyl alcohol are immediately dissolved in distilled water.
The observation is a result of the polarity of the alcohols, thus hydrogen bonding is capable between
both alcohols and water molecules to form a homogenous monolayer solution. These alcohols are likely
to form a bond with water because of the hydroxyl group, O-H, a hydrophilic group that is easily
attracted to water molecules.

CH3CH2OH +H2O → CH3CHO + H2 + H2O

Diagram 5: The reaction between ethanol and water molecules

CH3CH2CH2CH2OH + H2O → CH3CH2CH2CHO + H2 + H2O

Diagram 6: The reaction between n-butyl alcohol and water molecules

Nonetheless, phenol on the other hand gave a different observation from ethanol and n-butyl alcohol.
There are two layers formed: the top layer being water and the bottom layer containing a little amount
of the remaining non-dissolved phenol. It is because phenol is an organic compound which contains a
benzene ring that is bonded to a hydroxyl group, O-H.

Diagram 7: The reaction of phenol in water molecules

The solubility of phenol is influenced by the O-H presence in the compound, and it is involved in the
formation of intermolecular hydrogen bonding with water. Hence, O-H makes phenol soluble in water.
However, since phenol has a cyclic structure, one hydrogen atom is removed from the ring to form an
aryl group. Aryl group is hydrophobic, thus decreasing the solubility of phenol in water.

5.1.2 Reactions with metallic sodium

The reaction between alcohol with alkali metal produces a strong base of sodium alkoxide and
hydrogen gas. Alcohol is less acidic than water molecules but very reactive with highly reactive metals
such as sodium, and Na. In the reaction, the metal will replace the hydrogen atom from the hydroxyl
group, O-H, thus forming a basic salt and hydrogen gas.

2Na + 2ROH → 2RO-Na+ + H2

Diagram 8: The reaction between alcohol and metallic sodium

When sodium metal was dropped into the test tube which contains the ethanol, it reacts steadily to
produce a white precipitate of sodium ethoxide, CH3CH2O-Na+ and bubbles formation which indicates
the presence of hydrogen gas.
 2Na + 2CH3CH2OH → 2CH3CH2O-Na+ + H2
Diagram 9: The reaction between ethanol and metallic sodium

The mechanism reaction for 2-propanol is the same as ethanol with the major product that formed being
sodium isopropoxide.

2Na + 2CH3CH(OH)CH3 → 2CH3CO-Na+CH3 + H2

Diagram 10: The reaction between 2-propanol and metallic sodium

A universal indicator was used to estimate the pH value of each of them by observing the colour formed
in the solutions. After adding the universal indicator to each test tube, it is observed that sodium ethoxide
changed into light purple while the sodium isopropoxide showed a darker violet colour. Referring to
the scale of universal indicator colours for acidity, the darker the colour, the higher the basicity. In
essence, in terms of basicity, sodium isopropoxide is stronger than sodium ethoxide.

5.1.3 Luca’s test

From the Luca’s Test which was conducted in this experiment, it is observed that there was no
colour change in both 1-butanol and 2-butanol. Hypothetically, the observation is accurate to describe
how1-butanol, which is a primary alcohol, cannot react with Lucas’ reagent at room temperature. The
carbocation formed from primary alcohol is very unstable, thus the reaction cannot occur easily.

𝑍𝑛𝐶𝑙2
CH3CH2CH2CH2-OH + HCl → No Reaction
Diagram 11: The reaction of 1-butanol in Luca’s reagent

However, 2-butanol which is secondary alcohol is supposed to give a turbid solution with an oily layer
within five minutes. The carbocation formed in secondary alcohol is more stable than in primary
alcohol. The reason for this inaccurate result is probably due to an error in preparing the correct volume
of any chemical involved.

𝑍𝑛𝐶𝑙2
CH3CH2CH(OH)CH3 + HCl → No Reaction
Diagram 12: The reaction between 2-butanol in Luca’s reagent

5.1.4 Bromine water test

When bromine is added to phenol in water, some white precipitate was formed which is the
2,4,6-tribromophenol, and the orange colour of bromine water decolourised a little and only left a
slightly yellowish colour.

C6H5OH + 3Br2 → C6H3Br3O (white ppt) + 3HBr

Diagram 13: The reaction between phenol and bromine

In this reaction, the hydrogen atoms in the benzene ring were substituted by the bromine molecules.
When phenol is treated with bromine in a polar water solvent, the reaction involved a polybromide
derivative. The hydrogen atoms which are in ortho, meta, and para locations concerning the hydroxyl
group, O-H, were substituted with bromine atoms.
Aqueous phenol enables the ionization of phenol to form peroxide ions which are negatively charged
ions. The negative charge in the benzene ring allows it to be more active, thus the tri substitution of
the hydrogen atoms occurred to form 2,4,6-tribromophenol.

5.1.5 Ferric chloride test

Ferric Chloride Test is used to detect the phenol in a sample given by observing the colours
produced at the end of the reaction. Compounds with phenol will show a change of colour such as blue,
violet, purple, green or red-brown when aqueous ferric chloride is added. In this experiment, both
phenol and resorcinol changed from colourless to violet and yellow respectively. The change of colours
indicates the presence or absence of phenols. In phenol reaction, the major product, which is ferric
phenoxide, Fe(C6H5O)3 produced a violet colour solution. Hence, phenol shows a positive result in the
ferric chloride test.

C6H5OH + FeCl3 → Fe(C6H5O)3 (Ferric phenoxide complex) + 3HCl

Diagram 14: The reaction between phenol and ferric chloride

However, in the resorcinol reaction, the solution produced a yellow colour solution.

C6H4(OH)2 + FeCl3 → 2Fe(C6H4HO2)3 + 3HCl

Diagram 15: The reaction between resorcinol and ferric chloride

Since resorcinol has the same structure as phenol, it should give the same violet colour or blue solution
at the end of the experiment to show the presence of a benzene ring in its compound.

Diagram 16: Resorcinol and ferric chloride reaction mechanism

5.2 THE REACTIONS OF ALDEHYDES AND KETONES

5.2.1 Tollen’s test

Tollen’s test also known as silver-mirror test is used to distinguish between the aldehydes and the
ketones which the positive results is based on the formation of grey or silver solution due to an oxidation
reaction. Tollen’s reagent is a colourless, basic aqueous solution that contains silver ions coordinated
with ammonia [ Ag(Nh3)2+]. (Chemistry Libretext, 2020.) In this experiment, Tollen’s test was
succeeded to oxidize both methanal and ethanal but failed to form any silver mirror in propanone. It is
because the redox reaction; oxidation of aldehydes into carboxylic acid and the reduction of silver ions
into metallic silver.
 Diagram 17: Example of aldehyde reaction with Tollen’s reagent

Methanal was oxidized into formic acid while ethanal became ethanoic acid. The formation of grey
and silver solution in the test tube indicates the positive result of the test.

CH₂O + 2OH– + 2[Ag(NH3)2]+ → CH2O2 + H2O + 2Ag + 4NH3

Diagram 18: The reaction between methanal and Tollen’s reagent

CH3CHO + 3OH– + 2[Ag(NH3)2]+ → CH3COOH + 2H2O + 2Ag + 4NH3

Diagram 19: The reaction between ethanal and Tollen’s reagent

5.2.2 Fehling’s test

Fehling’s test is a chemical test that is used to distinguish between the water-soluble aldehydes and the
functional group of ketones. Fehling’s solutions consist of two separate solutions which are Fehling’s
A and Fehling’s B. The two solutions were mixed before testing a chemical compound with the same
amount of each other. Fehling’s A solution contains copper (II) sulphate while Fehling’s B is a mixture
of potassium sodium tartrate and sodium hydroxide. (ByJu’s, n.d.). The mixture of both Fehling’s
solutions formed a deep blue solution which is the bistartratocuprate (II) complex.

When ethanal was added to Fehling’s solution and heated to boiling temperature, a yellowish red
precipitate was formed, indicating a positive result from the test. It is because of the presence of
aldehyde in ethanal that was oxidized by the bistartratocuprate (II) complex to become ethanoic acid.
The oxidation then led to the reduction of copper (II) ions to become copper(I), forming a red precipitate
of copper(I) oxide. (Clark, 2004).

RCHO + 2 Cu2+ + 5OH− → RCOO− + Cu2O (red ppt) + 3 H2O

Diagram 20: The formation of copper oxide (red precipitate)

For propanone, there was no change of colour due to the absence of the aldehyde group and α hydroxy
ketone that can ensure the reduction of the copper ions, thus the result is negative.

5.2.3 Schiff reagent

Schiff reagent test is conducted to detect a presence of an aldehyde in a chemical compound and
differentiate aldehydes and ketones. The Schiff reagent is a product of a reaction between sodium
bisulfite and rosaniline hydrochloride, also known as fuchsine. Fuchsine is a chemical dye with a
magenta colour that is decolourized by sodium bisulfite to form a Schiff reagent. The magenta colour
will reappear if there is a detection of aldehyde during the test. (Chemistry Learner, n.d.)
 Diagram 21: Schiff test of ethanal

When ethanal was added to the Schiff reagent, the colourless solution changed into a reddish-purple,
indicating ethanal is an aldehyde.

5.2.4 Reaction with KMnO4

Potassium permanganate (KMnO4) is a strong oxidizing agent and can be used to differentiate an
aldehyde from a ketone by the oxidation reaction. This test involves a redox reaction; the oxidation of
aldehyde to become carboxylic acid and the reduction of manganate (VII) ions. From the test that we
conducted, it is observed that a black precipitate was formed after ethanal was added into the KMnO4
solution. The black precipitate is the product of reduction of manganate (VII) ion, MnO4-, becoming the
solid manganese (IV) oxide, MnO2. The purple colour of KMnO4 became colourless indicates the
oxidation of ethanal was occurred in the test tube, thus giving a positive result. The reaction of ethanal
and KMnO4 can be expressed with the equation:

3CH3CHO (aq) + 2MnO4– (aq) + H2O (l) → 3CH3COOH (aq) + 2MnO (s) + 2OH– (aq)
Diagram 22: The reaction between ethanal and potassium permanganate

However, due to ketone being very resistant to oxidation, there was no reaction occurred, thus there
was no colour changes to the purple colour of KMnO4 solution or any formation of a precipitate.

5.2.5 Condensation with 2,4-DNPH

2,4-dinitrophenylhydrazine, also known as Brady’s reagent, can react with carbonyl compounds such
as aldehydes and ketones to form 2,4-dinitrophenylhydrazone, a yellowish-orange precipitate.

Diagram 23: Aldehyde reaction with 2,4-DNPH

The carbon-oxygen double bond in both aldehyde and ketone gives positive results for both carbonyls.
In this experiment, when the mixture of ethanal and 2,4-DNPH was heated on top of the Bunsen burner,
a mass of black precipitate was formed at the bottom of the test tube. Propanone, on the other hand,
formed a bright yellowish-orange precipitate in the test tube without any heat. Each reaction indicates
the presence of the C=O group in their compound, thus the test is positive for both carbonyl compounds.

5.3 REACTIONS OF PRIMARY AMINE

5.3.1 Benzoyl chloride

Benzoyl chloride is an acyl chloride that consists of a benzene ring with the acyl chloride group
replacing one of the hydrogens attached to the aromatic hydrocarbon chain. When the phenylamine
reacted with benzoyl chloride, the lone pair from the amine group attacked the acidic carbon from the
benzoyl chloride.

Diagram 24: the mechanism of benzoyl chloride with aniline

The amine group was deprotonated and the oxygen in the benzoyl group reformed the π bond with the
carbon atom. The chlorine atom then left the compound alongside the proton, H+ from the deprotonation
of the amino group to form hydrochloric acid which is the by-product of the reaction. N-phenyl
benzamide was produced in form of a white solution as observed in the experiment.

Diagram 25: The white solution of N-phenyl benzamide.

C7H5ClO + C6H5NH2 → C13H11NO + HCl

Diagram 26: The reaction between aniline and benzoyl chloride

5.3.2 Phenolphthalein and bromothymol blue indicators

Phenolphthalein (C20H14O4) is one of the frequently used to indicate the pH value of certain chemicals.
(Helmenstine, 2022). Because of its basic nature, phenylamine is supposed to give a fuchsia solution
after added with phenolphthalein. Due to the polluted test tube, there was no reaction occurred in the
experiment and the phenylamine solution remained colourless.
However, the reaction for bromothymol blue indicator was a success. Phenylamine attained the blue
colour, indicating its pH level to be slightly higher than 7.5.

Diagram 27: Phenylamine in bromothymol blue solution

5.3.3 Solubility
Phenylamine is completely dissolved in diluted hydrochloric acid, HCl. Since phenylamine is a base,
reacting with a strong acid like HCl will initiate the acid-base reaction. (Clark, 2016). The reaction then
formed an ammonium salt with the appearance of a yellowish, cloudy solution in the test tube which is
known as phenyl ammonium chloride.

Diagram 28: Aniline dissolves in hydrochloric acid solution

Diagram 29: The reaction of aniline in hydrochloric acid solution

Phenylamine has a structure of a benzene ring attached to the amine. When phenylamine dissolves in
hydrochloric acid, the lone pair that is attached to amine (NH2) will undergo partial delocalisation into
the benzene ring. It enables amine to undergo protonation by attracting a proton from an acid. A
hydrogen ion, H+ from hydrochloric acid attached to the amine group, forming a positively charged
ammonium cation, NH3+. Phenylammonium chloride is a readily soluble salt, thus phenylamine is
miscible in HCl.

However, the observation of phenylamine in water is different. Phenylamine forms a layer under the
water molecules and remains non-soluble. It is because of the huge hydrophobic benzene ring that is
attached to the amine group inhibiting the formation of hydrogen bonding with water molecules. (Clark,
2016).
 Diagram 30: Aniline does not dissolve in water molecules

5.3.4 Bromine water

Phenylamine can react with an aqueous solution such as aqueous bromine water without any catalyst
and heat. When phenylamine reacted with bromine water, a bromination reaction occurred even at room
temperature. The reaction produced a white precipitate known as 2,4,6-tribromophenylamine in the
solution and the bromine colour decolourized. (ByJu’s, n.d.). Hydrogen bromide gas was formed
alongside the white solid product.

Diagram 31: The formation of 2,4,6-tribromophenylamine, a white precipitate

Diagram 32: The reaction of phenylamine in bromine water

The NH2 group that attached to the benzene ring increased the reactivity of phenylamine just like how
the OH group affects phenol. Other than that, the NH2 group also gave an activating effect to certain
positions, whether it is beside or opposite to the NH2 group in the cyclic structure of phenyl. The effect
caused bromine atoms to attack the second, fourth and sixth carbons, forming 2,4,6-tribromo
phenylamine. (Clark, 2016)
CONCLUSION

From the experiments that we conducted, it can be concluded that the alcohols are more soluble
than phenols. The solubility of alcohol depends on the length of the carbon chain in the compound. The
reaction between alcohol and sodium metal produced a strong base and hydrogen gas. Secondary
alcohols, which can form more stable carbocations ions, are more reactive to Lucas’s reagent better
than primary alcohols. The reaction between phenol and bromine water produced a white precipitate
known as 2,3,4-tribromophenol. Only phenols that have a benzene ring can react with ferric chloride to
produce colourful solutions.

Based on the chemical tests conducted, it is concluded that aldehydes are more reactive than ketones
due to the hydrogen atom attached to the aldehyde that makes it easier to get oxidized and being a better
reducing agent than any ketone. The carbonyl group in aldehyde is more positively charged than in
ketone because it only has one electron donor than ketone which has two electrons donor instead.
Ketones are very resistant to oxidation, thus there is no reaction occurs in Tollen’s, Fehling’s and
KMnO4 tests.

Phenylamine or its common name, aniline, is a primary amine that can dissolve in a strongly acidic
solution such as hydrochloric acid, HCl due to its basicity to properly react with acid, thus forming a
soluble ammonium chloride salt. Because of the presence of a hydrophobic benzene ring, aniline is not
soluble in water molecules.
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