CHM301 ORGANIC CHEMISTRY II

REACTION OF ALCOHOLS, CARBONYL AND ESTERS

NAME NURFATHIHA ARFA BINTI AZIS

STUDENT NO. 2019884246

GROUP AS1204_8

LECTURER’S NAME MADAM ROSMAWATI BINTI ABDUL AZIS

INTRODUCTION
These experiments were conducted to demonstrate some of the properties and reactions of
alcohol, phenols, aldehyde, ketone, and synthesis of isopentyl acetate (banana oil).

Alcohol is any of class of organic compounds characterized by one or more hydroxyl

(-OH) groups attached to a carbon atom of an alkyl group (hydrocarbon chain). (Wade, 2021).
While phenol is characterized by a hydroxyl group that attached to a carbon that is part an
aromatic ring. Phenols are comparable to alcohols in structure, but they from stronger
hydrogen bonds, at room temperature, phenols appear as colorless liquids or white solids and
are potentially toxic. The presence of a hydroxyl group in alcohol and phenols allows hydrogen
bonding between them and similar substances such as water. Small alcohols dissolve
completely in water. A single solution is produced by combining the two in any proportion.
However, as the length of the hydrocarbon chain in the alcohol increases, solubility decreases.
The decrease in solubility is noticeable at four carbon atoms and beyond. When the two are
mixed, two-layered substances will emerge in a test tube.

Tollen’s test, also known as silver-mirror test, is a qualitative laboratory test used to
distinguish between an aldehyde and a ketone. It exploits the fact that aldehydes are readily
oxidized, whereas ketones are not. Tollen’s test uses reagent known as Tollens reagent, which
is colorless, basic, aqueous solution containing silver ions coordinated to ammonia [Ag
(NH3)2+]. (Tollens' Test , 2020).

The Fehling test is due to the fact that complexed copper ions oxidize the aldehyde
group of sugar to form acid. The red copper (I) oxide that forms as a result is an indicator of
the redox reaction. In aqueous solution, sugars can exist as a ring or as an open chain
molecule. The positive test will disappear the blue color of Fehling solution and brick-red
precipitate will be seen. For the negative test, the reagent color will remain unchanged.

Some dye formulation reaction, such as the reaction between sodium bisulfite and
fuchsine, produce Schiff reagent. It is often used to test an analyte for the presence of
aldehyde. It can distinguish between aldehydes and ketones. Fuschsine, also known as
rosaniline hydrochloride, is a magenta-colored dye with the chemical formula C20H20N3HCl,
that can be decolored with sodium bisulfate.

KMnO4 is a strong oxidizing agent forming a dark brown colored manganese dioxide
(MnO2) which stains anything organic. It can be readily accepting electrons from the
substances. It reacts violently with sulphuric acid resulting in an explosion. (KMnO4 -
Potassium Permanganate, 2020). KMnO4 test will show positive test to aldehydes, alkenes,
and phenols. Aldehydes will oxidize to carboxylic acids; alkenes will oxidize to glycols.
 Brady’s test is used to detect the presence of aldehydes and ketones. Brady’s reagent
is an aqueous solution of 2,4-dinitrophenyl hydrazine (DNP). It reacts with carbonyl
compounds to give colored precipitates and these precipitates have a sharp melting point that
can confirm the carbonyl compounds.

Esters are carboxylic acid derivatives in which the acyl carbon contains an alkoxy
substituent (OR) rather than the acid’s hydroxyl substituent (OH). Simple esters are widely
used as flavors and fragrances because they have pleasant, fruity scents. Reflux involves
heating the chemical reaction for a specific amount of time, while continually cooling the
vapour produced back into liquid form, using a condenser. The vapours produced above the
reaction continually undergo condensation, returning to the flask as a condensate. (UTSC
Homepage, n.d.)

OBJECTIVES

1. To study the reaction of alcohol and phenol.

2. To study the reactions of aldehyde and ketone.
3. To synthesis ester (Isopropyl acetate) from carboxylic acid and alcohol.

A. REACTION OF ALCOHOL AND PHENOL

A. 1. Solubility

0.5 mL or 0.2-0.5 g of each of the following: ethanol, n-butyl alcohol, t-butyl alcohol,
cyclohexanol, iso-amyl alcohol and phenol were placed in a six separate test tubes. 2
mL of water was added to each test tube and was mixed and observed.

A. 2. Reaction with metallic sodium

2 mL of ethanol, 1-propanol, 2-propanol, and orcinol were placed in a separate dry test
tube. A small piece of sodium metal was added into each test tube and the result was
recorded. Few drops of universal indicator were added to the solution and the result
was recorded.
A. 3. Tests for the three classes of alcohols

The Lucas Test

2 mL of Lucas reagent was placed in each of six test tubes. About five drops of alcohol
were added to be tested. The test tubes then were shaken and the length of time it
takes for the mixture to become cloudy or separate into two layers was recorded. 1-
butanol, 2-butanol, cyclohexanol, n-amyl alcohol, benzyl alcohol and t-butyl alcohol
were tested, and the results were recorded.

Chromic Acid Test

1mL off acetone was placed in each of five separate test tubes. To each test tubes,
one drop of a liquid alcohol or a few crystals (10mg) of a solid alcohol was added to
be tested and was shook until the solution clear. One drop of the reagent was added
then with shaking. These following alcohols were tested: 1-butanol, 2-butanol, t-butyl
alcohol, and benzyl alcohol.

A. 4. Reaction of phenols

With Bromine water

About 0.1g of phenol was dissolved in 3mL of water and bromine water was added
with shaking, until the yellow color persists. The results were observed.

With Ferric Chloride

One or two crystals, or one or two drops of the compounds to be tested in 5mL of
water, were dissolved in three separate test tubes. One or two drops of 1% ferric
chloride solution was added to each test tube, shaken and the results were observed.
Phenol, resorcinol, and 2-propanol were tested, and the results were recorded.
 DATA SHEET
A. REACTION OF ALCOHOL AND PHENOL
Reaction of alcohol
Test Observation

a. Solubility
- Miscible, form homogenous solution
i. ethanol
- Immiscible, insoluble
ii. n-butyl alcohol
- Miscible, form homogenous solution
iii. t-butyl alcohol
- Immiscible, insoluble
iv. cyclohexanol
- Immiscible, insoluble
v. iso-amyl alcohol
- Miscible, form homogenous solution
vi. phenol

b. Reaction with metallic sodium

i. ethanol - A presence of gas bubble

ii. 1-propanol - A presence of gas bubble
iii. 2-propanol - No reaction
iv. Orcinol - No reaction

c. Lucas’s test

i. 1-butanol - solution turns cloudy

ii. 2-butanol - solution turns cloudy
iii. Cyclohexanol - solution turns cloudy
iv. n-amyl alcohol - solution turns cloudy
v. benzyl alcohol - solution turns cloudy
vi. t-butyl alcohol - solution turns cloudy

d. Oxidation

i. 1-butanol - Form precipitate

ii. 2-butanol - Form precipitate
iii. t-butyl alcohol - Form precipitate
iv. n-amyl alcohol - No reaction
v. benzyl alcohol - Form precipitate
Reaction of phenol

Test Observation

a. Bromine water Bromine water decolorized from yellow

color to colorless

b. Ferric chloride
- Colorless solution turns into dark
i. phenol purple
- Colorless solution turns into dark
ii. resorcinol purple
- Colorless solution remains
iii. 2-propanol unchanged

QUESTIONS

1. Select one compound from the following pairs of compounds which is more water
soluble. Explain you answer.

a) Ethanol and 1-hexanol

Ethanol is soluble in water. This is because it has a hydroxyl group that

containing an O-H bond which allows ethanol to form hydrogen bonds with
the water molecules. Hexanol also contain hydroxyl group. However, hexanol
is a long molecule which made it have high dispersion between the
molecules, so it is harder to separate them.

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

1,2,3-propanetriol is more water soluble than 1-propanol. This is because it

has more one hydroxyl group that attached on the carbon chain. The
presence of hydroxyl group in alcohol allows hydrogen bonding between them
and something similar like water. This will allow them to form more hydrogen
bonds with water.
2. Suggest a chemical test(s) to distinguish the following pairs of compounds. Include
the reagent, reaction conditions and observations. Write the equation involved.

a) 1-butanol and 2-butanol

1-butanol and 2-butanol can be distinguished by using Lucas Test. This test
allows us to differentiate the rates of which primary, secondary, and tertiary
alcohols are converted to their chlorides. Lucas’s reagent is a solution formed
by the combination of HCl and ZnCl2 where Zink chloride acts as a catalyst. 1-
butanol consider as a primary alcohol as it reacts very slow with Lucas’s
reagent, 2-butanol is a secondary alcohol as it takes several minutes to
become cloudy after Lucas’s reagent was added.

CH3CH2CH2CH2OH + HCl → CH3CH2CH2CH2Cl + H2O

b) Phenol and phenyl ethanol

These two compounds can be tested with ferric chloride to determine the
presence of phenol. As phenol is more acidic than alcohol, it will react with
the ferric chloride solution and then produce a violet color to indicate the
presence of phenol. Phenyl ethanol does not give any reaction to the test.

FeCl3 + 6C6H5OH → H3(Fe(C6H5O)6) + 3HCl

3. What is Lucas’s reagent made of?

Lucas’s reagents are made of a mixture of concentrated hydrochloric acid and zinc
chloride. The reactivity of the alcohol with Lucas Reagent is measured by the degree
of turbidity which may vary from colorless to turbid. The formation of turbid solution
happens due to the formation of chloroalkane. (Lucas Reagent Formula, Test,
Preparation, Mechanism, MSDS, 2020)
DISCUSSION

A. Solubility
Chemical equations:
Ethanol: CH3CH2(OH) + H2O → H3O + C2H5O
n-butyl alcohol: C4H9OH + H2O → H3O + C4H9O
t-butyl alcohol: (CH3)3C(OH) + H2O → H3O + (CH3)3CO
Cyclohexanol: (CH3)3C(OH) + H2O → H3O + (CH3)3CO
Iso-amyl alcohol: C5H12O + H2O → H3O + C5H11O
Phenol: C6H5OH + H2O → H3O + C6H4O

Polar molecules are soluble in polar solvents and non-polar solvents in this experiment. Since
hydrocarbons (carbon-hydrogen compounds) are non-polar, they are insoluble in water. In all
proportion, small alcohols are completely water soluble. Furthermore, as the number of carbon
atoms increases, solubility decreases. For four carbons or more, which form two layers, there
is a dramatic decrease in solubility.
From ethanol’s equation above, it shows that water is added and mixed with the
ethanol. The results shows that ethanol is fully soluble in water. The main attraction in either
ethanol or water is hydrogen bonds. Ethanol considers as a small alcohol as it only has two
carbons, so it is totally water soluble. The observation recorded that n-butyl alcohol was
immiscible which indicate that n-butyl alcohol is insoluble in water. However, n-butyl alcohol
has four carbons so it should slightly soluble in water. There might be an error occurred which
is precision of measurement. For t-butyl alcohol, the observation recorded that it is miscible
which mean it is soluble in water. It shows no reaction, and it does not appear as two layers
as n-butyl. T-butyl alcohol has three carbons which is a small alcohol, so it increases the
solubility in water. From cyclohexanol’s equation above, the observation recorded shows that
cyclohexanol is immiscible which indicates that it is insoluble in water. This happened because
solubility decreases as the number of carbon increases. For iso-amyl alcohol, the observation
recorded that it is immiscible which indicate that cyclohexanol is insoluble with water.
However, the expectation of cyclohexanol is it should slightly soluble in water, so there must
be some error in this observation. From phenol’s observation, it shows that phenol is
immiscible with water which mean it is insoluble as expected.
B. REACTION OF ALDEHYDE AND KETONE.

B.1. Reaction of methanal

i. 5mL of Tollen’s reagent was poured into test tube and 2mL methanal was
added. The solution was then shake and placed in a bath of warm water.
ii. 5mL of KMnO4 was poured into a test tube then few drops of dilute sulfuric
acid were added. Then 2mL of methanal was added.

B. 2. Reaction of ethanal
i. 1mL of Schiff reagent was poured into a test tube, then few drops of ethanal
was added.
ii. 5mL of Tollen’s reagent was poured into a test tube, then 5mL of ethanal was
added. The solution was shaken and warmed in a bath of warm water.
iii. A mixture of 3mL of Fehling A solution and Fehling B solution was poured into
a test tube. Then, few drops of ethanal was added and mixture was being
warmed in a boiling water bath.
iv. 5mL of KMnO4 was poured into a test tube and few drops of dilute sulfuric
acid was added. Then, few drops of ethanal was added.
v. 3 or 5 drops of ethanal was placed in a test tube, 3mL of 2,4-dinitrophenyl
hydrazine was added. The mixture was heated slowly and carefully with the
Bunsen burner and then let it cool.

B.3. Reaction of propanone

i. 5mL of Tollen’s reagent was poured into a test tube, then 5mL of propanone
was added. The solution was shaken and warmed in a bath of warm water.
ii. A mixture of 3mL of Fehling A solution and Fehling B solution was poured into
a test tube. Then, few drops of propanone was added and mixture was being
warmed in a boiling water bath.
iii. 5mL of KMnO4 was poured into a test tube and few drops of dilute sulfuric
acid was added. Then, few drops of acetone was added and the solution was
leaved for few minutes.
iv. 3 or 5 drops of propanone was placed in a test tube, 3mL of 2,4-dinitrophenyl
hydrazine was added. The mixture was heated slowly and carefully with the
Bunsen burner and then let it cool.
 DATA SHEET
A. REACTION OF ALDEHYDE AND KETONE

Test Observation
Methanal Ethanal Propanone

Tollen’s test Form a silver Form a silver mirror No reaction

mirror color color

Fehling’s test Formed a brick- No change No change

red precipitate

Schiff reagent Reagent color Reagent color Reagent colour

change into dark change into dark change into pink
purple color purple color colour

Reaction with KMnO4 Reagent color Reagent color No reaction

change into dark change into dark
brown color brown quickly
Condensation with Clear yellow turns Clear yellow turns Clear yellow
2,4-DNPH into cloudy yellow into cloudy yellow turns into cloudy
yellow
QUESTION

What is your observation if you differentiate 2-butanone and 2-methylbutanal using Tollen’s
reagent? Write equation involved.

• 2-butanone will turn into aldehyde while 2-methylbtanal turn into ketone. The
hydrogen atom that attaches to aldehydes differ from the hydrogen atom that
attaches to ketones since ketones have no hydrogen atom.
• Since ketone does not react with Tollen’s reagent, there is no reaction when 2-
butanone is mixed with it.
2-butanone

• 2-methylbutanal undergo oxidation when react with KMnO4.

2-methybutanal

DISCUSSION

• Reaction when aldehyde reacts with Fehling’s test

𝑅−𝐶𝐻𝑂+2𝐶𝑢2++5𝑂𝐻−→𝑅−𝐶𝑂𝑂+𝐶𝑢2𝑂+3𝐻2𝑂
C. SYNTHESIS OF ISOPENTYL ACETATE (BANANA OIL).

i. 15mL (12.2g, 0.138mol) of isopentyl alcohol was placed in a 100mL round bottom flask
and 20mL of glacial acetic acid was added.
ii. The flask was switched and 4mL of concentrated H2SO4 was added.
iii. A reflux condenser was attached, and the mixture were reflux using a heating mantel
for 1 hour. The mixture then was let cool in room temperature.
iv. The reaction mixture was placed in separatory funnel and 55mL of cold water was
added. The lower aqueous layer was separated.
v. The organic layer was extracted with 25mL of 5% sodium bicarbonate solution twice
vi. The organic layer was extracted with 25mL water. Finally, 5mL of saturated aqueous
sodium chloride was added to aid im layer separation. The lower aqueous layer was
drew off. The top organic layer was poured into conical and dried with 2g of anhydrous
magnesium sulphate.
vii. The ester was decanted into distilling flask. The distillation apparatus was set up as
described in lab manual. All distilled material were collected but the fraction between
134°C and 143°C were separated in different tared flask. The receiver flask was kept
cold to reduce the vapor escaping into the lab environment. The product weight was
recorded, and the percent yield was calculated.
 DATASHEET
C. SYNTHESIS OF ISOPENTYL ACETATE (BANANA OIL)

1. Mass of product: 16.40g

2. Calculate percentage yield of product:

a) Determination of limiting reagent

1 𝑚𝑜𝑙𝑒 𝑖𝑠𝑜𝑝𝑒𝑛𝑡𝑦𝑙 𝑎𝑙𝑐𝑜ℎ𝑜𝑙

1.675 𝑔 𝑖𝑠𝑜𝑝𝑒𝑛𝑡𝑦𝑙 𝑎𝑙𝑐𝑜ℎ𝑜𝑙) ( 88.2 𝑔 𝑖𝑠𝑜𝑝𝑒𝑛𝑡𝑦𝑙 𝑎𝑙𝑐𝑜ℎ𝑜𝑙 ) = 19.99𝑋10−3 𝑚𝑜𝑙𝑒 𝑖𝑠𝑜𝑝𝑒𝑛𝑡𝑦𝑙 𝑎𝑙𝑐𝑜ℎ𝑜𝑙

1.06 𝑔 1 𝑚𝑜𝑙𝑒 𝑎𝑐𝑒𝑡𝑖𝑐 𝑎𝑐𝑖𝑑

(1.5 𝑚𝐿 𝑎𝑐𝑒𝑡𝑖𝑐 𝑎𝑐𝑖𝑑) ( )( ) = 2.646𝑋10−2 𝑚𝑜𝑙𝑒 𝑎𝑐𝑒𝑡𝑖𝑐 𝑎𝑐𝑖𝑑
1 𝑚𝐿 60.1 𝑔

2.646𝑋10−2 𝑚𝑜𝑙𝑒 𝑒𝑥𝑐𝑒𝑠𝑠 𝑎𝑐𝑒𝑡𝑖𝑐 𝑎𝑐𝑖𝑑

(19.99𝑋10−3𝑚𝑜𝑙𝑒 𝑙𝑖𝑚𝑖𝑡𝑖𝑛𝑔 𝑖𝑠𝑜𝑝𝑒𝑛𝑡𝑦𝑙 𝑎𝑙𝑐𝑜ℎ𝑜𝑙)= 1.32 x’s

b) Theoretical yield
𝑒𝑥𝑐𝑒𝑠𝑠 130.2 𝑔 𝑖𝑠𝑜𝑝𝑒𝑛𝑡𝑦𝑙 𝑎𝑐𝑒𝑡𝑎𝑡𝑒
(𝑚𝑜𝑙𝑒𝑠 𝑜𝑓 𝑙𝑖𝑚𝑖𝑡𝑖𝑛𝑔) ( )( ) (𝑀𝑊) = 𝑡ℎ𝑒𝑜𝑟𝑒𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
𝑙𝑖𝑚𝑖𝑡𝑖𝑛𝑔 1 𝑚𝑜𝑙 𝑖𝑠𝑜𝑝𝑒𝑛𝑡𝑦𝑙 𝑎𝑐𝑒𝑡𝑎𝑡𝑒

1 𝑚𝑜𝑙𝑒 𝑖𝑠𝑜𝑝𝑒𝑛𝑡𝑦𝑙 𝑎𝑐𝑒𝑡𝑎𝑡𝑒 130.2 𝑔 𝑖𝑠𝑜𝑝𝑒𝑛𝑡𝑦𝑙 𝑎𝑐𝑒𝑡𝑎𝑡𝑒

(19.99𝑋10−3 𝑚𝑜𝑙𝑒 𝑖𝑠𝑜𝑝𝑒𝑛𝑡𝑦𝑙 𝑎𝑙𝑐𝑜ℎ𝑜𝑙) ( )( ) =
1 𝑚𝑜𝑙𝑒 𝑖𝑠𝑜𝑝𝑒𝑛𝑡𝑦𝑙 𝑎𝑙𝑐𝑜ℎ𝑜𝑙 1 𝑚𝑜𝑙 𝑖𝑠𝑜𝑝𝑒𝑛𝑡𝑦𝑙 𝑎𝑐𝑒𝑡𝑎𝑡𝑒
2.473 𝑔 𝑖𝑠𝑜𝑝𝑒𝑛𝑡𝑦𝑙 𝑎𝑐𝑒𝑡𝑎𝑡𝑒

c) Percent yield

Formula: (amount prepared/amount possible) X 100% = percent yield

(0.700 g /2.473 g isopentyl acetate) × 100% = 28.31% percent yield isopentyl acetate
QUESTION

1. What is the purpose of extracting the organic layer with 5% aqueous sodium
bicarbonate? Remember, you used an excess off glacial acetic acid.

The product retained in the separating funnel still contains some acidic impurities.
The impurities can be removed by shaking it with aqueous solution of sodium
bicarbonate. The reaction of sodium bicarbonate with acids produces carbon dioxide.

2. What is the purpose of extracting with 25mL of water?

The water extracts any impurities from the product that are soluble in water.

DISCUSSION
The findings for this study clearly show that the ester, isopentyl acetate was synthesized
which has the smell of banana. Direct esterification of acetic acid with isopentyl alcohol
produced 0.7g of isopentyl acetate in this experiment. In the reaction, sulfuric acid was used
as catalyst. To allow esterification to occur, an excess of isopentyl acetate was used to shift
the reaction to the right.

CONCLUSION
All the tests are successfully conducted, and all alcohol, phenol, aldehyde, and ketones
reacted positively and negatively based on its properties.
References
KMnO4 - Potassium Permanganate. (2020, May 23). Retrieved from Vedantu:
https://www.vedantu.com/chemistry/potassium-permanganate

Lucas Reagent Formula, Test, Preparation, Mechanism, MSDS. (2020, March 13). Retrieved from
Chemistry Learner: https://www.chemistrylearner.com/lucas-reagent.html

March, J. a. (2020, october 20). Aldehyde. Retrieved from Encyclopedia Britannica:

https://www.britannica.com/science/aldehyde

Tollens' Test . (2020, September 13). Retrieved from Chemistry Libretexts:

https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Orga
nic_Chemistry)/Aldehydes_and_Ketones/Reactivity_of_Aldehydes_and_Ketones/Tollens_Te
st

UTSC Homepage. (n.d.). Retrieved from Chemistry online @ UTSC:

https://www.utsc.utoronto.ca/webapps/chemistryonline/production/reflux.php

Wade, L. (2021, March 14). Alcohol. Retrieved from Encyclopedia Britannica:

https://www.britannica.com/science/alcohol