Organic Chemistry Final 1

Organic Chemistry - CH4102
Experiment 3: Preparation of Acetaldehyde
Lab Report:
Experiment 3
Name: Teniola Abioye Date: 16/04/2021

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Title
Preparation of Acetaldehyde
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What are the objectives of this laboratory session?

The main objectives of this experiment is to create an acetaldehyde aqueous solution by oxidizing
ethanol and to characterize the solution by conducting two chemical tests on it.
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The main learning objective was improving abilities in using Quickfit glassware.
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The other learning objective to understand the problems that could arise in order to prevent an
unwanted side reaction, which for this experiment produces acetic acid (ethanoic acid) from the
acetaldehyde (ethanal) due to further oxidation (Singh, n.d.).
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Pre-Laboratory Questions
i. What are your starting reagents?
• Ethanol
• Sulfuric acid
• Sodium Dichromate
ii. Draw a structural formula of your starting reagents.

What is the functional group of your starting reagents? (Draw a circle around
functional group).
H H
| |
H–C–C–O–H
| |
H H Ethanol – Alcohol
O
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H–O–S– O–H
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O Sulfuric acid - two oxo and two hydroxy groups
O O
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-
Na+ O – Cr – O – Cr – O- Na+
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O O Sodium Dichromate
iii. What is the most common method of preparation for aldehydes? What is
purpose of the sodium dichromate in this experiment?
• The most common method of preparing aldehydes is oxidizing primary alcohols.

• Sodium dichromate is used in conjunction with sulfuric acid to prevent further oxidation of
the aldehyde into carboxylic acid as it works as the oxidizing agent (chemguide, 2015).
iv. What is a Silver Mirror Test used for?
This test is used to distinguish between a ketone and an aldehyde. It takes advantage of the fact that
aldehydes are easily oxidized when ketones aren't. This may be important to know since aldehydes
are made from oxidized primary alcohols, while ketones are made from oxidized secondary alcohols
(Anon, 2020) .
v. What is an Iodoform Test used for?
This test also tests for the presence of the aldehyde. If the test is positive, a yellow precipitate of
triiodomethane is produced by an aldehyde or ketone that contains a specific group. Because ‘R’ is
hydrogen, the chemical is ethanal (mcdaniel, n.d.).
vi. Are any of today’s chemicals considered hazardous?

The chemicals that were used for the experiment that were considered hazardous were
• Ethanol
• Sodium Dichromate
• Sulfuric acid
• The produced acetaldehyde solution
• Dilute sodium hydroxide solution
• Dilute ammonia solution
• Aqueous potassium iodide solution
• Hypochlorite solution
From the safety point of view, what do you need to know about:
• Sodium dichromate
o This chemical can affect a person if it passes through the skin or is
inhaled.
o Could cause irritation to nose, throat and lungs and cause wheezing or
coughing.
Long term effects of exposure could be

o It could cause asthma like allergies or skin allergies.
o It may cause damage to liver and kidneys.
o It could cause division hole in septum in the inner nose
o It is a carcinogen, could caude lung cancer.
1. If in contact with eyes, flush eyes adequately with large amounts of water for a duration of at
least 30 minutes.
2. If in contact with skin, immediately remove contaminated clothing, Wash contaminated skin
with a large quantity of water straight away.
3. If inhaled, remove victim from exposure, begin rescue breathing or CPR in extreme
circumstances and transfer to medical facility (New Jersey Department of Health, 2009).
This page has been intentionally left blank for recording any data, notes, deviations or
observations made during your experiment. Ensure it is signed before leaving the lab.
Experimental:
Table 1 : Equipment and chemicals
Equipments Chemicals
Distillation equipment Ethanol
Round bottom flasks Sodium Dichromate
Beakers Sulfuric acid
Test tubes Dilute sodium hydroxide solution
Test tube holders. Dilute ammonia solution
Glass stirring rod Aqueous potassium iodide solution
Retort stand and clamp Hypochlorite solution
pH testers Deionised water
Graduated flask
Weigh scale
Thermometer
Procedure
1. 8.5ml of concentrated sulfuric acid is added slowly to a round bottom flask filled with 25ml
of distilled water.
2. 3 boiling beads were added to the round bottom flask. The flask was then clamped onto retort
stands.
3. 25g of sodium dichromate was dissolved into a beaker of 25ml distilled water. The solution
was mixed with a glass stirring rod till homogeneous and completely dissolved.
4. 25ml of ethanol was then slowly added into the dichromate and swirled till homogeneous.
5. The distillation equipment was set up.
6. The ethanol dichromate was poured into a dropping funnel with a closed tap with the help of
a pouring funnel.
7. The dropping funnel was then placed into the neck of the Claisen head. The heat was turned
on and the solution was brought to a boil.
8. When the solution was boiling the heat was turned off and the heating mantle was lowered
9. The tap was opened so that the solution would fall in droplets so that all would be gone in 5-7
minutes.
10. The temperature in which the solution was being distilled at was taken at the start and finish.
Test 1
1. A pH dip stick was dipped into the acetaldehyde and was checked for pH on the box.
Test 2
1. 5ml of silver nitrate was added into a test tube. 2-3 drops of 1M NaOH was added to the test
tube. A brown precipitate formed.
2. Dilute ammonia solution was added drop by drop till the brown precipitate nearly
disappeared.
3. A few drops of acetaldehyde was added to the test tube and stirred then was left to settle.
4. The test tube was placed in a warm water bath to quicken the reaction.
5. The test was confirmed for the presence of aldehyde by the presence of a thin layer of silver
on the test tube walls
Test 3
1. 1ml of acetaldehyde was added to a clean test tube.
2. 3ml of 10% potassium iodide solution was added to the test tube.
3. 10ml of sodium hypo chloride solution was added to the test tube.
4. The orange to brown colour change was a confirmation of acetaldehyde in this test.
Results
Before the reaction between ethanol and chromic acid in the reaction flask, in-situ formation of
c chromic acid took place
1. Na2Cr2O7.2H2O + xH2SO4 → yH2CrO4 + zNa2SO4 + H2O
Na2Cr2O7.2H2O + H2SO4 → 2H2CrO4 + Na2SO4 + H2O Equation 1
After this reaction, chromic acid reacted with ethanol and desired product was obtained
2. 3C2H6O + 2H2CrO4 + 6H+ → 3C2H4O + 2Cr3+ + 8H2O Equation 2
Final distillate = 12 ml acetaldehyde
Calculations
Na2Cr2O7.2H2O + H2SO4 → 2H2CrO4 + Na2SO4 + H2O
1 1 2
Moles of H2CrO4
Mr of Na2Cr2O7.2H2O = 297.97g mol-1
Mass of Na2Cr2O7.2H2O used = 25g
Moles of Na2Cr2O7.2H2O = Mass / Molar mass
= 25g / 297.97g mol-1
= 0.083901 mol-1
1 Na2Cr2O7.2H2O : 2 H2CrO4
Moles of H2CrO4 = 0.083901 mol-1 × 2
= 0.167802 mol-1
Density of ethanol = 0.798 g cm-3
Mass of ethanol = volume x density

= 25 cm3 x 0.798 g cm-3
= 19.95 g
Moles of ethanol = Mass / Molar mass
= 19.95 g / 46 g mol-1
= 0.4337 mol
2 mol H2CrO4 ≡ 3mol C2H5OH

So 0.167802 mol of chromic acid would oxidise (3/2) x 0.167802 mol of ethanol.
= 0.251703 mol of ethanol
0.251703 mol < 0.4337 mol(of ethanol)
Chromic acid is the limiting reactant.
3C2H6O + 2H2CrO4 + 6H+ → 3C2H4O + 2Cr3+ + 8H2O
theoretical yield of number of moles for acetaldehyde = (3/2) x 0.167802 mol

= 0.251703 mol of acetaldehyde
Mr of C2H4O = 44.05 g mol-1

Volume of acetaldehyde = 0.251703 mol
Mass = 0.251703 mol x 44.05 g mol-1
= 11.087517 g
Density of ethanal = 0.788 g cm-3
Volume = mass / density
= 11.087517 g / 0.788 g cm-3
= 14.06747 mL
Theoretical yield of acetaldehyde = 14.06747 mL
% yield = Actual yield x 100 / Theoretical yield
= (12 x 100) / 14.06747
= 85.3032%
Theoretical % yield of acetaldehyde = 85.3032%
(National Center for Biotechnology Information , 2021), (National Center for Biotechnology
Information, 2021)
Observations and Precautions
Table 2: colour change observed

Steps in procedure Colour change
Before addition of Na2Cr2O7 Colorless
After addition of Na2Cr2O7 Orange
Before reflux heating Burnt orange
After reflux heating Dark green precipitate
Distillate after reflux heating Colourless
Table 3: colour change in test 2

silver nitrate colourless
Addition of NaOH to silver nitrate Brown precipitate
Addition of dilute ammonia Colourless (precipitate disappears)
Addition of acetaldehyde Silver mirror
Table 4: colour change in test 3

Potassium iodide + acetaldehyde Colourless
Addition of sodium hypochlorite Brown/orange
Precautions
1. Avoid reckless handling and overly close contact with all chemicals used.
2. Lab coat, glasses, gloves must be worn. Hair must be tied up and ankles must be covered.
3. Do not pour waste filtrate( green) in normal tap.
Discussion and Conclusions
• Alcohols classified as primary are those of which the carbon atom bound to the hydroxyl
functional group is covalently bound to another carbon atom. If there is an excess of alcohol,
such as ethanol, it undergoes partial oxidation in the presence of oxidizing agents such as
sodium dichromate to create aldehydes, which can then be distilled down. Moreover, with in
midst of too much oxidizing agent and a reflux heating setup, the aldehyde generated is
further oxidized to its carboxylic acid. Simultaneously, the oxidising agent undergoes
reduction, resulting in the formation of green chromium (III) ions from orange dichromate
(VI) ions, indicating that oxidation has occurred (Elfar, 2019). (New Jersey Department of
Health, 2009)
• Distillation is the method used to separate a mixture of liquids by using the different boiling
points of these liquids. It is based on the evaporation principles. Distillation may also be used
to purify chemicals by causing the elements in a mixture to transition to gaseous states under
varying conditions. As a result, the liquid sample inside the round bottom flask was heated to
temperatures beyond ethanal's boiling point of approximate 23oC but still below ethanol's
boiling point of approximately 78oC in this experiment. The lack of hydrogen bonding
between ethanal molecules may explain its lower boiling point as compared to ethanol. Since
weak intermolecular forces are quickly overcome, a lot less energy or heat is needed. Only
ethanal was allowed to vaporize and penetrate the condenser, where it condensed back to
liquid form before being stored in a separate round-bottom flask. As a result, the ethanal
sample taken out from solution should be said to be pure, as ethanol or other ethanoic acid
that could have been created have significantly higher boiling points than ethanal and are thus
left in the initial flask (Elfar, 2019).
• Test 1. The pH test is taken as acetaldehyde is acidic in nature but, Ethanol is more neutral.
This could assist in the process to conclude that the solution is an aldehyde.
• Test 2. Aldehydes are more ready to bond with other reagent there the formation of the silver
mirror was part of a confirmation that the aldehyde was present because a ketone would not
react.
• Test 3. The precipitate that formed indicated the presence of ethanal. Ethanal is the only
aldehyde that passed the Iodoform test. This test is also known as triiodomethane (Anon,
2020).
References
Anon, 2020. The Triiodomethane (Iodoform) Reaction. [Online]
Available at: https://chem.libretexts.org/@go/page/3921
[Accessed 30 April 2021].
Anon, 2020. Tollens’ Test. [Online]
Available at: https://chem.libretexts.org/@go/page/14967
chemguide, 2015. Making Aldehydes and Ketones. [Online]
Available at: https://www.chemguide.co.uk/organicprops/carbonyls/preparation.html
Elfar, O., 2019. Distilling a product from a reaction (Ethanal). [Online]
Available at:
https://www.researchgate.net/publication/333405503_Distilling_a_product_from_a_reaction_Ethanal
mcdaniel, n.d. Identification of an Unknown: Alcohols, Aldehydes, and Ketones. [Online]
Available at: https://people.chem.umass.edu/mcdaniel/chem269/experiments/aak/procedure.pdf
National Center for Biotechnology Information , 2021. PubChem Compound Summary for CID 702,
Ethanol.. [Online]
Available at: https://pubchem.ncbi.nlm.nih.gov/compound/Ethanol.
National Center for Biotechnology Information, 2021. PubChem Compound Summary for CID 177,
Acetaldehyde. [Online]
Available at: https://pubchem.ncbi.nlm.nih.gov/compound/Acetaldehyde
National Institut On Alcohol Abuse And Alcoholism, 2007. Alcohol Metabolism. [Online]
Available at:
https://pubs.niaaa.nih.gov/publications/aa72/aa72.htm#:~:text=Most%20of%20the%20ethanol%20in
,CHO)%2C%20a%20known%20carcinogen.
National Library of Medicine , 2021. PubChem. [Online]
Available at: https://pubchem.ncbi.nlm.nih.gov/
New Jersey Department of Health, 2009. Harzardeous Substance fact sheet.. [Online]
Available at: https://nj.gov/health/eoh/rtkweb/documents/fs/1695.pdf
organicmystery, n.d. Properties of Aldehydes and Ketones. [Online]
Available at: http://www.organicmystery.com/CarbonylGroup/PropertiesAldehydesKetones.php
Singh, D. S., n.d. Lab Manual-Experiment 3. [Online]
Available at: https://sulis.ul.ie/access/content/group/3ae2b9ce-fbc0-4b43-8baa-
112581e03b81/Lab%20Manual%20and%20files/Experiment%203/Lab%20Manual-
Experiment%203.pdf
[Accessed 29 4 2021].
Post-Laboratory Questions
i. What functional group is characteristic of all aldehydes? Draw the structure

of your product acetaldehyde. List three properties of aldehydes.
Functional group – Carbonyl group

O
||
R–C–H
• Since aldehydes do not form hydrogen bonds with themselves, their boiling point is higher
than that of non-polar compounds (hydrocarbons) but lower than that of related alcohols and
carboxylic acids.
• Due to H-bonding, the lower members of aldehydes (up to four carbons) are soluble in water.
Since the hydrocarbon portion of the higher members is larger and resists the forming of
hydrogen bonds with water molecules, they do not dissolve in water.
• Because to the inclusion of a hydrogen atom on the carbonyl ring, which can be quickly
converted to the OH group, aldehydes can be readily oxidized to carboxylic acids
(organicmystery, n.d.).
ii. What would happen if sodium dichromate was used in excess?
The oxidation of the alcohol will carry on into a carboylic acid if excess of sodium dichromate was
used
iii. As the reaction proceeds there is a colour change from green to orange.
What is this reason for this?
The orange dichromate solution changes to green colour of Cr3+ ions

iv. Why is the acetaldehyde product collected in a flask submerged in ice-water?
This is to prevent the volatile liquid from further evapouration.
v. Describe two sources of error explaining why the yield may not be 100%.
• Some of the ethanal might not have been evaporated into the filtrate.
• Human error could have been a factor, not completely added all the reaction to the round
bottom flask
vi. In this experiment, an aldehyde was prepared via the oxidation of a primary
alcohol. What is the product of the oxidation of a (a) secondary alcohol and
(b) a tertiary alcohol?
• Secondary alcohol – Ketones
• Tertiary alcohol - They cannot be oxidized without breaking the molecule’s C – C bonds.
vii. The oxidation of alcohol (ethanol to acetaldehyde) is an example of a

biological oxidation reaction that occurs in animal cells. It takes place in our
livers. What enzyme metabolises ethanol in our bodies?
• The enzyme is called alcohol dehydrogenase (ADH) (National Institut On Alcohol Abuse
And Alcoholism, 2007).
viii. Aldehydes are responsible for a number of odours in nature. Draw the
structures of and give the common name of the different aldehydes

responsible for the scent of (a) vanilla, (b) cinnamon and (c) almonds.
a. Vanillin - Vanilla
b. Cinnamic aldehyde - Cinnamon
c. Benzaldehyde - Almonds
ix. Our retinas need Vitamin A to produce an aldehyde that is critical to the
process that allows us to have vision. What is the name of this aldehyde?
This aldehyde is called Retinal or Retinaldehyde.

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Organic Chemistry - CH4102

Experiment 3: Preparation of Acetaldehyde

Name: Teniola Abioye Date: 16/04/2021

What are the objectives of this laboratory session?

i. What are your starting reagents?

ii. Draw a structural formula of your starting reagents.

• The most common method of preparing aldehydes is oxidizing primary alcohols.

iv. What is a Silver Mirror Test used for?

v. What is an Iodoform Test used for?

vi. Are any of today’s chemicals considered hazardous?

Long term effects of exposure could be

Table 1 : Equipment and chemicals

Na2Cr2O7.2H2O + H2SO4 → 2H2CrO4 + Na2SO4 + H2O Equation 1

2. 3C2H6O + 2H2CrO4 + 6H+ → 3C2H4O + 2Cr3+ + 8H2O Equation 2

Final distillate = 12 ml acetaldehyde

Density of ethanol = 0.798 g cm-3

Mass of ethanol = volume x density

2 mol H2CrO4 ≡ 3mol C2H5OH

3C2H6O + 2H2CrO4 + 6H+ → 3C2H4O + 2Cr3+ + 8H2O

theoretical yield of number of moles for acetaldehyde = (3/2) x 0.167802 mol

Mr of C2H4O = 44.05 g mol-1

Observations and Precautions

Table 2: colour change observed

Table 3: colour change in test 2

Table 4: colour change in test 3

Steps in procedure Colour change

Discussion and Conclusions

i. What functional group is characteristic of all aldehydes? Draw the structure

Functional group – Carbonyl group

ii. What would happen if sodium dichromate was used in excess?

The orange dichromate solution changes to green colour of Cr3+ ions

iv. Why is the acetaldehyde product collected in a flask submerged in ice-water?

This is to prevent the volatile liquid from further evapouration.

• Secondary alcohol – Ketones

vii. The oxidation of alcohol (ethanol to acetaldehyde) is an example of a

structures of and give the common name of the different aldehydes

b. Cinnamic aldehyde - Cinnamon

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