CHM457 FUNDAMENTAL ORGANIC CHEMISTRY

EXPERIMENT 1 :

ACID-BASE EXTRACTION

NAME NURUL ANIQAH BINTI SAIFUL ADLI

MATRIX NUMBER 2020827822
GROUP CLASS RAS2451A
DATE OF EXPERIMENT 21/10/2020
DATE OF SUBMISSION 25/11/2020
LECTURER’S NAME PUAN SYARIFAH NURSYIMI AZLINA BINTI SYED
ISMAIL
TITLE

Experiment 1 : Acid-Base Extraction

OBJECTIVE

I. To separate two compounds from an unknown mixture.

II. To purify the unknowns by recrystallization.
III. To analyze and identify the compounds by melting point determination.

APPARATUS

I. 125 ml Erlenmeyer flask

II. 125 ml separatory funnel
III. Weighing balance
IV. Hot water / steam bath
V. Melting point apparatus
VI. Litmus / pH paper
VII. Pasteur pipet

APPARATUS SETUP

Ring Stopper
stand

125 ml separatory
flask
Funnel tap

125 ml Erlenmeyer
flask
QUESTIONS

a) What is the melting point of benzoic acid?

The melting point of benzoid acid is between the range 121-123 °C.

b) If the melting point of unknown benzoic acid is differing than a literature stated,
what does it indicates about the purity of that benzoic acid? Does it highly pure or
less pure?

A pure benzoic acid has a melting point at the range of 121-123 °C. When the melting
point is different than the literature state, we can say that the unknown benzoic acid was
contaminated with an impurity. Thus, the unknown benzoic acid is less pure.

c) What is suggested step to overcome problem in Question 2?

 Benzoic acid is dissolved in a minimal amount of a hot solvent or water bath.

 Add a drop of HCL solution.
 The solution is allowed to cool in an ice bath until the compound precipitates, or
"re-crystallizes," from a super-saturated solution.

d) What is the used of adding anhydrous sodium sulphate in any organic reaction?

Anhydrous sodium sulphate is use as a drying agent. By adding the anhydrous sodium
sulfate,it will removes the water by forming the sodium sulfate hydrate, which
conveniently is also a solid allowing it to be filtered away.

e) Why is it wrong to leave a bottle of anhydrous sodium sulphate or calcium chloride

open?

This is because the air in surrounding contain of water. When the bottle is opened, it will
expose the anhydrous to absorb the water particles in the air and this will affect the
anhydrous effectiveness during experiment.

REFERENCES

Haynes, W.M. (ed.) CRC Handbook of Chemistry and Physics. 91st ed. Boca Raton,
FL: C RC Press Inc., 2010-2011, p. 3-38. Retrieved from
https://pubchem.ncbi.nlm.nih.gov/compound/Benzoic-acid#section=Melting-Point.

Dr. Donald L. Robertson. (2012, November 14). Separation of solids : Recrystallization

and melting points. Retrieved from http://home.miracosta.edu/dlr/210exp1b.htm.

Bacher, B. (2016, March 21). Drying agent. Retrieved

from https://www.chem.ucla.edu/~bacher/Specialtopics/Drying%20Agents.html.
 CHM457 FUNDAMENTAL ORGANIC CHEMISTRY

EXPERIMENT 2 :

PREPARATION OF 4-METHYLCYCLOHEXENE FROM

DEHYDRATION OF 4-METHYLCYCLOHEXANOL

NAME NURUL ANIQAH BINTI SAIFUL ADLI

MATRIX NUMBER 2020827822
GROUP CLASS RAS2451A
DATE OF EXPERIMENT 28/10/2020
DATE OF SUBMISSION 25/11/2020
LECTURER’S NAME PUAN SYARIFAH NURSYIMI AZLINA BINTI SYED
ISMAIL
TITLE

Experiment 2 : Preparation of 4-methylcyclohexene from dehydration of

4-methylcyclohexanol

OBJECTIVES

I. To perform an acid-catalyzed dehydration of 4-methylcyclohexanol to produce

4-methylcyclohexene.

II. To conduct a saturation test to test the presence of 4-methylcyclohexene.

APPARATUS

I. 25mL receiving flask

II. Distillation flask
III. Bunsen burner
IV. Thermometer
V. Liebig condenser
QUESTIONS

a) Calculate the theoretical mass of the product 4-methylcyclohexene.

1 mol 4-methylcyclohexanol ≡ 1 mol 4-methylcyclohexene

Molar mass of 4-methylcyclohexanol = 114.2g/mol

Molar mass of 4-methylcyclohexene = 96.2g/mol
9.9736g
Nmol of 4-methycyclohexanol =
114.2g/mol
= 0.0873 mol

Mass of 4-methylcyclohexene = 0.0873 mol x 96.2g/mol

= 8.398g

b) Calculate the yield of the product if 4.55 g of 4-methylcyclohexene was produced

experimentally.
mass(g)
Mol =
molarmass(g/mol)

= 4.55g
114.2g/mol
= 0.0398mol

 0.0398mol of 4-methylcyclohexene was produced.

c) What is the purpose of the simple distillation?

The purpose of simple distillation are to purify the drinking water of unwanted
chemicals and minerals such as salt. The second one is to purify a compound by
separating it fro a non-volatile or less-volatile material.

d) What is the role of the condenser in the distillation?

Condenser is used to condense a compounds in the vapor (gas) phase back down to
the liquid phase under boiling conditions. It allows one to boil a chemical reaction or
a mixture of liquids without evaporating off all of the liquids inside the flask.

e) Why saturated NaCl (brine) is used to wash the distillate (crude 4-

methylcyclohexene)?

The saturated NaCl (brine) is used to dissolve the aqueous solution of cyclohexanol
and water which may be left in the distillate. Beside that, water and cyclohexene
have the same density. By adding NaCl (brine), the water will be more dense than
cyclohexene so that the aqueous solution will lie underneath the organic layer.
 f) What is the purpose of using anti bumping granules during distillation?

The anti bumping granules is used to prevent the mixture from boiling actively
because of the large bubbles that formed from the superheated vapour which break
out suddenly from the mixture or called as bumping. The anti bumping granules have
an air-filled porous surface which will helps the mixture to form a tiny and steady
bubbles when it is heated instead of forming the large bubbles.

g) Give the expected observation when alkene is tested with the following reagents:
i) Bromine in CCl4

The original red-brown colour in bromine will decolourised because of the double
bond that breaks and bromine atom attached to each carbon.CCl₄ is act as a solvent
and it does not effect the reaction between bromine and alkene. It is used to
distinguish between this reaction and the reaction of bromine that used water as the
solvent where the product formed is bromohydrin.

ii) KMnO4 solution

The reaction of alkene with potassium manganate (VII) solution will cause the
colour changing and it depends whether the KMnO₄ solution is in basic or acidic
condition.In acidic condition of KMnO₄ solution where the KMnO₄ is acidified
with dilute sulphuric acid, the purple colour of KMnO₄ will turned into colourless
solution.When the KMnO₄ solution is in basic condition where it usually added
with sodium carbonate solution, the purple solution will initially become dark
green and the solution eventually produces a dark brown precipitate.

REFERENCES

Clark, J. (2016, March). ALKENES and POTASSIUM MANGANATE(VII). Retrieved from

chemguide.co.uk: https://www.chemguide.co.uk/organicprops/alkenes/kmno4.html

Clark, J. (2019, June 6). Reactions of Alkenes with Bromine. Retrieved from Chemistry
LibreTexts:
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Org
anic_Chemistry)/Reactions/Addition_Reactions/Electrophilic_Addition_Reactions/Reactio
ns_of_Alkenes_with_Bromine

Organic techniques. (2012). Retrieved from http://new.chemistry-teaching-resources.com/:

http://new.chemistry-teaching-resources.com/Resources/ADVH/RevisedADVH/Organic%
20Techniques.pdf
 CHM457 FUNDAMENTAL ORGANIC CHEMISTRY

EXPERIMENT 3 :

PREPARATION OF 1-BROMOBUTANE
FROM 1-BUTANOL

NAME NURUL ANIQAH BINTI SAIFUL ADLI

MATRIX NUMBER 2020827822
GROUP CLASS RAS2451A
DATE OF EXPERIMENT 04/11/2020
DATE OF SUBMISSION 25/11/2020
LECTURER’S NAME PUAN SYARIFAH NURSYIMI AZLINA BINTI SYED
ISMAIL
TITLE

Experiment 3 : Preparation of 1-bromobutane from 1-butanol

OBJECTIVE

I. To produce 1-bromobutane from 1-butanol

II. To find the percentage yield of 1-butanol

APPARATUS

I. 25mL round bottom flask

II. 100mL round bottom flask
III. Pasteur pipetes
IV. Boiling stones
V. Distillation setup
VI. Reflux apparatus
QUESTIONS

a) State the function of sulphuric acid in the experiment?

The function of sulphuric acid in this experiment are to increase the amount of
protonated alcohols that present in the reaction mixture and to tie up the water
molecules that generated in the reaction shifting the equilibrium in favoir of the alkyl
bromide.

b) What is the purpose of connecting the glass tube to the beaker of water?

The purpose is to circulate the water through the space between inner and outer layer.

c) How to identify that the layer is organic?

The way to identify that the layer is organic is by adding the distilled water into the
funnel. Whichever layer that increase in size must be the aqueous layer and the other is
organic layer.

d) Calculate the percentage yield from the given information:

Molar mass of 1-butanol = 136.904

Mass of sodium bromide = 17.0405 g
Actual yield = 1.8992 g
 e) Show the step-by-step of reactions mechanism on the formation of 1-bromobutane
from 1-butanol.

REFERENCES

PennState Behrend Chemistry. Chem 213 Synthesis Experiment. Retrieved from

http://chemistry.bd.psu.edu/jircitano/CHEM%20213%20E10%20SN2.pdf

Williamson, Minard & Masters. SYNTHESIS OF 1-BROMOBUTANE : Experimental

procedure at macroscale. Retrieved from
http://educa.fc.up.pt/documents/1_bromobutane_protocol_macroscale.pdf

Faizzarul. (2016). Preparation of 1-bromobutane. Retrieved from

http://fareastzareul1994.blogspot.com/2016/03/preparation-of-1-bromobutane.html
 CHM457 FUNDAMENTAL ORGANIC CHEMISTRY

EXPERIMENT 4 :

PREPARATION OF ACETYLSALICYCLIC
ACID(ASPIRIN)

NAME NURUL ANIQAH BINTI SAIFUL ADLI

MATRIX NUMBER 2020827822
GROUP CLASS RAS2451A
DATE OF EXPERIMENT 11/11/2020
DATE OF SUBMISSION 25/11/2020
LECTURER’S NAME PUAN SYARIFAH NURSYIMI AZLINA BINTI SYED
ISMAIL
TITLE

Experiment 4 :Preparation of Acetylsalicylic Acid (Aspirin)

OBJECTIVE

I. To synthesize Acetylsalicyclic Acid(Aspirin)

II. To measure the synthesized aspirin’s purity

APPARATUS

I. 100mL Erlenmeyer flask

II. Filter paper
III. Buchner funnel
IV. Rubber disk

QUESTION

a) State the function of sulphuric acid in the experiment?

The function of sulphuric acid in this experiment is act as a dehydrating agent.

b) Show the step-by-step of reactions mechanism on the formation of acetyl salicyclic

acid upon reacting salicylic acid with acetic anhydride in acidic condition.
c) Calculate the actual yield of product from the given information:

Amount of salicylic acid used = 2.0 g

Volume of acetic anhydride used = 10 ml
Isolated product yield = 86%
Actual yield of acetyl salicylic acid isolated = ……………...g

Molar mass of salicyclic acid = 138.122g/mol

Molar mass of acetic anhydride = 102.089g/mol

No of mol = (2.0g x 138.122g/mol) / (102.089g/mol)

= 2.7059g
 Percentage yield = (Experimental yield/Theoretical yield) x 100

86% = (2.7059g / Actual yield) x 100

Actual yield = 0.4297g

d) Explain briefly how to conduct proper recrystallization process.

The recrystallization process involved five major steps which are dissolving the solute
in the solvent, performing a gravity filtration, if necessary the crystals of the solute
can be obtained. Then, collecting the solute crystals by the vacuum filtration and
finally drying the resulting crystals.

e) Confirmation of the product (aspirin) as compared to starting material of

salicyclic acid can also be tasted using Ferric chloride. Explain this statement.

This statement explained that ferric chloride test was used to compare the salicyclic
acid, crude aspirin and also purified aspirin. After addition of ferric chloride, the
salicyclic acid solution turns into purple colour. Both of the aspirin turned into yellow.
This is because both of the aspirin solutions were yellow, so there was no any
unreacted starting material present in the product.

REFERENCES

Wired Chemist. Recrystallization. Retrieved from

http://www.wiredchemist.com/chemistry/instructional/laboratory-tutorials/recrystalli
zation

Concept / Skills Development. Activity 1: Synthesis of Aspirin. Retrieved from

http://intro.chem.okstate.edu/ChemSource/medicine/lab1.html

Essays, UK. (November 2018). Synthesis and Recrystallization of Aspirin | Lab Report.
Retrieved from
https://www.ukessays.com/essays/biology/the-synthesis-of-aspirin-biology-essay.ph
p?vref=1
 CHM457 FUNDAMENTAL ORGANIC CHEMISTRY

EXPERIMENT 5 :

NITRATION OF METHYL BENZOATE

NAME NURUL ANIQAH BINTI SAIFUL ADLI

MATRIX NUMBER 2020827822
GROUP CLASS RAS2451A
DATE OF EXPERIMENT 18/11/2020
DATE OF SUBMISSION 25/11/2020
LECTURER’S NAME PUAN SYARIFAH NURSYIMI AZLINA BINTI SYED
ISMAIL
TITLE

Experiment 5 : Nitration of Methyl Benzoate

OBJECTIVE

i. To prepare and calculate the percentage yield of methyl m-nitrobenzoate by

electrophilic aromatic substitution.

ii. To get the melting point of the product.

APPARATUS

I. Water condenser
II. Conical vial
III. Spine vane
IV. Hot plate
V. Sand bath
VI. Thermometer
QUESTION

a) Identify nucleophile and electrophile from the experiment.

Nucleophile : Sulfuric acid (donate a proton to nitric acid)

Electrophile : Nitric acid form nitronium ion

b) Show the step-by-step of reactions mechanism on the formation of nitro

methylbenzoate from the reaction.
c) Calculate the percent yield of the reaction if the following parameter are being
used or observed:

Amount of methylbenzoate used = 5.0 g

Volume of sulphuric and nitric acid used = excess
Isolated product yield = 3.5 g

C6 H5 CO2 CH3 + H2 NO3 → C6 H4 CO2 CH3 NO2 + H2 O

Molar mass of C6 H5 CO2 CH3 = 136.1487 g/mol

5.0 g
Mole of C6 H5 CO2 CH3 =
136.1487 g/mol
= 0.0367 mol

1 mole of C6 H5 CO2CH3 ≡ 1 mole of C6 H4 CO2 CH3 NO2 .

0.0367 mol of C6 H5 CO2 CH3 ≡ 0.0367 mol of C6 H4 CO2 CH3 NO2

Molar mass of C6 H4 CO2 CH3 NO2 = 181.1455 g/mol

Theoretical yield of C6H4 CO2 CH3 NO2 = 0.0367 mol 181.1455 g/mol
= 6.65 g

3.5
Percentage yield (%) = 100
6.65
= 52.63 %

c) Explain why the isolated product yield is less than expected.

The isolated product yield is less than expectation due to the chemical equilibrium
where the limiting reagent may not be completely consumed. Thus, a lower yield is
expected in some cases. Losses during the recovery process of the product will cause
an even lower actual yield.

d) Explain briefly why the experiment was conducted at a very low temperature of
less than O °C

The experiment needs to be conducted at very low temperature because nitration is

consider as a rapid reaction which is 25 times faster than other reaction. Thus, low
temperature is applied to avoid more than one nitro group substituted during the
reaction.
 e) Explain why the final wash of the crystal product need to be tested with pH
paper.

The final wash of the crystal needs to be tested with pH paper to ensure that the traces
of acid are completely removed.

f) Suggest a simple method to prove that the collected crystal is nitro methyl
benzoate.

The collected solid is washed by a cold ethanol and the solid can be recrystallized from
the ethanol. This method proved that the solid is the purified yield.

REFERENCES

Nitration Methyl Benzoate. Retrieved from

https://chemistry.missouri.edu/sites/default/files/class-files/nitration-of-methyl-benzoate.p
df

Sciencing. How to Calculate an Isolated Yield. Retrieved from

https://sciencing.com/calculate-isolated-yield-6946583.html

UKESSAYS. (2017). Nitration of Acetanilide and Methyl Benzoate. Retrieved from

https://www.ukessays.com/essays/chemistry/nitration-acetanilide-methyl-benzoate-2171.p
hp

Nitration of benzene and methyl benzene. Retrieved from

https://www.chemguide.co.uk/organicprops/arenes/nitration.html