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Pharmaceutical Organic Chemistry Lab 1 PHC464
Pharmaceutical Organic Chemistry Lab 1 PHC464
PREPARED BY :
NAME ID STUDENT
1
2
3
PRACTICAL 1 : Mononitration of Toluene
Objectives
To understand the mono subtitution of Toluene
Discussion
The electrophilic aromatic substitution in toluene is the subject of this experiment.
Methylbenzene was treated with nitric acid, HNO3 and sulphuric acid, H2SO4 to produce the
nitro-substituted toluene. As a result, 2-nitromethylbenzene and 4-nitromethylbenzene are
formed. Thus, sulphuric acid acts as a catalyst to increase the rate of reaction. During the
experiment, precautions must be taken, such as gently swirling the flask containing the
HNO3 and H2SO4 respectively, under running tap water to ensure that it does not cool below
room temperature. Then, the product was collected by filtration before undergoing
recrystallization. The purpose of the recrystallization process is to obtain a pure product that
is free from any impurities.
● Mechanism
In this reaction, the electrophile is the nitronium ion (NO2+), which is produced from
concentrated nitric acid and sulphuric acid.
Toluene is nitrated when the electron-rich benzene ring attacks the nitronium ion.
Methyl is an electron donor and a weakly activating group; hence, it will function as both a
para and ortho director. This is because the resonance form of the carbocation has a close
proximity to the methyl, releasing electrons to make it more stable and conducive to
synthesis. Existing sulfuric acid acts as a catalyst. As methyl is not a substantial side chain,
ortho products will produce more than para products.
● Percentage yield
The percentage yield of the reaction is 47.516%. The reaction carried out in this
experiment results in a low yield which could be due to practical errors during preparation,
solubility factor of the product, and the practical losses during filtration and recrystallisation.
The product (nitrotoluene) solubility may cause product loss depending on agitation
before filtration. Mononitration of toluene produces a mixture of nitrotoluene isomers, where
p- and m-nitrotoluenes are insoluble in water as yellow liquids, but o-nitrotoluene is soluble
although very poorly (0.07g/100mL at 20°C). Some quantity might dissolve when much ice is
added to solidify the product and scraped to break lumps and washed with water. The
dissolved o-nitrophenol is filtered out when the vacuum pump pulls water from the solid
product.
Precautions to minimise product loss include being vigilant for certain specifications
in the experiment procedure that are easily overlooked; such as using the same cylindrical
measure when obtaining HNO3 and H2SO4, and allowing solution to cool (without agitation)
before putting in ice bath. Understanding the importance of each step in the procedure may
help with this precaution. Another precaution is to avoid excessive agitation in water if
product is somewhat water-soluble. Lastly, using a dropper when a substance is supposed
to be added slowly.
Calculation
3.885 g Thus,
= x 100%
= 47.516 %
Conclusion
Nitrotoluene can be prepared from toluene by substituting the methyl group attached
to a benzene ring in toluene with a nitro group, where concentrated H2SO4 is used as
catalyst and starting material. This reaction is an electrophilic aromatic substitution where
nitronium ion NO2+ (electrophile) is attacked by electron-rich benzene ring (nucleophile) in
toluene to form a benzenium ion which will be deprotonated by hydrogen sulfate HSO4-. The
mass of nitrotoluene filtered and collected is 1.846g which is 47.516% yield. This low yield is
due to practical errors during preparation, solubility factor of the product, and the practical
losses during filtration and recrystallisation. Precautions to minimise such loss include
understanding the importance of each step in the procedure, avoiding excessive agitation if
product is in the slightest water-soluble, and using a dropper to add a substance slowly.
PRACTICAL 2 : Esterification
Objectives
Discussion
The synthesis of an ester when a carboxylic acid reacts with an alcohol in the
presence of an acid catalyst is called esterification, involving elimination of water molecule
from a molecule of carboxylic acid and a molecule of alcohol; by removing hydroxyl -OH
group from carboxylic acid and a H atom from alcohol. Catalyst and heat provide energy to
remove -OH from carboxylic acid. The product ester is an organic compound with a pleasant
odour which is poorly soluble in water but highly soluble in nonpolar organic solvents.
Therefore, the reaction mixture will form 2 liquid phases, an organic layer and an aqueous
layer. In this experiment, acetic acid CH3COOH and isoamyl alcohol C5H11OH will react to
yield isoamyl acetate CH3COOC5H11 and water, catalysed by sulfuric acid H2SO4.
CH3COOC5H11 is an ester with a banana-like odour, in which acetate group from acid and
isopentyl group from alcohol is combined by an ester linkage. The reaction was carried out in
a reflux. The condenser prevents loss of volatile reactant (alcohol) and the ester product.
H2SO4 acts as catalyst by increasing rate of reaction by lowering activation energy, and as a
dehydrating agent by removing water to force equilibrium position to the right for greater
yield. Boiling chips in flask provide nucleation sites to prevent bumping or superheating. The
reaction mixture is washed with 5% aqueous bicarbonate solution to neutralise the
unreacted carboxylic acid and H2SO4 dissolved in the organic layer. Anhydrous sodium
sulfate, an adsorbing agent, dries the organic layer by removing traces of water. Complete
removal of water is indicated by formation of big clumps by the anhydrous Na2SO4.
● Mechanism
● Percentage yield
Besides, percentage yield was calculated in this experiment to know how much the
reactant reacts to form ester as the product. In theory, the higher the percentage yield, the
more effective the chemical process. Thus, the percentage yield that we obtained is 69.9%
with the actual mole 0.0321 mole and theoretical mole 0.0459 mole. As a result, we can see
that the reaction may be incomplete as the 30.1% was lost. It is due to experimental error
and improper technique during handling the experiment. For instance, when washing the
mixture, some of the organic layer may be eliminated from the separatory funnel and the
product may also lost when improper transferring the product into Erlenmeyer flask in order
to weigh them.
Calculation
Conclusion
The purpose of this lab was to produce esters from the acid catalyzed reaction
between an alcohol and a carboxylic acid. We were successful in achieving this goal as the
product has dinstict “banana” smell which indicates the presence of esters. The ester
obtained from this experiment is isoamyl acetate via the Fischer esterification method, with a
percentage yield of 69.9 % due to sample loss during the filtration or heating processes.
References
Sandtorv A. (n. d.). 2.1: Recrystallization, as cited in PDX Open publishing initiative.
Retrieved from
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_How_to_be_a_Succe
ssful_Organic_Chemist_(Sandtorv)/02%3A_COMMON_ORGANIC_CHEMISTRY_LABORA
TORY_TECHNIQUES/2.01%3A_RECRYSTALLIZATION
Shammi T., P. S. T. Sai (2009). Esterification of ethanol with sulfuric acid: A kinetic study.
Retrieved from
https://onlinelibrary.wiley.com/doi/abs/10.1002/cjce.5450790109#:~:text=Anhydrous%20sodi
um%20sulfate%20was%20used,water%20formed%20during%20the%20reaction.