Student number: 201933674

Surname and initial: Kabekwa BM

Title of the experiment: Bromoaniline
Date: 21 April 2021
INTRODUCTION
Para-bromoaniline its properties are grey-brown powder shape crystal with a distinctive
odour, commonly used as a chemical precursor in the synthesis of medication, dyestuff, and
other fine chemical materials. In medicine, para-bromoaniline may be used to prepare amine
benzene phosphonic acid class medicine for preventing thrombus formation [1]. A chemical
reaction in which a molecule of water is attached to a surface is known as hydrolysis. When
this happens, both the material and the water molecule will break into two. One fragment of
the target molecule (or parent molecule) gains a hydrogen ion in certain reactions [2]. Bromo
acetanilide can be easily hydrolysed with aqueous HCl. To obtain the desired p-bromoaniline,
the amide group is hydrolysed to the amine. Bromo acetanilide is structurally identical to a
significant number of compounds that alkylate the methionine residue in chymotrypsin to
render it inactive. By carefully applying caustic alkalis or acid to aniline, it was hydrolysed.
When an electrophilic aromatic substitution is involved, several aromatic compounds are
brominated. The conversion of an amino group to an amide and subsequent regeneration
back to an initial amino group from a potential electrophile replacement reaction [3].

Halogenation includes electrophilic aromatic substitution reactions. In a halogenation reaction,

the electrophile (a halogen with a Lewis acid catalyst) attacks the benzene, causing hydrogen
to be substituted. Bromination is one of the most common halogenation processes. As
bromine reacts with a Lewis acid catalyst, it becomes an electrophile, as the name implies.
Bromine reacts with benzene with the aid of a catalyst. Aniline is bromated to make p-
bromoaniline for this experiment. This reaction entails more than just a bromine electrophilic
assault on aniline. The production of unwanted side products is an issue that can occur during
compound synthesis. The development of any undesirable side products can be avoided by
using aromatic safety and deprotection reactions in synthesis. This experiment involves
aniline, an amine group which is an ortho, para-directing group and a very good activator. To
have an amide, by reacting acetic anhydride, an aryl amine such as aniline may be safe.
Deprotection of the amide on the ring is possible by hydrolysis of an acid or a base. The
blocking group will be removed, and p-bromo acetanilide will be converted back to aniline. As
a result, the target compound is obtained: p-bromoaniline [4].

APPARATUS

 Flat flask (100ml)

  Graduated cylinder (50ml)
 Hot plate
 Condenser
 A red litmus papers
 Stirring rod

REAGENT AND SOLUTION

 Bromo acetanilide -2.5g

 HCl -25ml
 Sodium hydroxide

METHOD

The method was followed as outlined on SCHA021 practical manual from page 12 to 13.

RESULTS

BROMOACETANILIDE

N=m/M =2,5g/214,06g/mol

=0,117mol

HCl

Mass = 25ml×1,2g/ml

=30g

N=m/M =30g/36,458g/mol

=0,823mol

Bromo acetanilide is the limiting reagent.

Theoretical yield =2,5×172,02/214,06 =2,0g

Percentage yield =1,43/2,0×100 =71,5%

DISCUSSION
Bromo acetanilide was reacted with HCl, and the solution was heated via a hot plate to
remove the bromo acetanilide as a reflux condenser condensed the steam from the mixture.
A red litmus was added into the solution after being removed from the hot plate, the solution
was highly concentrated and acidic. In the presence of red litmus paper that turned blue
inside the flask, the solution was cooled in an ice bath and sodium hydroxide was applied
slowly to make the solution alkaline. As sodium hydroxide was added and stirred carefully the
reaction was bubbly, vigorous and the product started to form. Then it was later separated by
suction filtration. Since the aromatic ring of aniline is very electron rich due to the tendency of
the lone pair on the nitrogen to be delocalised into the system, it readily undergoes
electrophilic substitution reactions. Aniline can be used to make more complicated products
like acetamide, sulphonic acid, and sulpha medicines. Aniline is converted to N-phenyl
ethanamide, which is then brominated in the 4-position to obtain N-(4-bromophenyl)
ethanamide in this experiment. The amide group is hydrolysed back to the amine after
bromination to create the final product,4-bromoaniline. Hydrolysis reactions use water to
break down polymers into monomers, in contrast to dehydration synthesis, which creates
water when a polymer is synthesized from monomers. Hydrolysis reactions unleash energy by
breaking bonds.

71.5 percent is the theoretical percentage yield. The product's potential yield is 2,0g, but the
true yield is 1,43g. Since recrystallization was not done in this experiment, the theoretical
yield is higher than the real yield. This may be due to impurities. There is a discrepancy
between the recorded melting point of 59°C-62°C and the true melting point of 60°C-64°C,
this may have been because the product was not completely dry.

CONCLUSION

We succeeded in preparing bromo aniline with a melting point of 59°C-62°C by hydrolysis of

bromo acetanilide, which has a melting point of 60°C-64°C. Bromo aniline's colour ranges
from white to brownish.

EXERCISE

MECHANISM
2. The importance of sodium hydroxide is neutralization.

References
[1] "Google Patents," CN201510420134.3A, 15 July 2015. [Online]. Available: https://patents.google.com.
[Accessed 25 04 2021].

[2] "Wikipedia," Google, 16 April 2021. [Online]. Available: https://en.wikipedia.org>wiki>hydrolysis.

[Accessed 25 April 2021].

[3] "Experiment 4- Organic chemistry practical report," StuDocu, 2020/2021.

[4] K. Thompson, "Thompson synthesis of p-bromoaniline," StuDocu, 2020/2021.