PRACTICAL 1

FREE-RADICAL BROMINATION OF p-TOLUIC ACID, FOLLOWED BY NUCLEOPHILIC

SUBSTITUTION REACTION

NAME: MELANE ZINTLE

STUDENT NUMBER :3858078
DATE: 03 MAY 2021
ABSTRACT

The aim of this experiment was to get the α-bromo-p-toluic acid by adding a mixture of p-toluic
acid,NBS and benzoyl peroxide and adding dichloromethane and heat the mixture under reflux. To
get α-methoxy-p-toluic acid the α-bromo-p-toluic acid in methanol is heated under reflux , distilation
takes place then the solution was acidified with HCL and filtered, recrystalise and let product dry and
measure m.p

INTRODUCTION

Free are electrons that contain atleast one unpaired electron, most molecules contain even numbers
of electrons, and the covalent chemical bonds holding the atoms together within a molecule
normally consists of pairs of electrons jointly shared by the atoms linked by the bond. Most radicals
may have been considered to have arisen by cleavage of normal electron pair bonds., every cleavage
having produced two separate entities each of which contains a single, unpaired electron from the
broken bonds.although free radicals contain unpaired electrons they may be electrically neutral ,
because of their odd electrons , free radicals are usually high reactive.

The importance of this practical is to be able to determine α-bromo-p-toluic acid and α-methoxy-p-
toluic acid, to get α-bromo-p-toluic acid

METHOD

p-toluic acid( 2.71g,0.02mole) , NBS (3.6g,0.02moole) were mixed together and benzoyl peroxide
was added as well a. Dichloromethane was added (25ml) in the mixture and the colour changed to
yellow and the mixture was heated under reflux for for I hour with occasional agitation. When the
mixture was heated the colour changed to yellow, and there was evaporation taking place. There
bubbles formed on the going up on the ends /sides of the apparatus and when stirred it kept on
evaporating. Time went by precipitate kept in forming and the colourless steam went up the system
and back to the solution as liquid, precipitate started to sink at the bottom of the liquid. The colour
changed from yellowish to mustard at the centre of the container and became mustard sides of the
container are not as strong as the centre they are light yellow. The mixture is then filtered through
suction and the yellowish thing is left at the filter paper as the product. Water was added on the
product a white precipitate is formed. Potassium hydroxide releases bubbles when heated under
reflux and the that results in dissolving of precipitate. when the solution is put on distillation a
cloudy product is formed, after adding HCL the solution become uniform cloudy no precipitate is
formed, solution was then recrystalized the final product formed was white in colour then the
melting point was measured as well as the yield.

RESULTS

Melting point ranges from 85-97 ℃

α-bromo-p-toluic acid=6.94g

α-methoxy-p-toluic acid 5.58g

theoretical yield=0.04×136.15g/mol

=5.45g

actual yield
the percentage yield = × 100
theoretical yield
 4.54
= ×100
5.45
=82.57%

CONCLUSION

The ojectives of doing this practical were met because at the end of the experiment I have obtained
my product which is white in color I have measured it and submitted with the sticker with my
name. the colour was changing at first after mixing all the given products the colour changed to
yellow but as the aquesous solution was heated the colour changed to mustard and when the
hydrochloric acid was added on the precitate, precipitate dissolved and then the aqueous solution
changed to cloudy while but now the solution was uniform. My product was compromised by
filtration but using hydrochloric acid made me lose a llitle bit of my final product and some
precipitates were filtered on my buchner funnel that’s why I have a little product.

CONCLUSION

The aim of this practical has been reached because I have obtained my mass for α-methoxy-p-toluic
acid which is 4.54g even though a lot of this practical has been lost in the process of making this
experiment.

REFERENCE

1.Jack Hine and Howart W. Hawort J.m Chem.soc.1958,80,9 published date: 1 may 1958

2. Theodore W.Evans,William M. dehn : journal of the American chemical society publisher :

American chemical society 1 jan 1930
3.N.tada ,M.shomura, H.nakayama,T.miura,aA.illtoh, synlett,2010 science of synthesis