STUDENT NAME: Manda Baboolal

STUDENT ID: 816014005

COURSE CODE: CHEM2673

COURSE TITLE: Core Chemistry Laboratory II

DATE: 18/02/20, 03/03/20

DEMONSTRATOR: Thalia

EXPERIMENT #1A AND 1B- MULTISTEP SYNTHESIS OF AN AROMATIC

COMPOUND
PREPARATION OF p-IODONITROBENZENE
 OBJECTIVES

 To perform a multistep organic synthesis.

 To calculate the overall and individual yield of organic multistep synthesis.
 To purify and organic compound using recrystallization technique.
 To determine the purity of p-nitroaniline and p-iodonitrobenzene via TLC and melting
point.
 To interpreting the H-NMR and IR spectra of p-nitroaniline and p-iodonitrobenzene.
 INTRODUCTION

p-Iodonitrobenzene is a diazonium salt with the molecular formula C6H4INO2.

Benzenediazonium salts are used in preparing compounds such as iodoarenes (ArI) and
arenenitriles (ArCN) that are not easily available from electrophilic substitution. In order to
prepare p-Iodonitrobenzene from acetanilide as well as to determine its purity, a series of
reactions are performed:

1. Nitration- This reaction involves adding a mixture of concentrated nitric acid and
sulphuric acid. An electrophilic substitution reaction occurs in which the nitronium ion
acts as the electrophile and attacks the benzene ring. This gives an ortho and para mono
nitroacetanilides. This position of nitronium ion is directed by the –NHCOCH3 group
attached to the benzene ring. This is due to the resonance delocalizing the benzene ring
by nitrogen lone pair. Therefore, Ortho and Para positions are more resonance stabilized
than the Meta. Acetanilide undergoes ready nitration giving mainly the colourless P-
nitroacetanilide, mixed with much smaller proportion of the yellow colour O-
nitroacetanilide.
2. Acid Hydrolysis - p-nitroacetanilide is subjected to hydrolysis of acetate on from
acetamido functional group in the presence of concentrated sulphuric acid to form p-
nitroaniline.
3. Diazotizaton of p-nitroaniline - This is a nucleophilic reaction. It is reversiable due to the
rapid formation of N2 gas.

The following diagram shows the formation of p-iodonitrobenzene:

The outer nitrogen atom of the

diazonium salt is also an
electrophilic site and can serve
as the
electrophilic atom in aromatic
substitution reactions on
activated benzene rings such as
anilines
and phenoxides.
The outer nitrogen atom of the
diazonium salt is also an
electrophilic site and can serve
as the
electrophilic atom in aromatic
substitution reactions on
activated benzene rings such as
anilines
and phenoxides.
The outer nitrogen atom of the
diazonium salt is also an
electrophilic site and can serve
as the
electrophilic atom in aromatic
substitution reactions on
activated benzene rings such as
anilines
and phenoxides.
The outer nitrogen atom of the diazonium salt is also an electrophilic site and can serve as the
electrophilic atom in aromatic substitution reactions on activated benzene rings such as anilines
and phenoxides.

PROCEDURE

Changes were made in Part I of Part A in the experiment. 7ml of concentrated sulphuric acid
were used instead of 5ml. The rest of the experiment were carried out according to page 1.6.

RESULTS
Table 1: Table showing the mass of acetanilide used.

Mass of flask(g) 62.3550

Mass of flask and acetanilide(g) 65.4840
Mass of acetanilide (g) 3.1290

Table 2: Table showing mass of crude p-Nitroaniline obtained.

Mass of vial(g) 7.9230

Mass of vial and p-Nitroaniline (g) 7.9390
Mass of p-Nitroaniline (g) 0.0160

Table 3: Table showing mass of charcoal used.

Mass of beaker(g) 31.8110

Mass of beaker and charcoal (g) 32.3330
Mass of charcoal (g) 0.5220

Table 4: Table showing mass of pure p-nitroaniline crystals obtained.

Mass of vial (g) 9.4310

Mass of vial and crystals (g) 9.9410
Mass of crystals (g) 0.5100

*This mass was used in the diazotization reaction.

Table 5: Table showing mass of sodium nitrite used.

Mass of beaker(g) 32.9523

Mass of beaker and sodium nitrite(g) 33.2057
Mass of sodium nitrite (g) 0.2534

Table 6: Table showing mass of KI used.

Mass of beaker (g) 105.0010

Mass of beaker and KI (g) 106.0940
Mass of KI(g) 1.0930

Table 7: Table showing mass of p-Iodonitrobenzene.

Mass of vial (g) 9.2690
Mass of vial and p-Iodonitrobenzene(g) 10.342
Mass of p-Iodonitrobenzene(g) 1.0730

Table 8: Table showing melting points obtained for p-Iodonitrobenzene and nitroaniline.

Compound Melting Point (oC)

p-Iodonitrobenzene 171-172
Pure nitroaniline 147-148
Crude nitroaniline 147-148