Practical 2

23 February 2011
Student no. 210508229
Student name: Ashmika Singh

Hydrolysis of p-nitroacetanilide

Aim:
1. To conduct a hydrolysis of p-nitroacetanilide
2. To determine if the hydrolysis was effective by performing a TLC analysis of the hydrolysed
p-nitroacetanilide and comparing it to isomers of nitroacetanilide

Reaction mechanism:

Rf values:

p-nitroaniline:

Rf: Distance travelled by compound spot (mm)

Distance travelled by solvent front (mm)

23.5/58.5 = 0.40

o-nitroaniline:

Rf: Distance travelled by compound spot (mm)

Distance travelled by solvent front (mm)

43.5/58.5 = 0.74
m-nitroaniline:

Rf: Distance travelled by compound spot (mm)

Distance travelled by solvent front (mm)

32.5/58.5 = 0.56

sample: p-nitroaniline:

Rf: Distance travelled by compound spot (mm)

Distance travelled by solvent front (mm)

24/58.5 = 0.41

Conclusion:
Since the Rf of the sample and the p-nitroacetanilide are within a 0.1 difference in values, it can be
concluded that they are very similar in chemical composition hence the hydrolysis was effective, it
can therefore be said that the p-isomer was produced in the reaction. Traces of the o- and m-
nitroaniline were also present suggesting that recrystallisation was not carried out correctly.