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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 mnitroaniline were also present suggesting that recrystallisation was not carried out correctly.
