EXPERIMENT 4

Reduction of p-Nitrophenol to p-Aminophenol

Name: S.Saketh Ram Reg.No: 21BLC1562

Experiment No: 4 Date: 19/03/2022

Aim: Preparation of p-aminophenol by reduction of p-nitrophenol.

•Calculating the yield of the reaction and confirming the product by analytical data.

Principle: The reduction reactions in organic synthesis are generally referred to as the removal
of oxygen or the addition of hydrogen atoms. In this regard, there are numerous reagents and
catalysts available for the reduction reaction. In this reaction, initially, the strong reducing agent,
LiAlH4liberates hydrogen gas upon reaction with TiCl4. The hydrides formed from the
interaction of hydrogen gas withTiCl4reduce the nitro group of p-nitrophenol to p-aminophenol.
1) Question (Theoretical):
0.03 mol of the p-Nitrobenzoic was used to synthesis of p-aminobenzoic acid. At the end of
the reaction, 2.7g product was synthesized. Calculate the yield of the product in
percentage?

Molar mass of Nitrobenzoic acid: 167.11 g/mol

Molar mass of Aminobenzoic acid: 137.13 g/mol

0.03 mol of Nitrobenzoic acid: 0.03 * 167.11 = 5.0133 g

theoretical yield: (137.13 * 5.0133)/167.11 = 4.1139 g

Actual yield: 2.7 g

therefore, yield percentage: 2.7/4.1139 * 100 = 65.63%

I. Find the characteristics peaks for the products from the Mass-spectrum and IR
spectrum.
Blue Box represents the observed mass= 120(M)
Red Box represents the observed mass=137(M+H)

Principle of Chromatography
The mode of separation of paper chromatography is by partition and the basis for the separation
is solubility. Similar to other chromatographic techniques, her also a stationary phase as well as a
mobile phase exist. Stationary phase is the water that is tightly bound to the paper. The mobile
phase is a developing solution that travels up the stationary phase, carrying the samples with it.
Filter papers are used for this purpose and the most common filter paper used is Whatman filter
paper- 98-99% Alpha cellulose. Cellulose paper can absorb water molecules well. Fiber of
cellulose acts as the stationary phase. Paper chromatography is usually used for separating amino
acids and anions and also testing histamines and antibiotics.
Calculating of RF:

Distance of each marking from origin:

Solvent front (d) : 30mm
top edge (a) : 25mm
bottom edge (b) : 14mm
Therefore:
RF top = (a)/d = 25/30 = 0.8333
RF bottom = (b)/d = 14/30 = 0.4666
RF center = [(a + b)/2] / d = 0.65
Result:
The RF value of the tested ink is 0.65