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Experiment - 4: Reduction of P-Nitrophenol To P-Aminophenol

The document describes an experiment to prepare p-aminophenol by reducing p-nitrophenol. Strong reducing agent LiAlH4 is used, which liberates hydrogen upon reaction with TiCl4. This hydrogen then reduces the nitro group of p-nitrophenol to the amino group of p-aminophenol. Yield percentage of a reaction converting p-nitrobenzoic acid to p-aminobenzoic acid is calculated as 65.63%. Mass spectrometry and IR spectroscopy are used to analyze product characteristics. Paper chromatography is demonstrated to separate compounds using a stationary cellulose paper phase and mobile water solvent phase.

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Saketh Ram S 21BLC1562
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87 views

Experiment - 4: Reduction of P-Nitrophenol To P-Aminophenol

The document describes an experiment to prepare p-aminophenol by reducing p-nitrophenol. Strong reducing agent LiAlH4 is used, which liberates hydrogen upon reaction with TiCl4. This hydrogen then reduces the nitro group of p-nitrophenol to the amino group of p-aminophenol. Yield percentage of a reaction converting p-nitrobenzoic acid to p-aminobenzoic acid is calculated as 65.63%. Mass spectrometry and IR spectroscopy are used to analyze product characteristics. Paper chromatography is demonstrated to separate compounds using a stationary cellulose paper phase and mobile water solvent phase.

Uploaded by

Saketh Ram S 21BLC1562
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as DOCX, PDF, TXT or read online on Scribd
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Experiment – 4

Reduction of p-Nitrophenol to p-Aminophenol


Name: Sravan | Register no: 21BLC1018 | Date: 17.3.22

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

Principle:
The reduction reactions in the 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, LiAlH4 liberates hydrogen
gas upon reaction with TiCl4 . The hydrides formed from the interaction of hydrogen gas with TiCl4
reduce the nitro group of p-nitrophenol to p-aminophenol.

Theoretical Question:
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%

To Find the characteristics peaks for the products from the Mass-spectrum and IR spectrum.

Observed mass (M): 120 Observed mass (M+H): 137

As observed from the given spectrum chart, characteristic peaks have been observed in the fingerprint
region,

Chromatography principle:
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. The cellulose paper can well absorb water molecules. 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.

Testing Chromatography at home:

Materials used: compound dye/ink, cellulose paper, water, beaker

Photo of procedure at home:


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

Conclusion:
* Spectrography was done to show the presence of the product via IR and Mass spectrum

* chromatography is a way of seperating various mixed compounds by introducing a moving phase


which in return transports the different compounds to different distances as per their RF values

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