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Sulfonation of Aniline Experiment

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1.

5: Procedure
 A 100 ml beaker was placed with magnetic bar in it, on hot plate.
 12.5g of sodium dichromate was transferred in the beaker and 125 ml distilled water added with
continuous stirring.
 22g sulfuric acid was added to sodium dichromate solution along with continuous stirring.
 The stirring process persisted for a duration of 10 minutes, ensuring optimal blending and
homogeneity.
 Cyclohexanol was poured into a separate conical flask.
 Chromic acid mixture was added to cyclohexanol completely as one part.
 Temperature was maintained between 55-60°C.
 The mixtures were stirred for a period of 30 minutes.
 Distillation was performed to obtain pure product.
 Work up of product was performed by solvent extraction.
 Organic layer was dried with Na2SO4 or MgSO4.
 Dried organic layer was transferred to another flask.
 Percentage yield was calculated.
 1.6: Confirmatory tests
To confirm the presence of cyclohexanone, following test was performed:
2,4 DNPH Test
Aldehydes and ketones form a yellow or red precipitates with ,4-dinitrophenylhidrazine solution.2,4
DNPH reagent was added to solution of cuclohexanone. The mixture was stirred vigorously for several
minutes. After allowing the reaction to proceed for a specific period of time, a distinctive orange or
yellow precipitate was observed, confirming the formation of the 2,4-DNPH derivative.

2,4-dinitrophenylhydrazine Cyclohexanone 2,4-dinitrophenylhydrazone

1.7: Observations and calculations

Substance Quantity(g) Density(gcm-1) Molecular weight Boiling point


(gmol-1) (°C)
Cyclohexanol 12.5 0.96 100.158 161.8

Sodium 25.5 2.52 261.97 400


dichromate
Sulfuric acid 22 1.83 98 337

Cylohexanone ……… 0.947 98.15 155.62

In the experiment, 12g of cyclohexanol was used.


Density of cylohexanol = 1.02 g/ml
Molar mass of cyclohexanol = 100.158
No. of moles of cyclohexanol = 0.1243moles
The reactant to product molar ratio is 1:1.
Cyclohexanol : Cyclohexanone
1 : 1

Number of moles of Cyclohexanone = 1 × 0.1243 moles

= 0.1243moles

From this data, the theoretical amount of cyclohexanone was calculated.

Theoretical yield of cyclohexanone = moles of cyclohexanone × molecular weight


= 0.1243 × 98.15
= 12.2g
Actual yield of cyclohexene = 9.3g

actual yeild
Percentage yield = ×100
theoretical yeild
9.3
¿ ×100
12.2

= 76.23%

1.8: Result

The percentage yield of cyclohexanone was found to be 76.23%

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