You will carry out a simple synthesis of N-benzyl-3-nitroaniline according to the reaction scheme: [ — Physical Chemistry — Kinetics Chemistry Question
Synthesis of N-benzyl-3-nitroaniline
You will carry out a simple synthesis of N-benzyl-3-nitroaniline according to the reaction scheme:
[VISUAL]
Chemicals and reagents
* Meta-nitroaniline, solid
* Benzaldehyde, solid
* NaBH4, solid
* Ethanol, abs.
* Hexane
* Ethyl acetate
Procedure
Dissolve 1.1 g meta-nitroaniline in 10 cm3 of ethanol in a 25 cm3 Erlenmeyer flask and add 1.5 cm3 benzaldehyde to this mixture. Let the flask stand for 20 minutes with occasional shaking. Transfer the flask to an ice-water bath. On cooling a solid material precipitates. Collect it on a sintered glass funnel. You can use the filtrate to wash the solid remaining in the flask onto the filter. Since the product is moderately soluble in alcohol, do not wash it on the filter, just dry it with suction. Set aside a small sample for thin-layer chromatography (TLC).
Place the solid substance into a 100 cm3 Erlenmeyer flask and dissolve it in 20 cm3 of ethanol. Slowly add to this solution 0.5 g of NaBH4 in small portions with constant swirling. Continue swirling the flask for an additional 15 minutes, and then pour its content into 50 cm3 of ice-cold water. Collect the precipitate on a sintered glass funnel and wash with cold water. Dry the product in air and weigh it.
Give the mass of the product.
Make a thin layer chromatogram on a silica plate with hexane/ethyl acetate = 4:1 as eluent and compare the chromatographic properties of the starting materials, the intermediate and the product. Suggest a method for visualization of the spots.
Comment on the purity of the intermediate and the product.