Bromination of Acetanilide

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BROMINATION OF ACETANILIDE

OBJECTIVE

Aim of the experiment was too brominate acetaldehyde to form p-bromoacetanilide.

INTRODUCTION

Acetanilide is a chemical compound with the chemical formula of C6H5NH(COCH3). It is a crystalline solid that is prepared by acetylation of analine and is widely used in the dye industry. This crystalline solid is an odourless solid chemical that has a flake or leaf like appearance. It is also known as N phenylacetamide, acetanil or acetanilide. Its former trade name was antifebrin. As mentioned earlier acetanilide can be produced by reacting acetic anhydride with aniline.

C6H5NH2 + (CH3CO)2O → C6H5NHCOCH3 + CH3COOH

(http://www.mendelset.com/articles/680/preparation-recrystallization-acetanilide)

(regensburg.de/Fakultaeten/nat_Fak_IV/Organische_Chemie/Didaktik/Keusch/Grafik/box_brom_ar1.gif)

The second figure illustrates the process used in the laboratory to form bromoacetanilide. Recrystallization is of key importance in the experiment because this method is used to obtain the crystals. Recrystallization is a purification technique that removes impurities from a sample. An impure solid is placed in a liquid for example water or ethanol. It is then heated making the solid dissolve into the solvent. When the solvent cools back down again, the solid will precipitate out of the solution and leave the impurities behind, still dissolved in the solvent. This method purifies the solid. Acetanilide has many uses in both pharmaceutical and manufacturing industry. It is used as a precursor in the synthesis of penicillin and other pharmaceuticals. Originally it was the first aniline discovered to posses’ analgesic and antipyretic properties. A.Cahn and P.Hepp introduced it in the medical field in 1886. It was later to be discontinued in the medical field because of its toxic nature that was believed to cause cyanosis in the patient. Through further research it was also discovered that acetanilide is metabolized in the...
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