Then 4. The bromine solution is added slowly with constant stirring to acetanilide solution and the flask is placed in cold water as the reaction is exothermic. When addition of all the bromine is complete the solution turns orange due to the presence of slight excess of bromine, then allowed to stay at room temperature for 30 min. Contents of the flask are poured directly into a beaker having ml ice cold water.

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Home Essays Bromination of Acetanilide Bromination of Acetanilide Topics: Stoichiometry , Ethanol , Oxygen Pages: 3 words Published: February 20, Bromination of Acetanilide Objective: The objective of this experiment was to use melting point and NMR to determine which of two isomers, ortho or para, would most likely form after brominating Acetanilide through electrophilic aromatic substitution.

Then, add 2. Stir the mixture until all of the acetanilide has dissolved. It may be necessary to add more acetic acid dropwise until full dissolution has occured. In the fume hood, add 0. Cap the round bottom flask before returning to the bench.

For minutes, stir the reaction mixture at room temperature so that the reddish-orange coloration will fade and a solid precipitate will form. Return to the hood and add a few more drops of the bromine solution in the hood if all the coloration fades.

Once the reaction is complete, return to the hood. Transfer the mixture to a 25 mL Erlenmeyer flask with 10 mL of water. Rinse the reaction flask out using another 5. Return to the bench to complete the final work-up. Cool the reacting mixture in an ice bath. Collect the solid precipitate using a Hirsch funnel through vacuum filtration.

Wash with ice cold water to complete the transfer. If the crude product is yellow, disconnect the vacuum, add a few drops of the sodium thiosulfate solution, then reconnect the vacuum. Follow with 1 or 2 washings of ice cold water. Dry the crude product minutes using the vacuum. Be sure to dissolve the crude product in the minimal volume of 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. 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



You are on page 1of 7 Search inside document Austin Goewert, Chem Synthetic 3 FFR Bromination of Acetanilide Introduction Electrophilic aromatic substitution is an important practice in organic chemistry because it can be used to add a wide range of functional groups to aromatic rings. One such addition is the bromination of acetanilide to form 4-bromoacetanilide. Acetanilide has many chemical and biological functions including: inhibitor in hydrogen peroxide, rubber accelerator, antiseptic, and precursor to penicillin. This substituent provides resonance stabilization to the carbocations created by ortho and para addition.


Bromination of Acetanilide: Mechanism & Explanation


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