Preview

Bromination of acetanilide

Satisfactory Essays
Open Document
Open Document
333 Words
Grammar
Grammar
Plagiarism
Plagiarism
Writing
Writing
Score
Score
Bromination of acetanilide
Bromination of Acetanilide
Introduction:
Bromination of acetanilide to 4-bromoaniline was studied in this experiment. One of the most important mechanism with the reaction of aromatic compounds is the electrophilic aromatic substitution reactions(wade,2013). The electrophilic aromatic substitution enable scientists to make substituted aromatic compounds. However, substitution groups affect the electrophilic substitution mechanism. A nitrogen atom attached to hydrogen is learned to be a powerful activating group, which allow the procedure to go without a catalyst.
The bromination of the acetanilide gives the tribromide instead of 4-bromoaniline. preparing the 4-bromoaniline involves the attack of a strong electrophile and the hydrolysis of a proton to give the final product.

Chemicals and Safety:
Bromine is very poisonous, and can cause burns. Eyes, skin and nose should be protected while carrying the bromine inside the hood.
Glacial acid is also a very corrosive compound and can cause severe burns when it’s reacting with aromatic compounds. Also, the organic waste was disposed in the halogenated waste container.

Procedure:
In a reaction tube, 0.05 g of acetanilide is added and the exact mass is recorded. In the same reaction tube, 8 drops of glacial acid is added carefully inside the hood, and stirred well. Also, 8 drops of bromine in acetic acid is added, and placed for 10 minute in the hood until yellow crystals are forming. Then, 0.5 mL of water followed by 5 drops of sodium bisulfite solution are added to the reaction tube. The reaction tube is placed on an ice bath to cool down and increase the product yield. Then, for vacuum filtration, the product is rinsed with cold water and let it air dried for 5 minutes. The product is then recrystallized by warm 3 mL of 50% ethanol placed on a hot water bath, and the product is cooled down at room temperature. The product is weight and the melting point is recorded. Also, some of the product is mixed

You May Also Find These Documents Helpful

  • Good Essays

    The purpose of the bromination of arenes was to determine the different reactivities of different hydrocarbons with different hydrogen atoms when reacted with bromine under free-radical substitution. The time it took for the bromine color to disappear was used to determine the order of reactivity of the different hydrocarbons.…

    • 869 Words
    • 4 Pages
    Good Essays
  • Satisfactory Essays

    Mechanism 4 shows the debromination of 2α-bromocholestan-3-one to give 4. This mechanism which is similar to a Favoskii rearrangement, is likely to go via this path as other research has shown that there is often a by-product with this reaction. The by-product is cholest-4-en-3-one which requires the intermediate seen in the third molecule in the above mechanism. The intermediate is highly strained and with the presence of base a proton will be extracted which aids the collapse of the three membered ring. To gain the major product, 4, the H1 proton is removed, however it is very possible that the H4 proton is removed instead which would leave the minor product of cholest-4-en-3-one. Both products result in conjugation which will stabilise the molecule. The mechanism for this step is unlikely to go via a simple elimination as for an elimination the eliminated products must be trans to each other for facile leaving. As the bromine is equatorial in both the chair and the boat conformation the bromine is trans with neither of the hydrogens which shows this type of elimination is unlikely to occur. The other possibility is that the acidic hydrogen that is removed in the first step is not H4, but H2. This…

    • 372 Words
    • 2 Pages
    Satisfactory Essays
  • Good Essays

    Also added was 0.45mL water and 0.165mL acetic anhydride and a magnetic spin vane. An air condenser was attached to the vial and it was heated on an aluminum block, with a temperature maintained at 120C. After the solution dissolved, it was heated an extra 20 minutes to allow the reaction to go to completion then cooled back to room temperature. An ice bath was used to encourage crystal growth. The crystals were removed and centrifuged, then placed on a pre-weighed watch glass to dry and weigh. Percent recovery was found. A small sample was set aside for melting…

    • 860 Words
    • 4 Pages
    Good Essays
  • Good Essays

    Oil Of Wintergreen

    • 516 Words
    • 3 Pages

    The solution then gets foggy/cloudy and white snowlike precipitate is floating within the solution. Heat is added along with a stir bar. The stir bar starts stirring at minute 7. It begins to dissolve the white powder as it spins. At minute 26 the solution becomes clear with barely any flakes left. Sulfuric acid is then added and white flakes are formed. More acid is added until the pH paper turns red. The round bottom is filled with white precipitate. The precipitate is put onto a hirsh funnel that uses vacuum filtration to isolate the precipitate. The product is then added to a beaker with D.I water and heated. It’s put through the hirsh funnel . 3.68 grams of salicylic acid is recovered. The melting point is tested to compare to a perfect sample. The melting point is 146C0. The product is dried and added to a beaker with D.I. water and 10mL of acetic anhydride and 20 drops of concentrated sulfuric acid. This product is chilled to produce crystals. Its then filtered using a hirsh filter using vacuum filtration. Recrystallized and filtered one last time. The product is now acetylsalicylic acid…

    • 516 Words
    • 3 Pages
    Good Essays
  • Satisfactory Essays

    Experiment 1 Procedures

    • 537 Words
    • 3 Pages

    From “A Multistep Synthesis Incorporating a Green Bromination of an Aromatic Ring” J. Chem. Educ. 2012, 89, 1063…

    • 537 Words
    • 3 Pages
    Satisfactory Essays
  • Powerful Essays

    Comment on the regioselectivity of the bromination of acetanilide (assign regiochemistry of bromo product - ortho/meta/para, why selective?)…

    • 1196 Words
    • 5 Pages
    Powerful Essays
  • Better Essays

    Experiment 7 Nabr

    • 2251 Words
    • 10 Pages

    1. 1-Butanol and 1-bromobutane are toxic and irritating. Avoid all contact by constantly wearing goggles, gloves and working in the hood. Neither of these compounds can be poured down the drain. Like all products, 1-bromobutane should be turned in to your TA in a labeled vial. Any excess butanol should be discarded in non-halogenated waste.…

    • 2251 Words
    • 10 Pages
    Better Essays
  • Better Essays

    The electrophilic aromatic substitution reaction is the attack of a benzene ring on an electrophilic species resulting in the substitution of a proton with a functional group. The electrophilic aromatic substitution reaction nitration is used to nitrate methyl benzoate and acetanilide with a nitronium ion. Crystallization was used to purify the product. The melting point was used to determine its purity and the regiochemistry of the products. The methyl benzoate reaction product, methyl nitrobenzoate, was determined to be meta-substituted and the acetanilide reaction product, nitroacetanilide, was determined to be para-substituted.…

    • 3498 Words
    • 14 Pages
    Better Essays
  • Good Essays

    Safety issues that were accounted for were that both sodium benzoate and benzoic acid are irritants. Safety goggles were worn and care was taken to ensure that none spilled onto skin or clothes. Hydrochloric acid is a strong acid and is very corrosive. Care was taken not to get any on clothes, skin, or into eyes.…

    • 500 Words
    • 2 Pages
    Good Essays
  • Powerful Essays

    Objective: To perform an electrophilic aromatic substitution reaction, predict the effect on substituent orientation, and determine the identity of the product and mechanism for product.…

    • 727 Words
    • 3 Pages
    Powerful Essays
  • Satisfactory Essays

    Nvq Assignment

    • 428 Words
    • 2 Pages

    | |container – do not store near naked flame, or near |and eyes and do not inhale vapours. Wash hands |appropriate hazard waste…

    • 428 Words
    • 2 Pages
    Satisfactory Essays
  • Good Essays

    8. (10 points) When (R)-4-bromopentanoic acid, 1, is treated with sodium hydroxide, (R)-4hydroxypentanoic acid, 2, is isolated as the only product. Using curved arrows to represent the movement of electrons, write a mechanism for this reaction that explains the formation of the product with particular attention to its observed stereochemistry.…

    • 880 Words
    • 4 Pages
    Good Essays
  • Satisfactory Essays

    This experiment involved the addition of trans-cinnamic acid to bromine for the production of 2,3-dibromo-3-phenylpropanoic acid. This process depicted an electrophilic addition of a halogen to an asymmetrically substituted alkene. A result of this process was the presence of a stereospecific bromonium ion formed by the mechanism of the reaction.…

    • 428 Words
    • 2 Pages
    Satisfactory Essays
  • Good Essays

    To prepare the 2-Bromobutane you must fill a 100 mL round bottom flask with 20 mL of 12M sulfuric acid and 7.4 mL of 2-butanol. Then add 8.0 g of ammonium bromide along with a magnetic stir bar. Then attach the flask to the apparatus, which is mounted on a Thermowell over a stirrer and a condenser attached to it, along with the thermometer in the flask. Then the mixture was heated at 90oC then kept at the range of 90oC-100oC for 30 minutes. When that is completed add 20 mL of water into the flask to perform a simple distillation to collect the distillate in a graduated cylinder, keep doing this until there is no more 2-Bromobutane collected. Use a Pasteur pipette to draw off the organic layer to another container. Add the potassium carbonate to allow the liquid to dry by swirling it.…

    • 762 Words
    • 4 Pages
    Good Essays
  • Good Essays

    Aspirin Lab

    • 648 Words
    • 3 Pages

    for the procedure I prepared a boiling bath using a hot plate, and filled a 400ml beaker with tap water. Then I got a 125ml Erlenmeyer flask and put in 2.00 grams of Salicylic acid using a scale. For the third step I added 5ml of Acetic Anhydride using a graduated cylinder. Then I added 5 drops of concentrated Sulfuric acid to the Acetic Anhydride and Salicylic acid in the Erlenmeyer flask using a dropper. I then heated the flask in the boiling bath for exactly 10 minutes. I then removed the flask and allowed it to cool on the counter for 4.5 minutes while adding 2 ml of cold distilled water dropwise. I then stirred to mix the contents. I Then added 40ml of distilled water in the solution and stirred until crystals began to form. My crystals formed in a matter of seconds. I then put the flask in a 400ml beaker of ice water to cool it down from room temperature for exactly 10 minutes to complete the crystallization process. I then collected the product in a filtration process by using filter paper and washing out the flask with distilled…

    • 648 Words
    • 3 Pages
    Good Essays