1 acetophenone was converted to benzoic acid using the haloform reaction during the reaction a s

Name: 1 acetophenone was converted to benzoic acid using the haloform reaction during the reaction a student did not have adequate time during the lab period to let the reaction mixture stir long 49541
Uploaded: 2022-05-30T05:03:11-08:00
Duration: 4 min 16 s
Channel: Maitreya E
Description: 1 acetophenone was converted to benzoic acid using the haloform reaction during the reaction a student did not have adequate time during the lab period to let the reaction mixture stir long 49541

1 acetophenone was converted to benzoic acid using the...

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A SYNTHESIS OF BENZOIC ACID Benzoic acid will be prepared using the haloform reaction between molecular chlorine and acetophenone under basic conditions. The chlorine will be generated in situ from common household bleach (aqueous sodium hypochlorite). The crude benzoic acid will be isolated by suction filtration after acidification of the reaction mixture. The benzoic acid will be recrystallized, and its purity will be assessed by measuring the melting point, and by IR spectroscopy. Prelab Prepare for the experiment by tabulating the physical properties; i.e., characteristics such as state, colour, melting point/boiling point/density and solubility in water and organic solvents, as well as any hazardous or toxic properties of the of all reactants, reagents, solvents, products and byproducts that will be encountered during the procedure. Write the balanced reaction for the equilibrium between molecular chlorine and hypochlorite ion in bleach (a basic solution). Calculate the theoretical yield of benzoic acid, given that the concentration of hypochlorite ion in the bleach solution is approximately 0.70 M. Show all of your calculations. Review the mechanism of the haloform reaction so that you understand the role of each reactant used. Acetophenone will be converted into benzoic acid; however, because bleach is strongly basic, the benzoic acid formed will immediately react to form the soluble benzoate anion. The addition of sulfuric acid (the workup step) both neutralizes the excess hydroxide ion from the bleach and protonates the benzoate anion to form benzoic acid. The aromatic ring of acetophenone is deactivated to electrophilic substitution by the acetyl group, and by running the reaction at room temperature, any side reactions involving chlorination of the aromatic ring will be minimized. Procedure All steps up to the isolation of the crude product must be done in the fume hood. 1. Place a magnetic stirring bar and 60 mL of the bleach solution into a 250 mL Erlenmeyer flask. Gently clamp the flask in place after putting it onto a magnetic stirrer in the fume hood. Turn on the stirrer and add 1.5 mL of acetophenone. 2. The temperature of the solution will gradually rise (record the maximum value) as the reaction proceeds, and the yellow colour should gradually disappear. Allow the reaction to stir for a total of 30 minutes.

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Transcript

00:01 Hello students, let's discuss a problem that involves a very important reaction of the organic chemistry and this reaction is called as haliform.

00:10 Acetaphenone is converted into benzoic acid via halloform reaction and the volume and the density of the acetaphenone has been given and we have to calculate the mass of benzoyic acid that has been formed.

00:24 For this it is required to know what is called as halloform reaction.

00:28 Haliform reaction.

00:31 Halliform reaction is a reaction in which a compound, any compound, that is having methyl ketone, that is cs3 -co group this much, undergoes when it is treated with halogen in the alkaline medium.

00:51 Where the halogen could be fluorine, chlorine, bromine, or iodine.

00:58 When iodine is taken, then we get precipitate and this precipitate at chi -3, it is yellow in color and it is called as iodiform.

01:11 In this reaction, when we plan the scheme for this reaction, at the very first step, acetaphenone, when it is treated with halogen, and we are taking the halogen as iodine in the alkaline medium...

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