Joe Schmo 4/9/12 Instrumentation Performed on 4/16/12

Experiment 5, Part 2. Synthesis Of 4-Acetamidobenzenesulfonamide Abstract: In this two part lab the student was to perform a synthesis of 4acetamidobenzenesulfonamide by first doing a chlorosulfonation of acetanilide, this reaction occurs when acetanilide is combined with chlorosulfonic acid in the HCl trap which liberates the hydrogenchloride gas. The reaction is rapid and exothermic so an ice bath is used to keep it controlled and the acid is added slowly. Then it is heated gently for ten minutes driving the reaction to completion and put in an ice bath. Cold water is added so that the 4-acetamidobenzenesulfonyl chloride precipitates out as a solid. The product is collected by vacuum filtration. The next part is done during the same lab period to avoid the slow hydrolysis of the 4-acetamidobenzenesulfonyl chloride. The next step in the synthesis of the 4-acetamidobenzenesulfonamide is the ammonolysis of the product in the first part of the procedure. 15mL of ammonium hydroxide are slowly added and the reaction mixture is gently heated. Then the mixture is cooled and the product is collected using vacuum filtration. The student obtained a 16.67% yield, and the TLC test proved to be inconclusive. After analysis of the IR spectrum the student was able to find peaks present in the IR spectrum that include 1662cm-1 which could be from the C=O bond, peaks present in the 3600cm-1 region could be due a N-H bond, multiple peaks in the 1500cm-1 suggest could possibly due to the benzene ring in the 4-acetaminobenzenesulfonamide coumpound.

Data: Weight Of Acetanilide Used Volume of Chlorosulfonic Acid Used 4.1994g 10.5mL

Calculations: Volume of Chlorosulfonic Acid Used: For every 5g of acetanilide use 12.5 mL of Chlorosulfonic Acid, so the ratio then is 12.5/5 = 2.5 4.1994g * 2.5= 10.5 mL Theoretical Yield of 4-Acetaminobenzenesulfonamide (4.1994g) * (1mol acetanilide/135.17g) * (1mol 4-acetamidobenzenesulfonamide/1mol acetanilide) *

(214.24g/1mol 4-Acetamidobenzenesulfonamide) = 6.6559g Percent Yield of 4-Acetaminobenzenesulfonamide 1.1094g/6.6559g * 100% = 16.67%

Discussion: The student determined the yield of the 4-acetamidobenzenesulfonamide product to be 16.67%, possible sources of error that contribute to a low yield could be that some product was lost when transferring to the flask. Also, when performing the filtrations, some of the product stayed behind on the filtration paper. Another source of error could have been adding the chlorosulfonic acid to quickly or not having it cold enough because then the reaction might have occurred too quickly, another source of error could have been boiling the acetanilide and chlorosulfonic acid instead of gently heating it, this could result in a loss of product. The TLC test for purity proved to be inconclusive because there was no difference between the aldehyde and the product which was done three separate times. Also, this was confirmed between the groups performing the lab that the test was inconclusive. The melting point of the product was 214-217 C which was the same as the literature value which confirms that it was the 4acetamidobenzenesulfonamide product. Peaks present in the IR spectrum include 1662cm-1 which could be from the C=O bond, peaks present in the 3600cm-1 region could be due a N-H bond, multiple peaks in the 1500cm-1 suggest could possibly due to the benzene ring in the 4acetaminobenzenesulfonamide coumpound.