Multistep Synthesis Lab Report

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In this experiment, a multistep synthesis was performed, electrophilic aromatic substitution took place, and a protecting group was used. The compound that resulted from the synthesis was sulfaniliamide. In order to get this product, three reactions took place. First, the reaction between acetanilide and chlorosulfonic acid was performed. This reaction resulted in a white powder which was confirmed through IR and 1H NMR to be 4-acetamidobenezenesulfonyl chloride. The IR spectrum, RM-12-Ai, shows an amine group at 3316 cm-1 and 1585 cm-1, a carbonyl at 1679 cm-1, an aromatic carbon-carbon stretch at 1533 cm-1, a sulfone 1372 cm-1 and 1166 cm-1, and a para-substituted ring at 836 cm-1. All of these functional groups are represented in this compound, …show more content…

The product that was recovered was tan, shiny crystals and weighed 0.916 g. The partial percent yield for this step was 45.96 %. This yield was determined by using the amount of 4-acetamidobenezenesulfonamide in this step to calculate the theoretical yield. The amount recovered was then divided by this theoretical yield to the partial percent yield. Once both partial percent yields were determined, the overall percent yield for this multistep synthesis was calculated. The overall percent yield for this experiment is 26.72 %, and was determined by taking the product of 0.4596 and 0.5814, and multiplying it by 100. One reason the overall yield is low, is the constant transferring of materials from one apparatus to another. If the reactions could be performed in one apparatus, the amount of product lost during transfers would be eliminated. Even though there was a low recovery, identification of the final product was confirmed, and tests for solubility were performed. For the solubility test, sulfanilamide was tested with 1.5 M HCl and 1.5 M NaOH. Both test resulted in sulfanilamide being soluble in each solvent. Next, the melting point for the final product was found. The melting point for this compound was determined to be 163-165 ˚C which matches the known value for sulfanilamide. The IR spectrum, RM-12-Ci, also confirms that the reaction was completed. In the IR spectrum, a carbonyl group was not present. This is important because sulfanilamide does not contain this functional group like the previous products. The only functional groups that are present in this spectrum are an amine group at 3551-3239 cm-1, a nitrogen-hydrogen bend at 1596 cm-1, a sulfone at 1305 cm-1 and 1142 cm-1, and a para substituted ring at 824 cm-1. All of the functional groups are found in the product. The 1H NMR spectrum also confirm that

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