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Patricia S. Duban, Leonard S. Ejipto, Ma. Andrea M. Escamilla, Rebecca Mae M. Gabriel, and Chantal Dana A. Galang Group 4 2B Medical Technology Organic Chemistry Laboratory

This experiment was conducted in order to synthesize acetanilide by acetylation of aniline and to purify crude acetanilide product by recrystallization. Recrystallization is a process of dissolving the solid to be crystallized in a hot solvent or solvent mixture and cooling the solution slowly. The solid used in this experiment was acetanilide, a product formed by the reaction of aniline and acetic anhydride. In this experiment, the crude acetanilide weighing 6.5 grams was dissolved in a beaker containing the recrystallizing solvent. Water was used as the recrystallizing solvent because it is where acetanilide is soluble in high temperature. The mixture was heated in a water bath in order to dissolve the acetanilide. Charcoal was added in the solution in order to absorb the colored impurities present. Upon heating, the solution was filtered in a fluted filter paper and the filtrate was allowed to cool. The crystals were collected, washed with distilled water, dried by pressing in-between filter papers, and weighed. The weight of the pure acetanilide was 1.6 grams and its melting point was 113-115C. The percentage yield of acetanilide was computed by getting the quotient of the weight of pure acetanilide and the weight of the crude acetanilide and dividing the result to one hundred. The percentage yield of acetanilide in this experiment was 24.6%.

Experiment 4 is about recrystallization. The goals of this experiment are to synthesize the acetanilide by the acetylation of aniline and to purify crude acetanilide product by recrystallization. Recrystallization is the primary method for purifying solid organic compounds. Compounds extracted from natural products almost always contain impurities which may include insoluble, soluble, and colored impurities. In order to obtain a pure compound, these impurities should be removed through the process of recrystallization [1]. In order to understand well recystallization, solubility behavior should first be considered. It states that compounds having similar structural features such as polarity and the ability to bond with hydrogen are soluble with one another [2]. In this experiment, acetanilide which is the product of the reaction between aniline and acetic anhydride is purified and tested. Aniline is an organic base used to make dyes, drugs, explosive, plastics, and photographic and rubber chemicals [3].

molecule with an amino group. It boils at 184C and melts at -6C [4]. Acetic anhydride (C4H6O3) is a colorless liquid with a characteristic sharp odor. It is used in making plastics, drugs, dyes, perfumes, explosives and aspirin [5]. B. Procedure 1. Choosing the recrystallizing solvent Three test tubes containing 1mL of water, methanol, and hexane respectively were prepared. In each of the three test tubes, a corngrain amount of pure acetanilide was placed. Every test tube was shook and placed in a warm water bath (37-40C). The observations during room
temperature, heating, and upon cooling were recorded.

2. Preparing the crude acetanilide In an Erlenmeyer flask, 2mL of aniline, 20 mL of distilled water and 3mL of acetic anhydride were mixed. The solution was put in a ice bath, filtered through a wet filter paper, dried and weighed. 3. Recrystallization proper In a beaker,

A. Compounds tested Aniline and acetic anhydride. Aniline (C6H5NH2) is a colorless, oily, basic liquid organic compound. Chemically, it has a primary aromatic amine whose molecule is formed by replacing one hydrogen atom of a benzene

capillary tubes. The substance was not well packed and the capillary tube contained small air packets that caused the uneven heating of the substance. REFERENCES [1] Lenntech. (2012). Sublimation. Retrieved July 28, 2013 from <http://www.lenntech.com/chemistry/sublimatio n.htm#ixzz2aK2rNdDf>

http://www.hartnell.edu/faculty/shovde/chem12a/labl ecturehandouts/recrystallizationlecture.htm RESULTS AND DISCUSSION

From the 5g of impure benzoic acid, 0.8g of sublimate was collected. The percentage recovery was 16%. This means that there was 16% benzoic acid present in the impure sample.

http://www.erowid.org/archive/rhodium/chemistry/eq uipment/recrystallization.html http://global.britannica.com/EBchecked/topic/25473/a niline http://education.yahoo.com/reference/encyclopedia/e ntry/aniline

% Sublimate recovered = = = 16%

x 100

x 100

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The sublimate was grinded and packed into a capillary tube. Pure benzoic acid was also packed into another capillary tube. These were subjected to an oil bath for melting point determination. Table 1 shows the temperatures at which the substances started to melt (Ti) and when the substances were completely melted (Tf). The sublimate was observed to have started melting at 1060C, and was completely melted at 1140C. The pure benzoic acid was observed to have started melting at 1100C, and was completely melted at 1160C.
Substance Sublimate Pure benzoic acid Ti 106 0C 1100C Tf

1140C 1160C

Table 1. Melting point determination data It was observed that the melting point range of benzoic acid in this experiment was 110-1160C, a very far deviation from the standard melting point of pure benzoic acid, which is 1220C. One probable cause of this error might be the improper packing of the substance into the