Grignard Reaction: Benzoic Acid Kenneth Stack Partner: Kelly Adams Lab performed 2/6/14 The experimental purpose

of this lab is to use a Grignard reagent to synthesize benzoic acid. The educational purpose is to learn to use a Grignard reagent for synthesis of benzoic acid. A Grignard reagent is used to react with carbon dioxide in an ether environment to create a carboxylic acid. We will use phenyl Magnesium Bromide to give the electrons to the carbon dioxide and form a salt. Then in the acidic environment, the H+ will protonate the reactants and form benzoic acid. The Benzoic acid will then be extracted with NaOH and then HCL. In this lab we refluxed ether bromobenzene and magnesium turnings in a three necked round bottom flask. The contents were then poured over dry ice and mixed with HCl. Then it was washed several times with water and a %5 NaOH solution. The ether was evaporated, and then benzoic acid was precipitated with HCl and filtered out in a Buchner funnel. The product was also analyzed using a KBr pellet in the FTIR. Our measurements and calculations found a 10.6% yield with melting points between 119.8-122.3 degrees Celsius which gives a range of 3.5 degrees Celsius. Our product had a 59.57% match with the benzoic acid in the computers library. Despite this low percent match we believe that we made a fairly pure substance because of the low melting point range and the distinct smell of benzoic acid present. Our key results show a 10.6% yield with melting points between 119.8-122.3 degrees Celsius with a range of 3.5 degrees Celsius and a 59.57% FTIR match. These results indicate that we fulfilled our experimental and educational purpose. Based on theory, the synthesis of benzoic acid was expected, and that is what our results show. The results were not different from expected. In this lab I learned how to use a three-necked flask. This lab relates to class where we are studying carboxylic acids because we synthesized a carboxylic acid. We can conclude that the lab and procedure did a good job of producing the intend product while illustrating important chemical concepts. Possible sources of error in this lab could be mistakes in draining in the separatory funnel and using too much product in the KBr pellet. Our error with the FTIR % match probably occurred because we used too much product relative to KBr. This blocked too much light in the GRIR and lowered our percent match. To remedy this issue in the future we would use less product relative to KBr.