Formal lab 2.5 Final Final

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The Conduction and Analysis of a Brominated Hydrocinnamic Acid Reaction Fall 2022 Lab 6: NBS Bromination Lab Report Item Points Out of Format 3 Title & Abstract 1 Introduction 4 Results & Discussion 8 Yield 5 Experimental 5 Conclusion 2 References 2 TOTAL 30 The Conduction and Analysis of a Brominated Hydrocinnamic Acid Reaction Tyler Hutcherson, CHEM301L, 007, 10/21/2022 Department of Biology and Chemistry, Liberty University ABSTRACT: In this experiment, a reflux apparatus was used in the process of the bromination of hydrocinnamic acid. The product is then isolated by the use of vacuum filtration. The compound was then allowed to sit for seven days. It was then analyzed for impurities by determining its melting point range. Which was revealed that it was impure. (57 words) A reflux apparatus 1 1
The Conduction and Analysis of a Brominated Hydrocinnamic Acid Reaction Fall 2022 Lab 6: NBS Bromination Lab Report INTRODUCTION Hydrocinnamic acid (3-phenylpropanoic acid) 2 is used in many different things, such as soaps, detergents, and softeners because of its sweet scent. It is also used to preserve the aroma of different frozen foods and is also added to food to help with the manufacturing and processing of food. 3 The brominated hydrocinnamic acid (3-Bromo-3-phenylpropanoic acid) 4 can be used to produce other acids. 5 The bromination was conducted via the use of NBS and AIBN. The NBS was a reagent used as the brominating agent for selective bromination and it illustrates a radical bromination reaction. The AIBN was a reagent that was used as the radical initiator for the bromination reaction. 6 This reaction is shown below in Scheme 1. Scheme 1. Bromination of hydrocinnamic acid Water is used to wash off impurities and dissolves the solute Succimide which is soluble in water at 1g per .07 ml at boiling point. 7 The product was isolated by using vacuum filtration. It was then air-dried for 10 minutes. To determine its purity its melting point range was analyzed. The range was 128 – 131.3 °C. This melting point range is lower than the literature value of the melting point range of 135 – 138 °C. This means the compound was impure. When a compound has impurities, it will melt at a lower temperature. In their research Kauffman, R.F, and Palkowitz A.D, used 12.35g in 300ml of dichloromethane and added 3.2ml of bromine dropwise to a solution of hydrocinnamic acid. The mixture was illuminated for 15 minutes then stirred for 15 minutes and concentrated. The residue was triturated with hexanes and ether and yielded 14.7g (78%). 8 The experiment which was conducted in the lab produced a yield of 85%. The reactions were similar however there were key differences. The compound was not stirred for as long and then placed on a hot water bath. Then cooled with ice-cold water and then isolated with vacuum filtration. (316 words) RESULTS AND DISCUSSION Yield and Appearance The solid had an appearance that looked similar to spheres and powder. The solid had an off- white and yellow color. The reaction produced 2.720g (85% yield) of brominated hydrocinnamic acid which was recovered from the reaction and .007g were produced after sublimation. The reaction had an atom economy of .698 and a reaction efficiency of 59.33%. Melting Point
The Conduction and Analysis of a Brominated Hydrocinnamic Acid Reaction Fall 2022 Lab 6: NBS Bromination Lab Report The melting point range of the brominated hydrocinnamic acid that was produced was 128 – 131.3 °C. The literature value of the melting point range is 135 – 138 °C. The product is impure, this is seen because it had a melting point range of 128 – 131.3 °C compared to the literature value of 135 – 138 °C has a difference greater than 2 °C. The reaction that was conducted in the lab had a yield of 85% and Kauffman, R.F, and Palkowitz A.D, had a yield of 78% . The lab experiment had an atom economy of .698 and a reaction efficiency of 59.33%. Whereas Kauffman had an atom economy .739 and a reaction efficiency of 57.6%. The lab experiment that was conducted was more successful since it had a higher yield and slightly higher reaction efficiency. EXPERIMENTAL SECTION The hydrocinnamic acid was produced by Acros Organics and had a purity of 99%. NBS was produced by Arcos Organics and had a purity of 99%. AIBN has been provided by Instructor. Acetic acid (glacial) was produced by Alfa Aesar and had a purity of 99%. A hot water bath was used and heated to 85 °C over 45 minutes. 3-Bromo-3-phenylpropanoic acid : A reflux apparatus was set up and used to brominate the hydrocinnamic acid. 3.206 grams of brominated hydrocinnamic acid (.014 moles) was synthesized by adding NBS (.014 moles) to brominate the hydrocinnamic acid (.014 moles) and then added .30 mg of AIBN (.00018 moles). The compound was stirred at room temperature for 3 minutes. It was then heated on a hot water bath for 45 minutes at approximately 85 °C. Throughout the reaction, several color changes occurred. At the beginning of the 45-minute time period, it was bright yellow, it then turned bright orange, then to a dark orange, then finally yellow and transparent. The initial temperature was 75 °C and the final temperature was 82 °C. It was then cooled for 3 minutes. An ice-cold water bath was set up and the solids were isolated using vacuum filtration. The crystals were washed with ice-cold water. The product was then allowed to dry for 10 minutes. CONCLUSION The reaction was successful with a yield of 85% however the reaction was impure. If the experiment was continued and run again with the previous product, the product would most likely be purer. Even though the impurities are present the reaction overall was a success. REFERENCES (1) Safety in academic chemistry laboratories students https://chemistry.unt.edu/sites/default/files/users/owj0001/SMALL %20ACS_safety_chemistry_laboratories_2017.pdf (Accessed 10/24/22) (2) SciFinder: 3-Phenylpropanoic acid https://scifindern.cas.org/searchDetail/substance/63569979555b613272e69c61/substance Details (Accessed 10/24/22)
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The Conduction and Analysis of a Brominated Hydrocinnamic Acid Reaction Fall 2022 Lab 6: NBS Bromination Lab Report (3 ) Metabocard for Hydrocinnamic acid: https://hmdb.ca/metabolites/HMDB0000764 (10/24/22) (4) Scifinder: 3-Bromo-3-phenylpropanoic acid https://scifinder- n.cas.org/searchDetail/substance/63569a3b555b613272e6a701/substanceDetails (Accessed 10/24/22) (5) LookChem: https://www.lookchem.com/3-Bromo-3-phenylpropionic-Acid/ (10/24/22) (6) Radical Polymerization. College of Saint Benedict/Saint John’s University. Collegeville, MN (2021, September 12). https://chem.libretexts.org/@go/page/238858 (Date Accessed 10/23/22) (7) Wiley Online Library (Succimide): https://onlinelibrary.wiley.com/doi/10.1002/047084289X.rs126 ( Accessed 10/23/2022) (8) Kauffman, R.F ., and Palkowitz, A.D, "Treatment of congestive heart failure with growth hormone secretagogues." U.S. Patent No. 6,329,342. 11 Dec. 2001. https://worldwide.espacenet.com/patent/search/family/022002400/publication/WO9908697A1? q=WO9908697A1 (Accessed 10/23/22) This work is my own work and all help or outside sources have clearly been marked