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CHEM 301 Organic Chemistry 1 Laboratory Fall 2022 Lab 6: NBS Bromination Template LAB REPORT TEMPLATE Format: 1 inch all around; Times New Roman; font size 12; spacing 1.15; justified text. Statement at the end: This work is my own work and all help or outside sources have clearly been marked. Must be signed. All graphs, tables, figures, the general outline etc . must follow the format of The Journal of Organic Chemistry . NO header (that is: do not have the heading above “Chem 301 Organic …….”). --------------------------------------------------------------------------------------------------------------------- Please keep this table here at the top (but not this prompt) 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: Summarize the experiment here; include a graphic that represents the experiment: you could overlay the structure of the product with a picture of your product or of the rxn flask. (Note: Total word count for this section 50-100 words: not more – not less; please include word count at the end of your abstract in parentheses.) representative image here (if from external source, please list source at the end in the reference section) 1 ■ INTRODUCTION (Note: Total word count for this section 300-320 words: not more – not less) Hydrocinnamic acid ( 3-phenylpropanoic acid ) 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 manufacturing and processing of food. Brominated Hydrocinnamic acid (3-Bromo-3-phenylpropanoic acid) Provide some background on the use of hydrocinnamic acid (as available) and on the brominated hydrocinnamic acid (find its correct IUPAC name on SciFinder) (as available). The brominated was conducted via the use of NBS and AIBN. The NBS was a reagent used as the brominating

CHEM 301 Organic Chemistry 1 Laboratory Fall 2022 Lab 6: NBS Bromination Template 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 (insert citation here ) Include the fact that this was a radical reaction. Show the reaction diagram as Scheme 1 (mention it) - similar to the one shown in the lab book: include solvent, reaction time and temperature. Give each reagent, and the products, a bolded small number underneath, starting at 1 (the solvent will not get a number). Scheme 1. ….text here (Follow JOC Format!) Show the rxn here: small about ½ -1 inch in size Include the work-up. Explain why water was used to precipitate the solution into it; include the solubility of succinimide in water (reference your source here: if an online book – please cite as book, not the URL). Mention how the product was isolated, dried and analyzed. Explain the significance/background/relationship of melting point analysis and purity of a compound. Look up the reaction in SciFinder-n, cite the article and summarize their method and yield (how it was different/same). (include your word count in parentheses at the end of the introduction section) Note: any information that you look up must be referenced and referenced as superscript numbers, like this: 1 ; no direct quotes – no rewording of original phrases; no reference to the lab book. ■ RESULTS AND DISCUSSION Yield and Appearance The solid had an off white and yellow color. The solid had an appearance that looked similar to spheres and powder . The reaction produced 2.720 g (85 % yield) of Brominated Hydrocinamic Acid was recovered from the reaction and .007g were produced after sublimation. The reaction produced …….g (…..% yield) of brominated hydrocinnamic acid (base it on the limiting reagent: either NBS or hydrocinnamic acid). Include the atom economy and reaction efficiency. (How to calculate all this is explained in lab 1 material in the lab book/pdf file). Melting Point 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. Based on your results, answer the following questions and explain ( e.g. why or why not; Note: when answering the questions below, please do not repeat them, nor include (1) or (2)). (1) How pure is your product based on its m.p. range and compared with the literature value? (Explain) The product is impure, this is seen because it has a melting point range (128 – 131.3 °C) compared to the literature value (135 – 138 °C) has a difference greater than 2 °C.

CHEM 301 Organic Chemistry 1 Laboratory Fall 2022 Lab 6: NBS Bromination Template (2) How does your reaction compare with the reaction listed on SciFinder-n? (a) regarding yield (b) regarding atom economy and reaction efficiency (c) which of the two (yours or theirs) was more successful? (Explain) ■ EXPERIMENTAL SECTION (Note: the experimental section does not discuss or explain things!) 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 provided by Instructor. Acetic acid (glacius) was produced Alfa Aesar and had a purity of 99%. A Hot Water bath was used and heated to 85 °C over a 45-minute time period. Melting point apparatus (make, model), IUPAC name of your compound in italics here : Briefly describe your synthesis; include actual amounts (moles in paratheses), solubilities, temperatures, appearances, times, how isolated, filtered? Washed? Dried? How long dried? Note: any information that you look up must be referenced and referenced as superscript numbers, like this: 1 ■ CONCLUSION Comment briefly about how successful your reaction was based on yield and purity? ■ REFERENCES Any time you look up information that you do not know, you must include the source in this section. (Please make sure the format is correct; if in doubt, check some of the JOC journals ); for websites, include the URL and when accessed; for books and patents: see JOC; for articles, see below; do not use the LU lab manual as a reference. Please reference at least one peer-reviewed article, one book, and one on-line resource. (1) Lilley, T.H.; Linsdell, H.; Maestre, A. Title of your Article. J. Chem Soc., Faraday Trans. 1992 , 88 , 2865-2872. Books: Title ; Last name, Initial. Initial. Ed or Eds (for more than one editor); name of publishing company: city of publishing company, year of publication.

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CHEM 301 Organic Chemistry 1 Laboratory Fall 2022 Lab 6: NBS Bromination Template (1) Enantioselective Organocatalysis Reactions and Experimental Procedure ; Dalko, P. I., Ed; Wiley-VCH: Weinheim, 2007. (2) Asymmetric Catalysis ; Brooks, J.; Meyer, F., Eds; Wiley-VCH: New York, 2009. Websites : (1) URL title and address (accessed …… date ) Statement at the end: (remove all words in yellow): This work is my own work and all help or outside sources have clearly been marked. Must be signed.