Draw the product that will be obtained from the reaction of each of the following alcohols with HOCl. The condenser was not necessary in the final distillation because the boiling point of 2. My main interests at this time include reading, walking, and learning how to do everything faster. Psst: If you find my website helpful or enjoyable, please join my newsletter and/or send me an emailI want to hear from you! This nature of the reaction allows to hydrolyze esters back into a carboxylic acid and . Draw the organic product of the following nucleophilic substitution reaction. 0000008133 00000 n <<3baea9eb20b21f4494ce8fadbea0b8fb>]>> trailer <<5C1A0695A6EB4876B809F5465F0BE5CB>]/Prev 108627>> startxref 0 %%EOF 40 0 obj <>stream collected in Erlenmeyer flask, The distillate collected has some white HWKs0WgE$D%Cpszpu; !Nfo} @hqW8A!LtgWm]QH` *qA`oVpDd@5a8*At[} ~.T? Draw the major organic product formed when the compound shown below undergoes a reaction with CH_3OH in the presence of HCI. xb```f````c`ef`@ ;FE F7&&u'9UP_@XS`zB9jvYKx7{X0HmRz|%zXeWELa47t*rMK88o]#J2AD3HZsw5:f&2yk}e"vmuzMR^wY$ However, they are corrosive chemicals and give the moderate yield of methylesters. The purpose of this lab is to synthesize benzocaine, an ester, from p-aminobenzoic acid, a carboxylic acid, by Fischer Esterification. Step-by-Step Mechanism of Fischer Esterification Draw the reaction that would occur if you added aqueous HCL to a diethyl ether solution containing benzoic acid and piperazine. 0000006684 00000 n Essentially, we are drawing the reverse order of Fischer esterification so, in the first step the ester is protonated promoting the nucleophilic attack of water: Notice that just like the Fischer esterification, the process is an equilibrium which makes the reaction a little challenging as it may require higher temperatures and removal of the alcohol as it is formed to push the equilibrium forward. Draw the product and mechanism for the esterification reaction of acetic anhydride and 1-octanol. Acid-catalyzed carboxylic acid esterification and ester hydrolysis mechanism: acylium ion as a sharing active intermediate via a spontaneous trimolecular reaction based on density functional theory calculation and supported by electrospray ionization-mass spectrometry. Draw the organic intermediate of this reaction. 0000007524 00000 n and How would you classify the product of the reaction? 20.21 (a) This synthesis requires the addition of one carbon. 190 47 product while shaking and releasing pressure during separation. In a 30-cm. We have seen that all the steps in the Fischer esterification are reversible and the equilibrium is shifted toward the ester product by using an excess of alcohol. Need some good practice on the reactions of carboxylic acids and their derivatives? Similarly, they can not form a stable carbocation and do not undergo an elimination reaction. 0000002373 00000 n obtained, After second time an oily mixture was l_2.K {H endstream endobj 25 0 obj <> endobj 26 0 obj <>stream Ru-Sn/Al2O3 is a chemoselective catalyst for hydrogenation of -COOH group of benzoic acid. reactants was chosen because from the mechanism we can see that in the starting material : an American History (Eric Foner), Fischer esterification of benzoic acid lab report. Draw the product of the following reaction between a ketone and an alcohol. 0000011949 00000 n remove the ether, Once the t-butyl is distilled off, then butyl methyl ether and decant again, Perform a simple distillation to The Chemistry of Carboxylic Acids - University of Colorado Boulder Benzoic Acid from the Oxidation of Toluene | Hobby Chemistry Cross), Brunner and Suddarth's Textbook of Medical-Surgical Nursing (Janice L. Hinkle; Kerry H. Cheever), Biological Science (Freeman Scott; Quillin Kim; Allison Lizabeth), Chemistry: The Central Science (Theodore E. Brown; H. Eugene H LeMay; Bruce E. Bursten; Catherine Murphy; Patrick Woodward), Give Me Liberty! We take an ester containing 18O isotope in the alkoxy part and react it with a hydroxide. Draw the product(s) of reaction of the compound below: Ester Hydrolysis and Saponification Preferences: [{Image src='product3275076359212539097.jpg' alt='product' caption=''}]. The Fischer exterification technique is utilized in the academic and industrial settings due to the simplified synthesis and safety parameters of the overall reaction. 192 0 obj<>stream Lets see how that happens by drawing the complete mechanism of the reaction: After the addition of the OH and elimination of the OR, a carboxylic acid is formed. PDF Lab5: Preparation of Methyl Benzoate form an ester. 6.1 g of benzoic acid and 20 mL of methanol, and 2 mL of concentrated sulfuric acid. Learn about esterification and its mechanism. Answer the following questions about this reaction. And it quickly reacts with the OH or OR strong bases transforming into a carboxylate ion which is less electrophilic than carboxylic acids and cannot be attacked by the RO alkoxide anymore. Ph3P-I2 mediated aryl esterification with a mechanistic insight The purity of the benzoate will then be determined using infrared spectroscopy. Draw the major product of this reaction of this alkene with HBr. Draw the organic product formed in the given reaction. The p roduct of the first experiment in which methanol separatory funnel with 50ml of water, Rinse flask with 35ml of t-butyl An efficient general method for esterification of aromatic carboxylic To evaluate the effect of the substrate's acidity on the reaction, a series of carboxylic acids (1) were reacted with 3-nitrophenol to provide 3-nitrophenolic esters 2.As shown in Table 2, the reaction using benzoic acid and its derivatives proceeded smoothly to provide the esters 2 in good to excellent yields regardless of their pK a values. View the full answer Step 2/4 Step 3/4 Step 4/4 Final answer Transcribed image text: There is 7 H at the left-hand-side and 6 H at th right hand side. 1. Draw the major organic product. Draw the aldol reaction mechanism between 4-methylbenzaldehyde and acetophenone. 110. liquids, Acute 0000005182 00000 n The experimental procedure was followed pretty much as written. Draw the structure of the major organic product formed in the reaction. Recent Advances in the Synthesis of Carboxylic Acid Esters This page titled 15.7: Preparation of Esters is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by Anonymous via source content that was edited to the style and standards of the LibreTexts platform; a detailed edit history is available upon request. B. 1 mol of benzoic acid was used in this reaction and 1 mol of methanol. Based on the following chemical equation, how many moles of citric acid Why is the sulfuric acid necessary? Below is the reaction between benzoic acid, a carboxylic acid, and ethanol, an alcohol. Weight of distilled methyl benzoate: 6.274 g, (Weight of distilled methyl benzoate) / (Weight of benzoic acid) * 100 = Percent recovery. Steric hindrance at the ortho position of the . Kek Final Paper - SlideShare Esterification of benzoic acid (mechanism) 7. And this is when the base-catalyzed ester hydrolysis turns to be more beneficial. 0000000836 00000 n 0000009123 00000 n Draw the major organic product for the following reaction. Esterification: Mechanism, Properties and Uses - Collegedunia Draw the organic product of the nucleophilic substitution reaction. 356 0 obj <>stream Accessibility StatementFor more information contact us [email protected] check out our status page at https://status.libretexts.org. Draw the product of the organic reaction below. Azeotropic distillation is the process of separation of liquids mixture on the basis of volatilities. This reaction involves an initial protonation of the carboxyl group, an attack by a nucleophilic Continue Reading Check Writing Quality Good Essays Learn. Tin(II) and titanium(IV) show similar kinetic dependencies, although the order of the reaction varies with the acid that is being Draw the organic product(s) of the reaction of phenylacetaldehyde with 2 CH3OH, HCl catalyst. The mechanisms of the Fisher esterification reaction is an equilibrium process that takes place over a few hours of refluxing. Draw the product and a complete mechanism for its formation, for the Fischer esterification of benzoic acid. (If no reaction occurs, draw the starting material.) The new method overcomes the well-known drawbacks of the chemical route in favor of a more sustainable reaction process. 15.7: Preparation of Esters - Chemistry LibreTexts 'YFNFge-e6av jI { Acid_Anhydrides_react_with_alcohols_to_form_esters : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Acid_Anhydrides_React_with_Amines_to_Form_Amides : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Acid_Anhydrides_react_with_water_to_form_carboxylic_acids : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", General_Mechanism_of_Anhydride_Reactions : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Reactions_of_Acid_Anhydrides_with_Nitrogen_Compounds : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Reactions_of_Acid_Anhydrides_with_Oxygen_Compounds : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, { Nomenclature_of_Anhydrides : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Properties_of_Anhydrides : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Reactivity_of_Anhydrides : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Synthesis_of_Anhydrides : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, [ "article:topic", "showtoc:no", "license:ccbyncsa", "licenseversion:40" ], https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FOrganic_Chemistry%2FSupplemental_Modules_(Organic_Chemistry)%2FAnhydrides%2FReactivity_of_Anhydrides%2FAcid_Anhydrides_react_with_alcohols_to_form_esters, \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}\) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\), Acid Anhydrides React with Amines to Form Amides, status page at https://status.libretexts.org. While separating the layers, it gauge when to close the stopcock perfectly, so that led to a loss of eventual product. The possibility of recycling these metallic benzoates was also demonstrated . Because the presence of water molecules or moisture tends to shift the reaction in a backward direction and decrease the yield. 0000012873 00000 n How can we increase the yield of the product? v`g sh'[m e H0S4"}A49d9U2R2XhL2"%2 ak>-sRHn1FsIJC*)3(ur~+A)71^EtTw!ym('dCrI Esterification. 3) Leaving group removal. mixture. We have a primary carbon and the acetate is not the worst leaving group certainly better than the ethoxide. Ester Hydrolysis: Acid and Base-Catalyzed Mechanism. draw the organic product formed in the following reaction. Solved 1) In each of the following reactions (i) using | Chegg.com In the laboratory manual, they state that the Esterification - University of Illinois Urbana-Champaign To identify and describe the substances from which most esters are prepared. Fischer Esterification of Benzoic Acid & Methanol in HCl (RXN Mechanism) - YouTube This video screencast was created with Doceri on an iPad. Copyright 2023 StudeerSnel B.V., Keizersgracht 424, 1016 GC Amsterdam, KVK: 56829787, BTW: NL852321363B01, Principles of Environmental Science (William P. Cunningham; Mary Ann Cunningham), Educational Research: Competencies for Analysis and Applications (Gay L. R.; Mills Geoffrey E.; Airasian Peter W.), Forecasting, Time Series, and Regression (Richard T. O'Connell; Anne B. Koehler), The Methodology of the Social Sciences (Max Weber), Psychology (David G. Myers; C. Nathan DeWall), Campbell Biology (Jane B. Reece; Lisa A. Urry; Michael L. Cain; Steven A. Wasserman; Peter V. Minorsky), Civilization and its Discontents (Sigmund Freud), Business Law: Text and Cases (Kenneth W. 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Draw a stepwise mechanism for the following organic reaction: draw the organic product of the following reaction. Such a reaction yields an ester that contains a free (unreacted) carboxyl group at one end and a free alcohol group at the other end. looks clear, As the cooled reaction mixture was Fischer esterification of benzoic acid-1 - Fischer esterification of benzoic acid Purpose: The goal - Studocu Fischer esterification of benzoic acid lab report fischer esterification of benzoic acid purpose: the goal of this experiment is to use reaction called fischer Skip to document Ask an Expert Sign inRegister Sign inRegister Home Esters are usually pleasant-smelling compounds characterized by an alkoxy group bonded to a carbonyl carbon. Organic Syntheses Procedure Video transcript. A. 110 217 Theoretical yield: 11 Further, water must be removed as it is produced to shift the equilibrium towards ester formation, to increase the yield. At the carbonyl carbon, esters react with nucleophiles. 0000004003 00000 n 3 Mich 2020 (Relevant Mrkt), Comp Law Rd. PDF Identification of Kinetics of Direct Esterification Reactions - CHERIC Draw the product and a complete mechanism for its formation, for the Abu Bakar Salleh (Organic Solvent): Estadsticas de influencia Niger Hydrogenation of benzoic acid using mono- and bimetallic catalyst of Ru, Pd, Co, and Re yielded different products. Checked by C. S. Marvel and Tse-Tsing Chu. Abu Bakar Salleh works at Enzyme and Microbial Technology (EMTech) Research and is well known for Organic Solvent, Organic Solvents and Thermostable Lipase. The hydrogen ion (H+) of alcohol is removed from the alcohol whereas hydroxide (OH) is removed from the acid to form water molecules. KFjqffrO:Vxkx>~fgt(7|8xrD]! 0000010606 00000 n Lets start with the mechanism of acid-catalyzed hydrolysis of esters. Draw the mechanism for the reaction between 1-butene and HBr. The reaction often involves an alcohol and a Bronsted acid (such as a carboxylic acid, sulfuric acid, or phosphoric acid ). At equilibrium, the reaction mixture has appreciable quantities of products and reactants. Show stereochemistry where appropriate. [{Image src='reaction8479124686314675931.jpg' alt='reaction' caption=''}], Draw a stepwise mechanism for the following reaction: CH_3 CH_2 OH. In this Fischer esterification reaction, benzoic acid (a carboxylic acid) is esterified with methanol (an alcohol) in the presence of sulfuric acid (an acid catalyst) to produce methyl benzoate (an ester). A) 3-pentanol B)1-pentanol C)2-methyl-2-pe, Draw the organic product of the following nucleophilic substitution reaction. If the reaction produces a racemic mixture, draw both stereoisomers. 0000012103 00000 n The most common example of acid catalyst fisher esterification is as follows: The mechanism of Fischer esterification is similar to acid-catalyzed reactions. If a solution of methyl alcohol and benzoic acid containing a small amount of sulfuric acid is headed under reflux for about an hour the ester methyl benzoate is formed. oi|oe%KcwX4 n! Esterification Limits of Benzoic and Toluic Acids with Lower Alcohols Rate and Equilibrium of Esterification of 2-butanol and 2-propanol by Sulfuric Acid The Application of Victor Meyer's Esterification Law to Neighboring-xylic Acid and Its Reduced The LibreTexts libraries arePowered by NICE CXone Expertand are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. b) Washing the organic layer with saturated sodium chloride solution makes the water HWMo8Wh 8"hQT=${pn,9J"! This was proved by the isotope labeling experiment where methanol has an oxygen isotope (O18) treated with benzoic acid. Benzoic Acid from Ethyl. Advances in the Modification of Starch via Esterification for Enhanced 0000009431 00000 n separatory funnel, Pour the bicarbonate layer into an Draw the structure of the alkylbromide and the nucleophile that will react in an SN2 reaction given the product shown. Draw all stereoisomers formed in the given reaction. The most important polyester, polyethylene terephthalate (PET), is made from terephthalic acid and ethylene glycol monomers: Polyester molecules make excellent fibers and are used in many fabrics. 0000003924 00000 n HWn8+RHJen1E;QM"$]%)JQh> ?4@9)/P''`V/`wp-:3R#\l@g k trailer This means the actual starting amount was slightly lower than measured. 0000047618 00000 n Concentrated sulfuric acid is added as a catalyst in the esterification procedure, even though another acid (benzoic acid) is one of the organic reagents used. 0000010044 00000 n acid. (Methyl Benzoate + Water) - YouTube A carboxylic acid (like benzoic acid) and an alcohol (like methanol) will form an equilibrium with an ester (in this case, methyl benzoate) and water.. So if you start with the carboxylic acid, and you add an alcohol, and a source of protons, you're gonna form your ester, and you're also going to make water in this process. Lab 8 - Fischer Esterification - Lab #8 Fischer Esterification Monday This gave me a percent yield of 18%. My stating material was 10 of benzoic acid and at the end I had 2 of methyl Draw the major product formed in the following reaction with NaCN and other reactants ethanol and water. Carbonyl is a weakly electrophilic compound that is attacked by strong nucleophiles. Then, it was connected to a condenser and placed in an oil-bath that was preheated at 170C. Once benzoic acid is added to one end of the ethylene glycol, the remaining OH group is more active toward esterification. It is obtained from the bark of the white willow and wintergreen leaves. Flow chart for the isolation of methyl . 3. Draw the products of benzoic acid reacting with sodium hydroxide. 11. The process of esterification has been reported to greatly improve the hydrophobic property of starch by substituting the hydroxyl groups on each glucose residue thereby converting it to a hydrophobic ester group with reagents (organic and inorganic acids, and their derivatives). added to the water it began turning 0000004248 00000 n The separatory funnel must be frequently inverted, and the stopcock must be opened Draw the products of the following reactions. Typical procedure for the esterification with DMC A flask (10 mL volume) was filled with benzoic acid (366 mg, 3.0 mmol), DMC (540 mg, 6.0 mmol), K 2 CO 3 (41 mg, 0.3 mmol), and TBACl (205 mg, 0.9 mmol). Draw the reaction between benzoic acid and NaOH and explain why it is necessary to use 3 M NaOH as the aqueous layer to better separate the benzoic acid. of the round-bottom flask, Set up a reflux condenser and add a PDF MECHANISM (Fischer esterification) - Texas Christian University Draw the ester that is formed from the reaction of benzoic acid and ethanol. For HCrO, Ka is very large and Ka is 3.10 x 10-. A Study of the Esterification of Benzoic Acid with Methyl Alcohol Using shaking, some bubbling is seen, When 15ml NaCl is added & shook, before you go on to the esterification experiment. Become Premium to read the whole document. Check this 45-question, Multiple-Choice Quiz with a 50-min Video Solution covering the reactions of acids, esters, lactones, amides, acid chlorides and etc. This is a common mechanism in organic chemistry, and its mastery is important in learning how carbonyl compounds behave. (CH_3)_3 C CO_2 CH_3. Alcohol is used in large excess to remove water molecules by azeotropic distillation. startxref ether solution remaining in the Assume the reaction has been terminated and neutralized. Acid Anhydrides react with alcohols to form esters is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts. )Z)<>y3+ ?cJaYdf~?TXb%bFsd_0&0ckxH?a{G6b"fdi@Oc@sX hV|xCF + 0WLq 15: Organic Acids and Bases and Some of Their Derivatives, Basics of General, Organic, and Biological Chemistry (Ball et al. Carboxylic Acids and Their Derivatives. A. precipitate. PDF Fischer Esterification of 3-ntrobenzoic acid 2017 - Truman State University Draw a detailed mechanism for the aldol condensation reaction of Benzaldehyde and 4' methoxyacetophenone in KOH and 95 percentage ethanol. 0000057501 00000 n A: Click to see the answer. The method is equally convenient for esterification of a dicarboxylic acid 4, its anhydride, and chloro, iodo and nitro substituted aromatic carboxylic acids. Turn in the product into the labeled container. Salicylic acid is a monohydroxybenzoic acid that is benzoic acid with a hydroxy group at the ortho position. Legal. was added it formed 4 different layers, 50ml of the aqueous layer were Now, if the reaction was SN2, then the 18O oxygen should still appear in the carboxylate ion: However, experimental studies have indicated that the reaction goes by addition-elimination mechanism as the oxygen in the carboxylate comes from the hydroxide ion: The isotope labeling and other studies confirming the addition-elimination path wouldnt be complete if we didnt find one exception, right? 54 Esterification of Substituted Benzoic Acid acids,7,8 ionic liquids,9,10 11,12or solid acid catalysts. Draw the ester that is formed from the reaction of benzoic acid and The reaction mechanism for the most active titanium aminotriphenolate complex 10 was further examined with DFT-D3 calculations at the BP86/TZ2P level of theory . What happen when ethanol reacts with benzoic acid? - Quora Draw the acetal produced when ethanol adds to ethanal. This experiment was conducted to synthesize methyl benzoate form benzoic acid and methanol by using the Fischer esterification method. Benzoic Acid + Methanol = ?? (Methyl Benzoate + Water) - YouTube Understand the esterification definition and ester general formula, and also see the example of the esterification reaction of fatty acids. However, the mechanism is a little different. The acid catalyzed esterification of benzoic acid w ith methanol can be represented as in Figure 3. After the protonation of the carbonyl, instead of the nucleophilic addition to the carbonyl, we have a loss of a leaving group by an SN1 mechanism: This C-O bond cleavage occurs because it produces a relatively stable tertiary alkyl group just like we have seen in the SN1 mechanism. 2 - Mich 2020 (Intro Comp Policy), Instructions for Reading Week - Comp Policy, Trinity College Dublin University of Dublin, Introduction to Operations Management (BU2560), Foundations of Medicine 1 - Introductory Human Biology (FM1010), Neurology in Health & Disease (MDSA30220), Political Economy & Social Justice (SSJ20150), Qualitative Methods for Sociological Research (SO4037), International Financial Reporting II (AY325), Fungal and Bacterial Secondary Metabolism (Bi441), International Arbitrage & Interest Rate Parity, Free Movement of Goods (Art.34 TFEU) Sample Essay, Const Site Management - Lecture notes 1-12, Lab 10 & 11 - Parallel RLC Band Pass Filter, EOC Q&A L2 - Sample questions and answers related to week 2 material, FM exam 2021 - facilities management exam questions and answers, 2.