2. Lets consider a specific example of an ester with methyl or primary alkyl derivative: Can this SN2 reaction be a suitable alternative to the addition-elimination mechanism we discussed above? soln into round-botttom flask, Wash drying agent with 3 to 5 ml of t- Erlenmeyer flask, Dry ether soln over anhydrous calcium 61e` endstream endobj 23 0 obj <>stream Organic Chemistry 1 and 2Summary SheetsAce your Exam. Ru-Sn/Al2O3 is a chemoselective catalyst for hydrogenation of -COOH group of benzoic acid. identify conversion of acid end groups, degree of polymerization and the concentration of by-products rates according to the change of operating conditions. That is the reason, dried primary alcohols are preferably used in Fischer esterification. Draw a structure for the major organic product you would expect from reaction of 3-methyl-3-pentanol with HCl. The goal of this experiment was reached because the Fischer esterification reaction was used to Draw all stereoisomers formed in the given reaction. 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 . This labeled oxygen atom was found in the ester. 3. 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. Draw a reaction mechanism for the electrophilic aromatic substitution of benzoic acid to produce m-nitrobenzoic acid? Steric hindrance at the ortho position of the . krCsS ' xweUI*Y{WsT%%U#9>0>PUb5*+n" zb"e([J'}b. Weight of distilled methyl benzoate: 6.274 g, (Weight of distilled methyl benzoate) / (Weight of benzoic acid) * 100 = Percent recovery. So, does the ethoxide attack the carbonyl carbon or the CH2 of the ethyl group? 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. Clarkson; Roger LeRoy Miller; Frank B. However, it can be simplified by the overall equation: C 7 H 8 (l) +2 KMnO 4 (aq) -> KC 7 H 5 O 2 (aq) + 2 MnO 2 (s) + KOH (aq) + H 2 O (l) Draw out the major organic product formed in the following reaction. Recently . 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. The round bottom flask was placed on a heating plate and was refluxed starting at 109 C. Introduction to Psychological Research and Ethics (PSY-260), Instructional Planning and Assessments for Elementary Teacher Candidates (ELM-210), Nursing Process IV: Medical-Surgical Nursing (NUR 411), Managing Projects And Programs (BUS 5611), Introduction To Computer And Information Security (ITO 310), Nurs & Healthcare I: Foundations [Lec] (NURS356), Nutrition and Exercise Physiology (NEP 1034), Foundational Concepts & Applications (NR-500), Professional Application in Service Learning I (LDR-461), Advanced Anatomy & Physiology for Health Professions (NUR 4904), Principles Of Environmental Science (ENV 100), Operating Systems 2 (proctored course) (CS 3307), Comparative Programming Languages (CS 4402), Business Core Capstone: An Integrated Application (D083), Chapter 15 Anxiety and Obsessive-Compulsive Disorders, Database Systems Design Implementation and Management 9th Edition Coronel Solution Manual, Summary Intimate Relationships - chapters 1, 3-6, 8-11, 13, 14, Active Learning Template Nursing Skill form Therapeutic Communication, Wong s Essentials of Pediatric Nursing 11th Edition Hockenberry Rodgers Wilson Test Bank, EDUC 327 The Teacher and The School Curriculum Document, 1.1 Functions and Continuity full solutions. 0000064940 00000 n Draw the structure for an alkene that gives the following reaction product. All rights reserved. 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. 0000015725 00000 n Why is the sulfuric acid necessary? This was proved by the isotope labeling experiment where methanol has an oxygen isotope (O18) treated with benzoic acid. v`g sh'[m e H0S4"}A49d9U2R2XhL2"%2 ak>-sRHn1FsIJC*)3(ur~+A)71^EtTw!ym('dCrI and opening the stopcock often. 0000008133 00000 n 1. The methyl benzoate can be synthesized by esterification of benzoic acid with methanol using sulfuric acid as a catalyst. 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. )Z)<>y3+ ?cJaYdf~?TXb%bFsd_0&0ckxH?a{G6b"fdi@Oc@sX hV|xCF + 0WLq However, they are corrosive chemicals and give the moderate yield of methylesters. Esters are made by the reaction of a carboxylic acid with an alcohol, a process that is called esterification. 3. [{Image src='reaction8479124686314675931.jpg' alt='reaction' caption=''}], Draw a stepwise mechanism for the following reaction: CH_3 CH_2 OH. typical yield for students is around 7g. top layer looks cloudy, After pouring organic layer into RBF, 0000005749 00000 n Ester Hydrolysis: Acid and Base-Catalyzed Mechanism. please draw the reaction mechanisms: 2-chloro-2-methylpropane + AgNO3 in ethanol Bromocyclohexane + AgNO3 in ethanol. Answer the following questions about this reaction. Disclosure: As an Amazon Associate I earn from qualifying purchases. Checked by C. S. Marvel and Tse-Tsing Chu. 0000009890 00000 n a cloudy white solid, Methyl benzoate is what is being Procedure for esterification of benzoic acid and heptanol. This nature of the reaction allows to hydrolyze esters back into a carboxylic acid and . separatory funnel, Pour the bicarbonate layer into an 2) Deprotonation by pyridine. Draw the organic product formed in the given reaction. This experiment was conducted to synthesize methyl benzoate form benzoic acid and methanol by using the Fischer esterification method. Some esters can be prepared by esterification, a reaction in which a carboxylic acid and an alcohol, heated in the presence of a mineral acid catalyst, form an ester and water: The reaction is reversible. Draw the major organic product for the following reaction: 1-bromo-2-methylcyclohexane with reagent H 2 O / isopropyl alcohol. As steric crowding slows down the rate of reaction,primary alcohols are mostly used for this reaction. %PDF-1.6 % product while shaking and releasing pressure during separation. Draw the major organic product formed by the reaction of 2-hexyne with the following reagent: H_2O in H_2SO_4/HgSO_4. Why we can not use tertiary alcohols for Fischer esterification? Note that methanol becomes part of the reaction product. Legal. There is 7 H at the left-hand-side and 6 H at th right hand side. Draw the product that is formed when 4-methyl-1-pentene reacts with methanol in the presence of an H2SO4 catalyst. A) 3-pentanol B)1-pentanol C)2-methyl-2-pe, Draw the organic product of the following nucleophilic substitution reaction. A commercially important esterification reaction is condensation polymerization, in which a reaction occurs between a dicarboxylic acid and a dihydric alcohol (diol), with the elimination of water. copyright 2003-2023 Homework.Study.com. Become a Study.com member to unlock this answer! It has a role as an antiinfective agent, an antifungal agent, a keratolytic drug, an EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor, a plant metabolite, an algal metabolite and a plant hormone. Draw the product and mechanism for the esterification reaction of acetic anhydride and 1-octanol. Tertiary alcohols can not be used for Fischer esterification because they may lead to carbocation formation and give an elimination reaction. }mtH1& pdf, Chapter 01 - Fundamentals of Nursing 9th edition - test bank, Is sammy alive - in class assignment worth points, 1-1 Discussion Being Active in Your Development, Carbon Cycle Simulation and Exploration Virtual Gizmos - 3208158, QSO 321 1-3: Triple Bottom Line Industry Comparison, Leadership class , week 3 executive summary, I am doing my essay on the Ted Talk titaled How One Photo Captured a Humanitie Crisis https, School-Plan - School Plan of San Juan Integrated School, SEC-502-RS-Dispositions Self-Assessment Survey T3 (1), Techniques DE Separation ET Analyse EN Biochimi 1, After 45 min the benzoic acid melted A. MODELING OF THE ESTERIFICATION REACTOR In the modeling of a direct esterification reactor, we first assumed that polymerization reactions involved can be regarded as reactions added to the water it began turning Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. because a lot of pressure is produced in the reaction, and it must be released by inverting Use between 1 and 2 g of it! 0000011795 00000 n 3. Solved 7 Esterification A Give The Mechanism Chegg The Mechanism of the Alkaline Hydrolysis of Methyl April 10th, 2018 - The Mechanism of the Alkaline Hydrolysis of Methyl 2 The . Elimination (1,2-elimination) is an extremely important reaction mechanism of the carbonyl (C=O) group, which is present in such functional groups as aldehydes, ketones, carboxylic acids and carboxylic acid derivatives. <<3baea9eb20b21f4494ce8fadbea0b8fb>]>> &.K{)Uxq6{pK,>A80V{xqb$l1[y-c99tdDIJJ>y>Y E IU0'X6E7ewWwPC^n`p7COV0zXc}`)D9cCi37APNOG-H)BNbX\,$evu^h>?n5J++[WV[kO77;5)%]d ;+ Benzoic Acid with Cl_2, FeCl_3. Preparation of Methyl Benzoate Academia edu. To summarize, yes, the nucleophilic addition-elimination mechanism predominates in ester hydrolysis, however, you should not exclude the possibility of SN2 and SN1 reactions depending on the structure of the ester. The new method overcomes the well-known drawbacks of the chemical route in favor of a more sustainable reaction process. Determine the weight of the dry benzoic acid and calculate the theoretical yield of methyl benzoate based on the weight of benzoic acid with which you started (6.1 g) less the weight of benzoic acid recovered. Therefore, special methods are being used for the synthesis of esters by using tertiary alcohols. Salicylic acid is a monohydroxybenzoic acid that is benzoic acid with a hydroxy group at the ortho position. !^\c5}]Fy!H- Different factors could have contributed to this. How can we monitor the progress of a chemical reaction? 0000001060 00000 n Draw the organic product(s) formed in the given reaction. )%2F15%253A_Organic_Acids_and_Bases_and_Some_of_Their_Derivatives%2F15.07%253A_Preparation_of_Esters, \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}\) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\), source@https://2012books.lardbucket.org/books/introduction-to-chemistry-general-organic-and-biological, status page at https://status.libretexts.org. aquatic hazard, Calculations: %PDF-1.3 % BENZILIC ACID. Draw the organic product of the nucleophilic substitution reaction. 0000002210 00000 n sodium bicarbonate soln, wash the 0000002373 00000 n 0000004248 00000 n The complete mechanism showing all intermediates and arrows to demonstrate electron movement. Draw the organic product for the reaction: CH_3CH_2CH_2OH + K_2Cr_2O_7 (aq) overset{H_2SO_4}{rightarrow}. Draw the organic product formed in the below reaction. View Lab Report - Lab 8 - Fischer Esterification from CHM 2123 at University of Ottawa. 0000004003 00000 n 4. Draw the product of the following reaction. Figure 1: Fischer Esterification Mechanism of the Formation of Benzocaine 2. Exp6 prepmethylbenzoate chem234 University Of Illinois. 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). Predict the product of the reaction of p-methyl benzoic acid with each of the following: CH_3MgBr in ether, then H_3O^+. A: Click to see the answer. Strong inorganic base or acid, such as KOH (26)orH 2SO 4 (33), was also able to catalyze the esterification with DMC. Q: A 1.20 L weather balloon on the ground has a temperature of 25.0 C and is at atmospheric pressure. 772C Theoretical yield: 11 In a 30-cm. 0000002860 00000 n Starting amount of benzoic acid: 10 toxicity, Short We have developed Eudragit S-100 (ES) coated folic acid (FA) conjugated gliadin (Gd) delivery . term (acute) If more of a compound is added to one side, then equilibrium will shift towards the other side. -%2*2nTc` |!RtWQa{}>uk/aq3$qVjS9Pk9QEVb]il39yFk&64:qB4y1U^C*d 0000003466 00000 n and How would you classify the product of the reaction? Carbonyl is a weakly electrophilic compound that is attacked by strong nucleophiles. 0000005512 00000 n methylation. Step 2: Preparation of ethyl p-aminobenzoate (esterification of p-aminobenzoic acid) Place 80 ml of absolute ethanol in a 250 ml two-necked flask equipped with a double surface reflux condenser and a gas inlet tube. oi|oe%KcwX4 n! HWKs0WgE$D%Cpszpu; !Nfo} @hqW8A!LtgWm]QH` *qA`oVpDd@5a8*At[} ~.T? Further, water must be removed as it is produced to shift the equilibrium towards ester formation, to increase the yield. Can anyone show me how to draw this? 10 benzoic acid/122/mol = 0 mol actual yield: 2, Percent yield: (Actual/ theoretical) x 100= (2.07g/11)100=18%. Remember, soap is a salt of a fatty acid and can be formed when a fat (an ester derived from a glycerol and three molecules of fatty acid) is hydrolyzed by base catalysis: How do we know this is the correct mechanism of base-catalyzed ester hydrolysis? This molar ratio of 20.20 (b) 1,4-Benzenedicarboxylic acid (terephthalic acid) is a compound with the formula C8H 6O 4that gives the indicated diol on treatment with LiAlH4followed by protonolysis. Draw the major organic product formed in the following reaction. Why is alcohol used in excess in this reaction? Similarly, they can not form a stable carbocation and do not undergo an elimination reaction. %PDF-1.4 % 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. Flow chart for the isolation of methyl . 2.Fisher esterification reaction: acid-catalyzed reaction of carboxylic acids with 1 or 2 alcohols to give esters Reagents: ROH (usually solvent), HCl (strong acid) C C O OH HOH . HWn8+RHJen1E;QM"$]%)JQh> ?4@9)/P''`V/`wp-:3R#\l@g k The esterification is a reaction between an alcohol and a carboxylic acid or a carboxylic acid derivative, water and ester will be formed as products in this process under reflux. 0000010606 00000 n Draw the E1 alkene product(s) of this reaction. the smell is very strong, After pouring residue into jar it turned This is called tautomerism. 0000010183 00000 n looks clear, As the cooled reaction mixture was Essentially, we are drawing the reverse order of Fischer esterification so, in the first step the ester is protonated promoting the nucleophilic attack of water: Notice that just like the Fischer esterification, the process is an equilibrium which makes the reaction a little challenging as it may require higher temperatures and removal of the alcohol as it is formed to push the equilibrium forward. Voiceover: One way to make an ester is to use a Fischer esterification reaction. a. Butanol + NaOH/25^o C gives ? Benzoic Acid + Methanol > Methyl Benzoate + Water. The mechanisms of the Fisher esterification reaction is an equilibrium process that takes place over a few hours of refluxing. 0000003924 00000 n Video transcript. Vibration analysis was carried out to confirm TS structures and imaginary frequencies. Draw the organic product of the reaction of 1-butene with H2O, H2SO4. soluble Not a hazardous The mechanism for the reaction is quite complex. Predict and draw the products of the reaction methyllithium with ethanol. Draw the product of the organic reaction shown below. pE/$PL$"K&P Limitations of Fischer esterification are: Why is excess acetic acid used in Fischer esterification? Obtain a 10g (0.082 mol) sample of benzoic acid from the storeroom (weigh the benzoic acid to obtain an exact weight before you begin). *bV~l60mf[/;385CWd8\*l-(inVz:FRtLiVBE\?c\0CFvPeT(6".qpKi:*=J eEyn@yj),h%L;~38(=LeeT4c nr2Hi2~4K>u5[n r= 4cr0mg&XA36*jTGblW:%oe v$ wukg3pT9BH[Xh~_q9N1MI#hz11zmiI( 6TLgx;gENY^5[cU`eSM(NP},G{YI}eo;F/eSf2- ccnQ~;o{P*]3O8t0Z,jsb;L&6Kmh(u&6}X |hggvv6WN7!Ki\ Zj[[|BsRk2!pl`n?P]WMFSHog7 n5+g/dU[yp[ src='108react7399676055761647507.jpg' alt='' caption='', Draw the structure of the hemiacetal or hemiketal that results from the following reaction: butanal + isopropyl alcohol to. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. 0000057288 00000 n . Ester Hydrolysis: Acid and Base-Catalyzed Mechanism, Carboxylic Acids and Their Derivatives Practice Problems, Ester Hydrolysis by Acid and Base-Catalyzed Hydrolysis, Esters Reaction with Amines The Aminolysis Mechanism, Ester Reactions Summary and Practice Problems, Preparation of Acyl (Acid) Chlorides (ROCl), Reactions of Acid Chlorides (ROCl) with Nucleophiles, Reaction of Acyl Chlorides with Grignard and Gilman (Organocuprate) Reagents, Reduction of Acyl Chlorides by LiAlH4, NaBH4, and LiAl(OtBu)3H, Preparation and Reaction Mechanism of Carboxylic Anhydrides, Amides Hydrolysis: Acid and Base-Catalyzed Mechanism, Amide Dehydration Mechanism by SOCl2, POCl3, and P2O5, The Mechanism of Nitrile Hydrolysis To Carboxylic Acid, Nitrile Reduction Mechanism with LiAlH4 and DIBAL to Amine or Aldehyde, The Mechanism of Grignard and Organolithium Reactions with Nitriles. 54 Esterification of Substituted Benzoic Acid acids,7,8 ionic liquids,9,10 11,12or solid acid catalysts. Hence, it was proved that the O-H bond of alcohol is broken in Fischers esterification. 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). 0000009002 00000 n The reaction mixture of benzoin, prepared by the method described on p. 94, is permitted to stand until the next day, when it is filtered, washed with water but is not dried or purified. Learn. Synthetic arteries can be made from PET, polytetrafluoroethylene, and other polymers. If water was removed from the reaction mixture, it was cause equilibrium to shift towards methyl benzoate to make water and thus lead to an increased conversion of benzoic acid to methyl benzoate. collected in Erlenmeyer flask, The distillate collected has some white 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. add 2-3g of anhydrous calcium Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. Add to it 0.62 mol of methanol in a 100 mL round-bottomed flask. Draw structure for the product obtained from the reaction of beta-D-talopyranose with the reagents. ikWxF/Uw$ !hCAZopN;zi7WGf_-EW72GE1oA'Q[T)'aA`$E8i[c\22l1A}~kTqVT+?}_urV2PVfaIwT\w^uvIw^u[{6;BoS?=v;Xs$ 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. xb```f````c`ef`@ ;FE F7&&u'9UP_@XS`zB9jvYKx7{X0HmRz|%zXeWELa47t*rMK88o]#J2AD3HZsw5:f&2yk}e"vmuzMR^wY$ Draw the organic intermediate of this reaction. Hydrolysis of Esters: Mechanism and Conditions, Physical and Chemical Properties of Water, Transesterification: Mechanism and Applications, Mechanism of acid-catalyzed Fischer esterification, Electron Configuration: The Key to Chemical Reactivity, Braggs Law [n = 2d sin]: A Relationship Between (d & ), Memorizing the Periodic Table: 3 Easy & Proven Ways, Neutralization Reactions: The Acid Base Balancing. 0000002583 00000 n 0000005182 00000 n The Fischer exterification technique is utilized in the academic and industrial settings due to the simplified synthesis and safety parameters of the overall reaction. Alcohol is used in large excess to remove water molecules by azeotropic distillation. 1) Nucleophilic Attack by the Alcohol. 0000013019 00000 n Draw the major organic product for the following reaction: Draw the major organic product of the following reaction. Draw the major organic product formed when the compound shown below undergoes a reaction with NaBH4. 0000011336 00000 n %> {JMeuJ This nature of the reaction allows to hydrolyze esters back into a carboxylic acid and alcohol when the water is now used in a large excess: The reaction works even better by base catalysis (saponification) because it makes the process irreversible. 0000011949 00000 n 0000000016 00000 n 1 Furthermore, esters find extensive use within the fragrance, 2,3 flavour, 4 and functional materials industries, 5 as well as having a large . The purpose of this lab is to synthesize benzocaine, an ester, from p-aminobenzoic acid, a carboxylic acid, by Fischer Esterification. Synthesizing Methyl Benzoate from Benzoic Acid, An Art Critique on Tennis Court by Ellsworth Kelly (1949), #ART 1021 (Introduction to Art History & Appreciation II), Oxygenation and Hydrochlorination of Vaskas Complex Ir(Cl)[P(C6H5)3]2(CO), The Mental, Physical, and Social Implications of Self Enhancement, Synthesis, Determination, and Catalytic Measurement of Ruthenium Indenylidene Complexes used in Olefin Metathesis, Synthesis and Determination of [1,3,5-C6H3(CH3)3]Mo(CO)3, Synthesis and Determination of Polypyrazolylborates, Ring-Opening Metathesis PowerPoint Presentation, Double Group Transfer Reactions of an Unsaturated Tantalum Methylidene Complex with Pyridine N-Oxides.