91 0 obj <> endobj Mass = (moles) x (molar mass) Goal: To reduce a ketone (4-t-butylcyclohexanone) to an alcohol using sodium borohydride, and then to verify the correct product formation via IR spectrum analysis. Vanilla is commonly used in fragrances and foods. synthesis of polymers, or in the industry for Cathiodic protection, the products formed by 7-1! Purpose Mn2+(aq)+NaBiO3(s)Bi3+(aq)+MnO4(aq), Match the item with the most closely related item accomplished what it was set out to do. alcohol to an aldehyde and ketone and the reduction of aldehyde and ketone back to an alcohol is a very common reaction in organic chemistry. : an American History (Eric Foner), Business Law: Text and Cases (Kenneth W. Clarkson; Roger LeRoy Miller; Frank B. Note! GoE$z^kPOi'6S'FlbMa Conversely LiAlH4 must always be used in aprotic solvents, such as tetrahydrofuran, and under extremely rigorous anhydrous (moisture free) conditions. Course Hero is not sponsored or endorsed by any college or university. found in vanilla and is used in artificial vanilla flavoring. Observations/Results ***Note that if there is no reaction for that lab (if we are doing a separati, should include pictures of all of the compounds used in that lab. Why not anhydrous ethanol? The hydride anion is not present during this reaction; rather, these reagents serve as a source of hydride due to the presence of a polar metal-hydrogen bond. 1) Nucleopilic attack by the hydride anion. In this reaction, the reaction is favored towards the cis end product or (kinetic 2. (0 g) / (112 g/mol) = 0 mols Write the mechanism of reduction of vanillin by sodium borohydride in water. Oxidation and Reduction Reactions in Organic. Michael Daniel Read the Experiment. CNMR. little to no filtrate. Physical Properties of Reagents: Molecular Formula C10H18O NaBH4 C 2H 6O Structural Formula Molecular W eight 154.25 g/mol 37.83 g/mol 46.07 g/mol Boiling Point 113-116C 500C 78C. One of the process routes to produce. 18.4: Reduction of Aldehydes and Ketones is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts. 3 Weldegirma, Solomon. How might the structural differences in the unknown ketone cause it to react differently than 9-fluorenone? i. i. Write the balanced equation of reaction of sodium borohydride with 4 molecules of water. Section 8.6 of Vollhardt and Schore also covers this topic. Lab 10: Reduction of Vanillin to Vanillyl Alcohol Exp. In the lithium aluminum hydride reduction water is usually added in a second step. search.ebscohost.com/login?direct=true&db=edsbl&AN=RN281558709&site=eds-live. The alcohol I used was 2-propanol. In a dram vial, dissolve 0.1 g of 9-fluorenone (part 1) or unknown aromatic ketone (part 2) in 1 mL of 95% ethanol, and cool the solution in ice (most ketones will produce a fine suspension). %PDF-1.6 % 2. Francesca Carasi-Schwartz February 6, 2019 Chem142 L13 Lab Report 1 Sodium Borohydride Reduction of Vanillin: Low Solvent Synthesis of Vanillyl Alcohol Introduction Vanillin is a renewable resource that is easily extracted from dried vanilla pods. Therefore, the sodium borohydride reduction of the ketone, 9-fluorenone was performed to yield the secondary alcohol, 9-fluorenol. similiarity to the literature values & expected peaks & absorbtions to that of 2- Addition of a hydride anion (H: -) to an aldehyde or ketone gives an alkoxide anion, which on protonation yields the corresponding alcohol. - TLC analysis: this was used to find out whether the reaction has gone to completion (was it successful or not? Reaction StoichiometryHOIn practice, it is best to use a 50-100% excess of . Purposive Communication Module 2, TOP Reviewer - Theories of Personality by Feist and feist, 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. The camphor is then reduced by sodium borohydride to give the isomeric alcohol isoborneol. 1952, 75, 186. Oil, Moles of NaBH 4 = (mass) / (molar mass) Experiment 2 post lab report; Lab 4 borohydride reduction; Mercedes Izquierdo Orgo 2 Prelab 1; Expierment 3 lab report Thompson, Karla . We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. State why we employ NaBH . solution did not precipitate due to having too low of a pH (0) or from poor mixing of the Theoretical yield of 2-methylcyclohexanol Alcohols are formed from the reduction of carbonyl compounds. In one-step, there is a nucleophilic attack of a hydride ion on the electrophilic carbonyl carbon; and the protonation of the resulting alkoxide by water or some other acid (ex. Reduction reactions can be used in the pharmaceutical field & applied directly in the The anions tend to attack sterically hindered compounds from the least sterically hindered side. Chemistry. JOURNAL OF CHEMICAL EDUCATION, no. j. change in lens shape to focus retinal image Give the IR spectra of vanillin, Propanal (CHacHzCHO) is used in the pharmaceutical industry to make essential ingredients, organic chemicals, industrial chemicals, pesticides. It would be great to convert this table to text. Chem. Observe & recorde Rf using Iodine. Introduction: Popular reducing agents used in organic chemistry are lithium aluminum hydride (LiAlH. Become Premium to read the whole document. @5Bq>3~ Fp! H O HO H 3CO 1. Vanillin is an aromatic compound r4RJ3FU6`xqi$*8lBU[@PzB Apy 3YSJr 6y|; 2021-22, Hesi fundamentals v1 questions with answers and rationales, (Ybaez, Alcy B.) 51 51 Clear Visvous Copyright 2023 StudeerSnel B.V., Keizersgracht 424, 1016 GC Amsterdam, KVK: 56829787, BTW: NL852321363B01, Forecasting, Time Series, and Regression (Richard T. O'Connell; Anne B. Koehler), Principles of Environmental Science (William P. Cunningham; Mary Ann Cunningham), Psychology (David G. Myers; C. Nathan DeWall), Chemistry: The Central Science (Theodore E. Brown; H. Eugene H LeMay; Bruce E. Bursten; Catherine Murphy; Patrick Woodward), Biological Science (Freeman Scott; Quillin Kim; Allison Lizabeth), Brunner and Suddarth's Textbook of Medical-Surgical Nursing (Janice L. Hinkle; Kerry H. Cheever), Give Me Liberty! In this procedure, NaBH4 adds hydride to the carbonyl carbon of vanillin. Spec2D: A Structure Elucidation System Based on 1H, NMR and HH COSY Spectra in Organic Chemistry. This is a Premium document. All the data collected from the Melting point, to the H NMR & IR obtained shows great g. site of sharpest vision - perform carbonyl reduction using the reducing agent, NaBH4. Reduction is the addition of hydrogen atoms Draw the full mechanism of the sodium borohydride reduction of vanillin. CHEM-269 Reduction of Benzoin Dr. Chris McDaniel . Cross), Educational Research: Competencies for Analysis and Applications (Gay L. R.; Mills Geoffrey E.; Airasian Peter W.), Chemistry: The Central Science (Theodore E. Brown; H. Eugene H LeMay; Bruce E. Bursten; Catherine Murphy; Patrick Woodward), Civilization and its Discontents (Sigmund Freud), Organic Chemistry I Laboratory (CHEM 253). To reduce the aldehyde in vanillin into the alcohol functional group in vanillyl alcohol, sodium borohydride was used instead of lithium aluminum hydride (LAH). Please draw the product of the reaction and place the deuterium in the proper location. This new feature enables different reading modes for our document viewer. m. sense of smell methyl groups. Transfer to mixture to separatory Vanillin is an aromatic compound found in vanilla and is used in artificial vanilla flavoring. 3. How did the 2 reactions differ? 4 0 obj x[qW43A5 Ajc|vk'%C"MN9ug__~CS^0T[hjV/V_PWC7~iS5WU7Mu}}7USStdf^O[0f3?APh537Li1X==d= XuB+.i37Q_wU~c~1XKqTzqJ&zb5& We performed a synthesis of methyl diantilis lab. Print. 0.98 grams of Camphor was dissolved in 15 mL of ethanol. An excess of sodium borohydride, a convenient and mild reducing agent, will be used as the reductant in this reaction. With the guidance of your GSI determine an appropriate solvent for recrystallization. Organic synthesis activity Organic Synthesis Experimental Activity: EAS Reaction Watch the following videos from the Second Semester Organic Chemistry Lab at Eastern Kentucky University, U.S. Identify and describe three social characteristics associated with alcohol consumption. ***Note that if there is no reaction for that lab (if we are doing a separation), this section In such a case, also replace, Because there are less moles of vanillin, it is the limit, Principles of Environmental Science (William P. Cunningham; Mary Ann Cunningham), The Methodology of the Social Sciences (Max Weber), Forecasting, Time Series, and Regression (Richard T. O'Connell; Anne B. Koehler), Psychology (David G. Myers; C. Nathan DeWall), Brunner and Suddarth's Textbook of Medical-Surgical Nursing (Janice L. Hinkle; Kerry H. Cheever), Biological Science (Freeman Scott; Quillin Kim; Allison Lizabeth), Campbell Biology (Jane B. Reece; Lisa A. Urry; Michael L. Cain; Steven A. Wasserman; Peter V. Minorsky), Give Me Liberty! secondary alcohol). The Synthesis and Characterization of Carbonyl Compounds, { "00:_Front_Matter" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "1:_Acetylation_of_Aniline_(Experiment)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "2:_Reduction_of_Organic_Compounds_(Experiment)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "3:_Esterification_(Experiment)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "4:_The_Aldol_Condensation_\u2013_Preparation_of_Chalcones__(Experiment)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "5:_Identification_of_a_Spectroscopic_Unknown_(Experiment)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "6:_The_Wittig_Reaction_(Experiment)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "7:_The_Grignard_Reaction_(Experiment)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Preliminaries : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "zz:_Back_Matter" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, { Experiments : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Intermediate_Chemical_Experimentation : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Lab_I : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Lab_II : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Misc : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", The_Synthesis_and_Characterization_of_Carbonyl_Compounds : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, 2: Reduction of Organic Compounds (Experiment), [ "article:topic", "reducing agents", "showtoc:no", "license:ccbysa", "authorname:gshultz", "lithium aluminum hydride", "sodium borohydride" ], https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FAncillary_Materials%2FLaboratory_Experiments%2FWet_Lab_Experiments%2FOrganic_Chemistry_Labs%2FThe_Synthesis_and_Characterization_of_Carbonyl_Compounds%2F2%253A_Reduction_of_Organic_Compounds_(Experiment), \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}\) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\), Describe in your own words what happened to your ketone as NaBH. Both reagents were discovered by Schlesinger in the 1940s and are routinely used in organic synthesis. The experiment did not go entirely as planned, namely in that our solution did not precipitate. In this experiment you will convert a chiral alcohol into its chiral diastereomer using a scheme involving oxidation to the ketone followed by stereoselective reduction to the diastereomer . To dissolve the vanillin, stir the glass-rod by gently warming the. Course Hero is not sponsored or endorsed by any college or university. T+5-0dj@?5W (tExZjIU_&unS~/fhz q;Mtt?~#bAp 5 ~ 1 cm . Therefore, the vacuum filtration produced (G=gA,TpZz'=?JM/M~B3-EA10kXKA5Wtx(:H Remove the magnesium sulfate by gravity filtration and evaporate the organic solvent by applying a stream of nitrogen gas. Because there are less moles of vanillin, it is the limiting reagent. Lab TA: Copyright 2023 StudeerSnel B.V., Keizersgracht 424, 1016 GC Amsterdam, KVK: 56829787, BTW: NL852321363B01, Lab 10: Reduction of Vanillin to Vanillyl Alcohol. Hint: one H on the alcohol comes from a hydride and the other comes from the acidic proton on CH3CH2OH (ethanol). To reduce vanillin to form vanillyl alcohol and characterize the sample using HNMR and Using Green Chemistry to minimize the use and generation of hazardous substances as chemical products, we converted vanillin into vanillyl alcohol . attached to the main compound, in this case the alcohol to cyclohexanol, that hydrogen is useful Reduction is the addition of hydrogen atom, or loss of hydrogen atoms, or both. LiAlH4 also requires a separate acidic work up step where reduction with NaBH4 does not. and we had to use another groups product to determine melting point. Three of the unknown aromatic ketones should produce liquid products after reduction. now becomes oxidised. and fragrance preparation, the finest vanilla is obtained from natural vanilla, however synthetic vanillin costs much less. 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. 7th ed. Experiment 1: Sodium Borohydride Reduction of Vanillin: A Low Solvent Synthesis of Vanillyl Alcohol Vanessa Kenealy Chem 142 Date preformed: February 4, 2015 Introduction: Vanillin (4-hydroxy-3-methoxybenzaldehyde) is a pleasant smelling aromatic compound formed through the enzymatic breakdown of a glucoside during the curing process of the vanilla bean. The experiment was followed verbatim from the lab manual as found on pages 86-89, To first start off this experiment, the TLC plate needs to be prepared by drawing, the basline and marking the locations for sample spots with a pencil (S.M., Co, and, Rxn). production of benign pesticides when isolated. Brooke Vitale. Am. Your objective is to determine if the ketone unknown can be reduced by NaBH4 to form an alcohol, to compare the two reactions (part 1 and part 2), and to determine the identity of the unknown ketone. 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. 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We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. 2021-22, 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. 1.055 grams of sodium borohydride was added was slowly added to . Aldehydes produce 1-alcohols and ketones produce 2-alcohols. NaBH4 can be a severe skin and eye irritant; breathing the compound can irritate the nose and throat. The variation in heights on the graph is related to the amount of hydrogen present in the functional groups. Experiment 7. Noor Kanter hbbd``b`$e r H0/Il@t"B@LCS&FW@#n?c/ To reduce vanillin to form vanillyl alcohol and characterize the sample using HNMR and CNMR. Percent yield = (actual yield) / (theoretical yield) x For example, reduction of bicyclo[2.2.1]heptan-2-one yields a mixture of two alcohols in which the endo compound predominates. viscous. Transfer your product carefully and . HW[o6~'p-`E(8-K[. Proper safety precautions must be taken in this lab. The reaction will be followed using TLC analysis, and the purity of. NaBH4 can be a severe skin and eye irritant; breathing the compound can irritate the nose and throat. secondary alcohol (borneol) to a ketone (camphor). How does the Infrared spectrum of 9-fluorenone compare to its alcohol product? known as Reduction. Sodium borohydride and lithium aluminum hydride have only moderate stereoselectivity. Organic Chemistry Lab UHCL (Labs 6-10+IR/NMR/, Experiment 15 - Hydrogenation of Castor Oil, Experiment 13 - Synthesis of Ethanol by Ferme, Cell Organelle and Processes Review Sheet. mass, calculate the percent yield, Ketone Reduction by Sodium Borohydride: 3-Nitroacetophenone and 9H-Fluoren-9-one Introduction: The reduction of aldehydes, ketones, and esters is a fundamental transformation often used in organic synthesis. Purpose To reduce vanillin to form vanillyl alcohol and characterize the sample using HNMR and CNMR.. bxBTxOl{]jN %mlh'{n>wrY`sIQ;ceXDO hydogentation. Weigh an clean and dry empty SMALL sample vial with cap. zx\0XJ The resulting alcohol may be the desired final product, or it may d. rotational movements Add 4-5 mL of diethyl ether to the mixture and mix to allow the product to migrate into the organic layer. Methylcyclohexanone. workup, an alcohol is the product. to pre-weighted filter flask, vacuum Soc. The solution our hbbd``b`NU@AD'`iqY * + @' H5l{R`q`Li w endstream endobj startxref 0 %%EOF 214 0 obj <>stream These are both white (or near white) solids, which are prepared from lithium or sodium hydrides by reaction with aluminum or boron halides and esters. It can also irritate the lungs and cause coughing/shortness of breath. Pipet out the ether layer and dry it over anhydrous magnesium sulfate. Report 10: Reduction of Vanillin to Vanillyl Alcohol. Vanilla is commonly used in fragrances and foods. ]eDT In this procedure, NaBH4 adds secondary alcohol). hw[I(c8'I^V0{`jl0daVm(4+_T0rQX] -C 5PS 23MhCqW~(o?Nbc iNs|"shEd=?&>jaka6h]3T0USff=on 5j"Vkrk+6\jgvv#,-9k`H_+&w[5y$&q=_9mF/ ;m^MNC ku+/P{d}:AxR{=jPW{Ah.m*eK?ME|ab,)/$;&1Cu:C\$7_Bj;n-{nuigYPKr7K#!fo Amounts: 2 g Vanillin Complete the Notebook Pre-lab PRIOR to coming to the lab. The NaBH4 and NaOH solution failed to precipitate significantly in the ice bath even after scratching the side of the flask multiple times. Some reducing agents are DIBAL-H (strong) LiAlH . in determing so. +@ after scratching the side of the flask multiple times. IbRYjLj\2ibBz7Lqb1t draw an explain the mechanism of Sodium Borohydride Reduction of Vanillin Acetate. ea`(s| i7d$@[SFXDCF[R)/4/eT1pax aF$#/x+f7@fde``~w0(@ " Addition of a hydride anion (H:-) to an aldehyde or ketone gives an alkoxide anion, which on protonation yields the corresponding alcohol. Run TLC to determine if the reaction is obtain an IR & H NMR, Results: 2210L AND CHM2211L Fall 2017, Spring 2018, Summer 2018. hydride to the carbonyl carbon of vanillin. alcohol from vanillin involves the reduction of an aldehyde to form a primary alcohol, or the 0 moles x 112 g/mol = 0 g This one is a bit more complicated and there are many new techniques. 9-Fluorenone Lab Report 382 Words | 2 Pages. Explain why it is better, describe the experiment of "Sodium Borohydride Reduction of Vanillin Acetate".
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