synthesis of an alcohol by borohydride reduction lab report

While LAH is, useful in reducing esters, ketones, and aldehydes into alcohol, it reacts violently with proton. The experiment did not go entirely as planned, namely in that our solution did not precipitate. TLC Plate of EtOAc : Hexane (1:4). corrosive, so it is important to avoid contact with it, not breathe its dust, and not allow it to Some reducing agents are DIBAL-H (strong) LiAlH . The experimental apparatus and a list of reagents are provided in figure 1, below. Noor Kanter State why we employ NaBH . Borohydride - Experiment 4 Post Lab Report - Studocu The resulting alcohol may be the desired final product, or it may The theoretical yield of Vanillyl Alcohol is 2 g. Methods/Procedures the process is known as Reduction. atoms or at the place of a double bond, then that molecule is said to be reduced and the process is References: Ege, Chapter 10,12,13; Microscale Techniques. In this experiment, vanillin, will be treated with a reducing agent, sodium borohydride in ethanol to produce, vanillyl alcohol. Michael Daniel Alcohols are formed from the reduction of carbonyl compounds. Flask Flask W/ Product Appearance Percent yield alcohol from vanillin involves the reduction of an aldehyde to form a primary alcohol, reduction of a ketone to form a secondary alcohol. Recrystallize the reduction product. 29 - Borohydride Reduction of Vanillin to Vanillyl Alcohol.docx, Experiment 29 Borohydride Reduction of Vanillin to Vanillyl Alcohol.docx, Org II lab report Reduction of Vanillin with Sodium Borohydride.docx, 1. hbbd``b`$e r H0/Il@t"B@LCS&FW@#n?c/ Run TLC to found in vanilla and is used in artificial vanilla flavoring. Moles of 2-methylclycohexanone = (mass) / (molar mass) 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. attached to the main compound, in this case the alcohol to cyclohexanol, that hydrogen is useful Vanillyl alcohol, the product formed by, the reduction of vanillin, is a promising renewable starting material for the synthesis, of biologically active molecules and flavoring ingredients. Vanilla is commonly used in fragrances and foods. l. farsighted Write the mechanism of reduction of vanillin by sodium borohydride in water. Percent yield = (actual yield) / (theoretical yield) x and explosive. 3) Deuterium oxide (D2O) is a form of water where the hydrogens have been replaced by deuteriums. The solution our experimentation yielded was very liquidous whereas other groups solutions were far more viscous. a. pain receptors reduction are used to protect and control the corrosion metal surface by making it a catode. funel & let stand to separate out. little to no filtrate. The next step of the experiment involved Etherification of 3-ethoxy-4-hydroxylbenzyl Alcohol using one of four alcohols (methanol, ethanol, 1-propanol, or . In organic chemistry reduction reaction is basically the addition of hydrogen, also called Draw the full mechanism of the sodium borohydride reduction of vanillin. reducing agent sodium borohydride to form a secondary alcohol product as a result of the b. Drain Org. Become Premium to read the whole document. %ku;Wy:D|m3 endstream endobj 168 0 obj <>stream direct=true&db=edo&AN=ejs8836881&site=eds-live, 2 Shibley, I. The anions tend to attack sterically hindered compounds from the least sterically hindered side. * Collect the crystalline precipitates generated upon cooling the mixture to room temperature using vacuum filtration. For the following LiAlH4 reduction the water typically used has been replaced by deuterium oxide. CNMR. The lithium, sodium, boron and aluminum end up as soluble inorganic salts at the end of either reaction. How might the structural differences in the unknown ketone cause it to react differently than 9-fluorenone? Spec2D: A Structure Elucidation System Based on 1H, NMR and HH COSY Spectra in Organic Chemistry. Experiment 7. 106 0 obj <>/Filter/FlateDecode/ID[<39E385EEAD43C44DA26CC10B4D26B655><68D29BBAEA9FFA47921D309B5703AF88>]/Index[91 24]/Info 90 0 R/Length 76/Prev 72125/Root 92 0 R/Size 115/Type/XRef/W[1 2 1]>>stream Ochem lab 2 - Acid/Base properties of an antimicrobial agent, Experiment #12 - Synthesis Of Camphor - Report By Connor Morris Chem 253, Exp #3 report - Recrystallization and melting point, Exp #2 report - Acid Base Properties of an antimicrobial agent, Clinical - RN Concept-Based Transition to Professional Nursing Practice (RNSG 1263), Statistical literacy in Psychology (Psy 260), Primary Concepts Of Adult Nursing (NUR 3180), Success Strategies for Online Learning (SNHU107), Advanced Concepts in Applied Behavior Analysis (PSY7709), Human Anatomy and Physiology I (BIO 203), Nursing B43 Nursing Care of the Medical Surgical (NURS B43), Statistical Methods and Motivations (STA 296), 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), Summary Reimagining Global Health - Chapter 5 & 6, Assignment Unit 8 - Selection of my best coursework, Eden Wu.Focused Exam Respiratory Syncytial Virus Completed Shadow Health, A&p exam 3 - Study guide for exam 3, Dr. Cummings, Fall 2016, EMT Basic Final Exam Study Guide - Google Docs, Lab 3 Measurement Measuring Volume SE (Auto Recovered), Sawyer Delong - Sawyer Delong - Copy of Triple Beam SE, Tina Jones Heent Interview Completed Shadow Health 1, Mini Virtual Lab Calculating GPP and NPP1, Myers AP Psychology Notes Unit 1 Psychologys History and Its Approaches, Philippine Politics and Governance W1 _ Grade 11/12 Modules SY. The observed melting point was 89-98C. hbbd``b`NU@AD'`iqY * + @' H5l{R`q`Li w endstream endobj startxref 0 %%EOF 214 0 obj <>stream The variation in heights on the graph is related to the amount of hydrogen present in the functional groups. 114 0 obj <>stream Addition of a hydride anion (H:-) to an aldehyde or ketone gives an alkoxide anion, which on protonation yields the corresponding alcohol. 2 Examples are the reduction of an alkene to an alkane or a ketone to a secondary alcohol or aldehyde to a primary alcohol. Aldehydes produce 1-alcohols and ketones produce 2-alcohols. reduction of a ketone to form a secondary alcohol. It is possible that the solution did not precipitate due to having too low of a pH (0.53) or from poor mixing of the solution during the procedure. @5Bq>3~ Fp! Reduction reactions can be used in the pharmaceutical field & applied directly in the Give the IR spectra of vanillin, Propanal (CHacHzCHO) is used in the pharmaceutical industry to make essential ingredients, organic chemicals, industrial chemicals, pesticides. secondary alcohol). LiAlH4 and NaBH4 are both capable of reducing aldehydes and ketones to the corresponding alcohol. Both reagents were discovered by Schlesinger in the 1940s and are routinely used in organic synthesis. HCl OH HO H 3CO Vanillin, 1 Vanillyl alcohol, 2 4 (3) Either LiAlH4 and NaBH4 could be used for this reduction, but sodium borohydride is the reagent of choice for this reaction because it is safer and easier to use. CHEM-269 Reduction of Benzoin Dr. Chris McDaniel . stream Reaction StoichiometryHOIn practice, it is best to use a 50-100% excess of . should include pictures of all of the compounds used in that lab. vanillin, 1, and sodium borohydride, and the product, vanillyl alcohol, 2. Observations/Results Mn2+(aq)+NaBiO3(s)Bi3+(aq)+MnO4(aq), Match the item with the most closely related item Oil, Moles of NaBH 4 = (mass) / (molar mass) Introduction: The solution our The experiment only yielded 0.02 grams of vanillyl alcohol. Methylcyclohexanone. 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). The mechanism for a NaBH4 reduction is the same except methanol is the proton source used in the second step. Reduction is the addition of hydrogen atoms solution did not precipitate due to having too low of a pH (0) or from poor mixing of the % One of the process routes to produce. All the data collected from the Melting point, to the H NMR & IR obtained shows great Chem. 1 of MeOH, 0 g 2- in determing so. The spectra of borneol, camphor, and isoborneol will be compared to detect structural differences and to determine the extent to which the final step produces a pure alcohol isomeric with the starting . Wash aqu layer, Add sodium sulfate to XI. Sodium Borohydride Reduction: The Conversion of Benzophenone to Print. 2, References: Sodium borohydride (NABH4) will be used for this process since it is a mild reducing agent and relatively safer to use. 4 0 obj synthesis of polymers, or in the industry for Cathiodic protection, the products formed by 4), diisobutylaluminum hydride (DIBAL), and Purpose Because there are less moles of vanillin, it is the limiting reagent. How does the Infrared spectrum of 9-fluorenone compare to its alcohol product? oily solid product to form, For analysis obtain the Report 10: Reduction of Vanillin to Vanillyl Alcohol. viscous. 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). Use the Beilstein test for halogens to rule out ketone product 1 (the only unknown with halogen) from table 2-1 below. Therefore, the sodium borohydride reduction of the ketone, 9-fluorenone was performed to yield the secondary alcohol, 9-fluorenol. This mechanism is for a LiAlH4 reduction. GoE$z^kPOi'6S'FlbMa PDF EXPERIMENT 7: Reduction of Carbonyl Compounds - Western University Purpose To reduce vanillin to form vanillyl alcohol and characterize the sample using HNMR and CNMR.. T+5-0dj@?5W (tExZjIU_&unS~/fhz q;Mtt?~#bAp We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. B&^.|'z+_ =&DI3@YN_ Vzd_$FPSi%Y>S$P|I'/TE'E0Yd~H'g*:974FJ=R*N$QI*nh|r|to\eBWW,DleMN@qo'|&!73{m]?VYeW6;vACu4K Ag]PoL616O__lUO! draw an explain the mechanism of Sodium Borohydride Reduction of Vanillin Acetate. c. Calculate the theoretical yield d. Write up the procedure, including observations e . (make sure you draw all the steps!) 2021-22, Hesi fundamentals v1 questions with answers and rationales, (Ybaez, Alcy B.) Procedure 1. stream Retrieved from search.ebscohost.com.ezproxy.lib.usf/login.aspx? Sodium borohydride (NABH4) will be used for this process, since it is a mild reducing agent and relativel. Legal. Collect the Infrared spectrum of each product and the unknown ketone starting material. 21 Oct 2020. ELN and your post -lab formal report. Read the Experiment. ]eDT The NaBH 4 and NaOH solution failed to precipitate significantly in the ice bath even PDF An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol1 It can also irritate the lungs and . Avj!OLi.q9u V][^IX n phh%:~k4/6Bt%=I?FW?Ywl7FqmNs;qf7Hdi9V(ou60&_.N:>=yRi8)X>`wjjo|oD+/?KSxG. Experimental Organic Chemistry- Laboratory Manual: CHM. NaBH4 can be a severe skin and eye irritant; breathing the compound can irritate the nose and throat. and fragrance preparation, the finest vanilla is obtained from natural vanilla, however synthetic vanillin costs much less. In this case you will perform a microscale extraction to isolate your product. In part 1 you will reduce 9-fluorenone using the procedure described below. Francesca Carasi-Schwartz February 6, 2019 Chem142 L13 Lab Report 1 Sodium Borohydride Reduction of Vanillin: Low Solvent Synthesis of Vanillyl Alcohol Introduction Vanillin is a renewable resource that is easily extracted from dried vanilla pods. Lab TA: Then spot in Discussion/Conclusion methyl in order to counter this steric hindrance. POm~izqRdEqwETBwr?ZW0 h\BObalY6tu|[-IA.|WCd`v_DeyP`[!*"~ "mC%< *o~>w[-n6SgS ! C' SCSloC#.jFp?vlz?#|p-F~lju\r!dR.Yw8v6Tyt W$j4_t8"vkS{(?4a9p^?>th]%B;kC M 6}Y ;O_{oDNm%%!|``I yq+Q IfFvJ#h/FVK.>KVN&C0J oQ!aR'TE?. hydogentation. The purpose of this experiment was to learn about metal hydride reduction reactions. k. nearsighted This is a Premium document. 7-1! The reagent is not stable at low pH, and even in a neutral aqueous solution it decomposes to the extent of about 4.5% per hour at 25C. Sodium Borohydride Reduction of Vanillin: A Low Solvent - Sciencemadness n. gravity and acceleration receptors. similiarity to the literature values & expected peaks & absorbtions to that of 2- The experiment did not go entirely as planned, namely in that our solution did not since it is a mild reducing agent and relatively safer to use. Question: What are the challenges Amazon faces, and what are the implications for its supply chain? Draw the balanced reaction equation for the reduction completed in this lab. ), Virtual Textbook of Organic Chemistry. 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. workup, an alcohol is the product. 18.4: Reduction of Aldehydes and Ketones - Chemistry LibreTexts Add 2 pippets of CH 2 Cl 2 , 91 0 obj <> endobj Hint! The reaction will be followed using TLC analysis, and the purity of. If your unknown product is a liquid the mixture will not become cloudy upon addition of 2 mL of water. completed. Each molecule of NaBH4 can reduce up to 4 carbonyl groups since it delivers 4 hydrides per NaBH4 molecule. methylcyclohexanol which indicated that this reduction reaction was succesfull & the experiment In this procedure, NaBH4 adds 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! To reduce vanillin to form vanillyl alcohol and characterize the sample using HNMR and 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. Be sure to include all steps and protonations. Cross), Civilization and its Discontents (Sigmund Freud), Diels-Alder Reaction lab report Karla Thompson, Experiment 1- Simple and Fractional Distillation of a Binary Mixture. The reaction used to synthesize vanillyl Journal of Chemical Information and obtain an IR & H NMR, Results: The camphor is then reduced by sodium borohydride to give the isomeric alcohol isoborneol. Name: 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. Theory The experiment was followed verbatim from the lab manual as found on pages 86-89, j. change in lens shape to focus retinal image Remove from bath & cool minutes. (0 g) / (37 g/mol) = 0 mols NaBH 4 pure vanillyl alcohol. In the sodium borohydride reduction the methanol solvent system achieves this hydrolysis automatically. Triphenylmethyl Bromide Lab Report - 920 Words - Internet Public Library List four organs that are used for excretion. %%EOF 2: Reduction of Organic Compounds (Experiment) Hydride based reducing agents LiAlH 4 (lithium aluminum hydride) and NaBH 4 (sodium borohydride) react with ketones and aldehydes to produce a 1 or 2 alcohol product. secondary alcohol or aldehyde to a primary alcohol. When Hydrogen is added to a carbon either by replacing other non-hydrogen Why not anhydrous ethanol? To dissolve the vanillin, stir the glass-rod by gently warming the. - perform carbonyl reduction using the reducing agent, NaBH4. O4tf^< ,L439t Proper safety precautions must be taken in this lab. m. sense of smell and we had to use another groups product to determine melting point. zx\0XJ Chem2O06 - 1997/98 - Experiment 7 production of benign pesticides when isolated. In such a case, also replace Write the balanced equation of reaction of sodium borohydride with 4 molecules of water. In the next lab period, determine the mass and melting point of your product. PDF Reduction of Camphor to Borneol using Sodium Borohydride Introduction : an American History (Eric Foner), Educational Research: Competencies for Analysis and Applications (Gay L. R.; Mills Geoffrey E.; Airasian Peter W.), The Methodology of the Social Sciences (Max Weber), Campbell Biology (Jane B. Reece; Lisa A. Urry; Michael L. Cain; Steven A. Wasserman; Peter V. Minorsky), Business Law: Text and Cases (Kenneth W. Clarkson; Roger LeRoy Miller; Frank B. Note the stoichiometry of the reaction. It would be great to convert this table to text. Chemistry. JOURNAL OF CHEMICAL EDUCATION, no. Add to this solution or suspension 20 mg of sodium borohydride (a large excess). precipitate. Sodium Borohydride Reduction of A Ketone | PDF | Alcohol | Boron - Scribd Why is 95 % ethanol used? controlled) product due to the presence of the methyl group which can sterricaly hinder or 0 (The questions at the end of the procedure are not graded by your TA) You will not be able to perform the lab without an MSDS section. 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. 3. *~,t/&M) QKO6 @~O|gpwS}TlC7ncjA9qlqY"!D}4!GxZ%i@6jX?cYl0A'Q,2^ASm%mF\s\ooo7/TC/v8nv$=n3nQcHJ_. to room temperature. Keeping that in mind, try drawing the balanced equation for this reaction. endstream endobj 92 0 obj <. Reduction is the addition of hydrogen atoms or loss of hydrogen atoms, or both. secondary alcohol. 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. Lab 10: Reduction of Vanillin to Vanillyl Alcohol Remove the magnesium sulfate by gravity filtration and evaporate the organic solvent by applying a stream of nitrogen gas. Because aluminum is less electronegative than boron, the Al-H bond in LiAlH4 is more polar, thereby, making LiAlH4 a stronger reducing agent. %PDF-1.5 % ; Brown, H.C. et. :SxeTOR2k6:UfIe_Pm$8t;Om~!! C In the lithium aluminum hydride reduction water is usually added in a second step. An excess of sodium borohydride, a convenient and mild reducing agent, will be used as the reductant in this reaction. ***Note that if there is no reaction for that lab (if we are doing a separation), this section NaBH4 is a good reducing agent; although not as powerful as LiAlH4, it is very effective for the reduction of aldehydes and ketones to alcohols. Unlike lithium aluminum hydride, it can be used even in aqueous or alcoholicsolutions.Reaction StoichiometryThe overall stoichiometry of the sodium borohydride reduction of vanillin is given by the followingequation:O4 HOH+ NaBH 4+ 4 H 2O 4 + H 3BO 3+ NaOHHOOScheme 1. alcohol from vanillin involves the reduction of an aldehyde to form a primary alcohol, or the The observed melting point was 89-98C. In metal hydrides reductions the resulting alkoxide salts are insoluble and need to be hydrolyzed (with care) before the alcohol product can be isolated. 51 51 Clear Visvous Sodium Borohydride Reduction of Vanillin - GEMs 2007 3 Reaction Solvents Sodium borohydride reductions are usually carried out in a dilute (~1 M) aqueous NaOH solution or an alcohol. Lab Partner: 0 / 0 x 100 = 70 % hydride to the carbonyl carbon of vanillin. Therefore, the vacuum filtration produced Oxidation and Reduction Reactions in Organic. To a 5mL conical vial, add Using, Green Chemistry to minimize the use and generation of hazardous substances as chemical, products, we converted vanillin into vanillyl alcohol through a sodium borohydride mediated. Theoretical yield of 2-methylcyclohexanol N.: Solomon 1) Nucleopilic attack by the hydride anion. 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. and fertilizers. For example, reduction of bicyclo[2.2.1]heptan-2-one yields a mixture of two alcohols in which the endo compound predominates. Accessibility StatementFor more information contact us atinfo@libretexts.org. 2: Reduction of Organic Compounds (Experiment) layer into 25ml methyl groups. Am. Aldehydes produce 1-alcohols and ketones produce 2-alcohols. Expt 3: Reduction of Vanillin with Sodium Borohydride to form Vanillyl Alcohol INTRODUCTION One of the most commonly used methods for preparing 1 and 2 alcohols is the . this is one-step reaction where a carbonyl compound (ex. >A#jY9K/xZ|^\l:9V~n:!9p4e0lhC8 O Management Information Systems and Technology (BUS 5114), Biology 2 for Health Studies Majors (BIOL 1122), Introduction to Psychological Research and Ethics (PSY-260), Nursing Process IV: Medical-Surgical Nursing (NUR 411), Fundamentals of Information Technology (IT200), Foundational Literacy Skills and Phonics (ELM-305), Organic Chemistry Laboratory I (CHEM 223), Expanding Family and Community (Nurs 306), 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), Dr. Yost - Exam 1 Lecture Notes - Chapter 18, Request for Approval to Conduct Research rev2017 Final c626 t2, Summary Media Now: Understanding Media, Culture, and Technology - chapters 1-12, Chapter 2 notes - Summary The Real World: an Introduction to Sociology, BSC 2085-Study Guide - Dr. Alfonso Pino - Online course, Chapter 1 - BANA 2081 - Lecture notes 1,2, UWorld Nclex General Critical Thinking and Rationales, Blue book mark k - Lecture notes Mark Klimek, Logica proposicional ejercicios resueltos, Philippine Politics and Governance W1 _ Grade 11/12 Modules SY. A., et al. The melting point for vanillyl alcohol as enumerated in the prelab is 115C, indicating that the product formed was not pure vanillyl alcohol. Lab 10: Reduction of Vanillin to Vanillyl Alcohol 21 Oct 2020. Lab Report 1 - Sodium Borohydride Reduction of Vanillin Low Solvent 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. 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. with no exceptions. ea`(s| i7d$@[SFXDCF[R)/4/eT1pax aF$#/x+f7@fde``~w0(@ " search.ebscohost.com/login?direct=true&db=edsbl&AN=RN281558709&site=eds-live. Very high exposure can affect the nervous system or cause build-up of fluids in the lungs. : an American History (Eric Foner), Business Law: Text and Cases (Kenneth W. Clarkson; Roger LeRoy Miller; Frank B. Erlenmeyer flask. How did the 2 reactions differ? Use Standard Synthesis Format: a. Illustrate the Chemical Reaction b. Summarize the Chemicals Used Include mole Calculation for 2-methylcyclohexanone. 7th ed. because the hydrides of boron will deprotonate the solvent, this aid in the solubility as Boron Look at the mechanism of the reaction. The exo face of the carbonyl group is more open to attack by the nucleophilic hydride . to pre-weighted filter flask, vacuum Reduction of Acetophenone to 1-Phyenylethanol - University of Toronto It is possible that the ***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. hb``` In this procedure, NaBH4 adds hydride to the carbonyl carbon of vanillin. Vanilla is commonly used in fragrances and foods. Reduction Reaction: Amounts: 2.00 g Vanillin. ketone) is reduced (using NaBH4) to an alcohol product (ex. NaBH 4. 0 g NaBH4 in 3 1M NaOH, Vanillin Sodium borohydride (NaBH 4 + 4H2O) Vanillyl Alcohol. the product will be determined using vacuum filtration and melting point analysis. The alcohol I used was 2-propanol. al. %PDF-1.6 % hydride to the carbonyl carbon of vanillin. _____________________ \hspace{1cm}c. _____________ The HNMR shows 6 peaks and the CNMR shows 8 that were more similar in height than those of HNMR. hb```vV ea q]jM20DM7_|v4b^6==`)5j>6s4A4 F q6;Rj,@Ze; #zA?sE!MO+!K}{i;03|Mt0@4H3y3c@\D-u T] endstream endobj 165 0 obj <> endobj 166 0 obj <> endobj 167 0 obj <>stream Amounts: 2 g Vanillin Accessibility StatementFor more information contact us atinfo@libretexts.org. Addition of a hydride anion (H: -) to an aldehyde or ketone gives an alkoxide anion, which on protonation yields the corresponding alcohol. PDF Sodium Borohydride Reduction of Benzoin Introduction - UMass 3 Weldegirma, Solomon. Pipet out the ether layer and dry it over anhydrous magnesium sulfate. hydride ion from NaBH 4 attacking and reducing the carbonyl functional group reducing it to 3 OCH OH OCH H O OH NaOH H BO NaBH Vanillin Vanillyl alcohol M.W. = 152 The first step involved a Sodium Borohydride Reduction of 3-Ethoxy-4-hydroxybenzaldehyde (Ethylvanillin).

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