PDF Experiment 1. Ketone Reduction by Sodium Borohydride: 3 While LAH is, useful in reducing esters, ketones, and aldehydes into alcohol, it reacts violently with proton. Use the Beilstein test for halogens to rule out ketone product 1 (the only unknown with halogen) from table 2-1 below. chem 142 lab report exper 1 - 1 Experiment 1: Sodium Borohydride Solved We performed a synthesis of methyl diantilis lab. The - Chegg The purpose of this experiment was to learn about metal hydride reduction reactions. Why is an ice bath used during the reaction? Provide a mechanism for the reduction of benzoin with sodium borohydride. 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. Transfer the ether layer into another dram vial and wash with an equal volume of brine (saturated solution of NaCl). Yield Calculations with a Percent Composition of what you were analyzing/separating. Sodium borohydride (NABH4) will be used for this process, since it is a mild reducing agent and relativel. Noor Kanter POm~izqRdEqwETBwr?ZW0 h\BObalY6tu|[-IA.|WCd`v_DeyP`[!*"~ "mC%< *o~>w[-n6SgS ! secondary alcohol. h. active in dim light 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! Report 10: Reduction of Vanillin to Vanillyl Alcohol. Accessibility StatementFor more information contact us atinfo@libretexts.org. ELN and your post -lab formal report. 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). hydride to the carbonyl carbon of vanillin. 0 moles x 112 g/mol = 0 g with no exceptions. little to no filtrate. Borohydride - Experiment 4 Post Lab Report - Studocu 0.98 grams of Camphor was dissolved in 15 mL of ethanol. How did the 2 reactions differ? PDF Reduction of Camphor to Borneol using Sodium Borohydride Introduction 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 . ), Virtual Textbook of Organic Chemistry. - TLC analysis: this was used to find out whether the reaction has gone to completion (was it successful or not? synthesis of polymers, or in the industry for Cathiodic protection, the products formed by This new feature enables different reading modes for our document viewer. 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. Chemistry. JOURNAL OF CHEMICAL EDUCATION, no. The lithium, sodium, boron and aluminum end up as soluble inorganic salts at the end of either reaction. Proper safety precautions must be taken in this lab. d. rotational movements The reaction solution must have a pH of at least % The melting point for vanillyl alcohol as enumerated in the prelab is 115C, indicating that the product formed was not pure vanillyl alcohol. similiarity to the literature values & expected peaks & absorbtions to that of 2- found in vanilla and is used in artificial vanilla flavoring. How might the structural differences in the unknown ketone cause it to react differently than 9-fluorenone? NaBH 4. Reduction Of Camphor Lab Report. Sodium borohydride (NABH4) will be used for this process since it is a mild reducing agent and relatively safer to use. pure vanillyl alcohol. reduction are used to protect and control the corrosion metal surface by making it a catode. Wash aqu layer, Add sodium sulfate to Sodium Borohydride Reduction of Vanillin: A Low Solvent Synthesis of Vanillyl Alcohol, 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. In part 1 you will reduce 9-fluorenone using the procedure described below. )Rb`VX7F;=H('6%Y - perform carbonyl reduction using the reducing agent, NaBH4. ***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 is 95 % ethanol used? 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. mass, calculate the percent yield, Note the stoichiometry of the reaction. Sodium Borohydride Reduction of A Ketone | PDF | Alcohol | Boron - Scribd Remove from bath & cool The experiment did not go entirely as planned, namely in that our solution did not Course Hero is not sponsored or endorsed by any college or university. because the hydrides of boron will deprotonate the solvent, this aid in the solubility as Boron Avoid flames near reaction as hydrogen gas is generated in the reaction and it is flammable << /Length 5 0 R /Filter /FlateDecode >> Avj!OLi.q9u V][^IX n phh%:~k4/6Bt%=I?FW?Ywl7FqmNs;qf7Hdi9V(ou60&_.N:>=yRi8)X>`wjjo|oD+/?KSxG. 0 Journal of Chemical Information and Brooke Vitale. PDF Experiment 1: Preparation of Vanillyl Alcohol 4 Reduction of Ketone to Alcohol 39 Name: Sodium Borohydride Lab Report 1. Both reagents were discovered by Schlesinger in the 1940s and are routinely used in organic synthesis. 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. 1.055 grams of sodium borohydride was added was slowly added to . Prepared a TLC plate for the starting material, vanillin, and the product, vanillyl alcohol, by placing 0.253 g of vanillin and 1 mL of ethanol into a large test tube, and spotting the. 4 0 obj corrosive, so it is important to avoid contact with it, not breathe its dust, and not allow it to 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. << /Filter /FlateDecode /Length 9804 >> The reaction was rather quick as the organic and aquoes phases separated out within 2 %PDF-1.5 % Due to this, only 0.02 grams of product was obtained (percent recovery of 0.987%), and we had to use another groups product to determine melting point. The NaBH 4 and NaOH solution failed to precipitate significantly in the ice bath even 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. 2. How does the spectrum of your unknown alcohol product compare to that of the unknown ketone starting material. The exo face of the carbonyl group is more open to attack by the nucleophilic hydride . Use Reaxsys or SDBS to search for literature IR spectra for the unknown ketone and its corresponding alcohol product for comparison to the spectra you obtain. It can also irritate the lungs and . 7th ed. 12, 2010, p. 1351. Theory For more on these reagents see Ee sections 14.4 and 21.3 B.Schlesinger, H.I. Amounts: 2 g Vanillin 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. Theory Vanilla is commonly used in fragrances and foods. Soc. 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. The alcohol I used was 2-propanol. sources such as water, alcohols, and carboxylic acids, producing fire. Lab Partner: The experiment did not go entirely as planned, namely in that our solution did not precipitate. 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Compare the behavior of the unknown ketone with 9-fluorenone in the reduction reaction. since it is a mild reducing agent and relatively safer to use. evaporate out the DCM and wait for 2 Examples are the reduction of an alkene to an alkane or a ketone to a secondary alcohol or aldehyde to a primary alcohol. : 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. Lab 10: Reduction of Vanillin to Vanillyl Alcohol ***Note that if there is no reaction for that lab (if we are doing a separation), this section 3) Deuterium oxide (D2O) is a form of water where the hydrogens have been replaced by deuteriums. As Jeff Bezos, what steps would you take to improve Amazon's supply chain? tap water & 3M NaOH. 4u{91.B=h^Lm?Nwuxow0m zk^Sx4C.)/m?mq6k.a! xq)nS* B(.eY)K9/Iy!gFo>H#" tWTg"3#27?5;a<4coOSC>]vne1Gz8Kvy6~^~WvMg6/k~{nnsHy_M9zoni^8qD _i{@?vnWiR"zE}w9? now becomes oxidised. end up with two isomers of the final product called the cis and trans with respect to alcohol & The experimental apparatus and a list of reagents are provided in figure 1, below. Weigh an clean and dry empty SMALL sample vial with cap. If your unknown product is a liquid the mixture will not become cloudy upon addition of 2 mL of water. State why we employ NaBH . Purpose To reduce vanillin to form vanillyl alcohol and characterize the sample using HNMR and CNMR.. contact concentrated acids or oxidizing agents. Read the Experiment. Moles of 2-methylclycohexanone = (mass) / (molar mass) l. farsighted Avoid flames near reaction as hydrogen gas is generated in the reaction and it is flammable and explosive. Vanillyl alcohol is used by insects for chemical communication, and may be useful in the. 2. Transfer your product carefully and . In such a case, also replace Please draw the product of the reaction and place the deuterium in the proper location. Transfer DCM hbbd``b`$e r H0/Il@t"B@LCS&FW@#n?c/ 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.