% 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. If you have a suspension the suspended ketone solid will dissolve. - perform carbonyl reduction using the reducing agent, NaBH4. *~,t/&M) QKO6 @~O|gpwS}TlC7ncjA9qlqY"!D}4!GxZ%i@6jX?cYl0A'Q,2^ASm%mF\s\ooo7/TC/v8nv$=n3nQcHJ_. NaBH4 is a milder reducing agent than LiAlH4 and can be used in protic solvents, such as ethanol. stream In metal hydrides reductions the resulting alkoxide salts are insoluble and need to be hydrolyzed (with care) before the alcohol product can . layer into 25ml Vanillin is an aromatic compound found in vanilla and is used in artificial vanilla flavoring. Write your answer at the end of your lab notebook pages for this experiment: This page titled 2: Reduction of Organic Compounds (Experiment) is shared under a CC BY-SA license and was authored, remixed, and/or curated by Ginger Shultz. )Rb`VX7F;=H('6%Y secondary alcohol). :SxeTOR2k6:UfIe_Pm$8t;Om~!! C Draw the full mechanism of the sodium borohydride reduction of vanillin. Sodium Borohydride Reduction of Vanillin: A Low Solvent - Sciencemadness %PDF-1.6 % In part 1 you will reduce 9-fluorenone using the procedure described below. search.ebscohost.com/login?direct=true&db=edsbl&AN=RN281558709&site=eds-live. 7-1! 4 0 obj fibrous layer 91 0 obj <> endobj Further information on the various types of reduction reactions and their mechanisms will be discussed in class. xq)nS* B(.eY)K9/Iy!gFo>H#" tWTg"3#27?5;a<4coOSC>]vne1Gz8Kvy6~^~WvMg6/k~{nnsHy_M9zoni^8qD _i{@?vnWiR"zE}w9? j. change in lens shape to focus retinal image sources such as water, alcohols, and carboxylic acids, producing fire. b. Design a controlled experiment to determine whether earthworms are more attracted to perfume or to vinegar. (0 g) / (112 g/mol) = 0 mols i. The reaction used to synthesize vanillyl alcohol from vanillin involves the reduction of an aldehyde to form a primary alcohol, or the reduction of a ketone to form a secondary alcohol. The experiment did not go entirely as planned, namely in that our solution did not precipitate. g. site of sharpest vision ELN and your post -lab formal report. 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. 5 ~ 1 cm . Experiment 2 post lab report; Lab 4 borohydride reduction; Mercedes Izquierdo Orgo 2 Prelab 1; Expierment 3 lab report Thompson, Karla . a. Sodium borohydride (NABH4) will be used for this process Lab Report 1 - Sodium Borohydride Reduction of Vanillin Low Solvent We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. direct=true&db=edo&AN=ejs8836881&site=eds-live, 2 Shibley, I. O4tf^< ,L439t c. Calculate the theoretical yield d. Write up the procedure, including observations e . To reduce vanillin to form vanillyl alcohol and characterize the sample using HNMR and CNMR. Reaction StoichiometryHOIn practice, it is best to use a 50-100% excess of . Note! EXPERIMENT 7: Reduction of Carbonyl Compounds - Achiral and Chiral Reduction Relevant Sections in the text (Wade, 7th ed.) 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. 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. bxBTxOl{]jN %mlh'{n>wrY`sIQ;ceXDO hb``` 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,)/$;&1Cu:C\$7_Bj;n-{nuigYPKr7K#!fo Introduction: Determine the purity of the products in part 1 and 2, as well as the success of each reaction using TLC. obtain an IR & H NMR, Results: 1.055 grams of sodium borohydride was added was slowly added to . References: Ege, Chapter 10,12,13; Microscale Techniques. chem 142 lab report exper 1 - 1 Experiment 1: Sodium Borohydride Cross), Educational Research: Competencies for Analysis and Applications (Gay L. R.; Mills Geoffrey E.; Airasian Peter W.), Chemistry: The Central Science (Theodore E. Brown; H. Eugene H LeMay; Bruce E. Bursten; Catherine Murphy; Patrick Woodward), Civilization and its Discontents (Sigmund Freud), Organic Chemistry I Laboratory (CHEM 253). r4RJ3FU6`xqi$*8lBU[@PzB Apy 3YSJr 6y|; stream PDF Experiment 1: Preparation of Vanillyl Alcohol l. farsighted ^y&6761 SPI6HxigLf50W$ZCe<0,=B%7i\Z,p8xT0])~G2 pVH"FpVnvc: VWC"%|9^4g.^Dev0tjX,l2;6vXyeygIKyJ^[L^P_`Y Why should sodium borohydride not be exposed to air for a long time? 10. Soc. The NaBH4 and NaOH solution failed to precipitate significantly in the ice bath even after scratching the side of the flask multiple times. /Jwobm~=tMx:i.O LSN q1_^`h]>,HWMu>%eS * It would be great to convert this table to text. evaporate out the DCM and wait for ***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. m. sense of smell In organic chemistry reduction reaction is basically the addition of hydrogen, also called 3. 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). In this experiment, vanillin, will be treated with a reducing agent, sodium borohydride in ethanol to produce, vanillyl alcohol. 2. POm~izqRdEqwETBwr?ZW0 h\BObalY6tu|[-IA.|WCd`v_DeyP`[!*"~ "mC%< *o~>w[-n6SgS ! controlled) product due to the presence of the methyl group which can sterricaly hinder or Oxidation and Reduction Reactions in Organic. Characterize the starting materials and products of part 1 and 2 by m.p. How did the 2 reactions differ? State why we employ NaBH . 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 . Be sure to include all steps and protonations. b. temperature receptors In the Ice bath, add 50 mg of HCl). Why is 95 % ethanol used? In the next lab period, determine the mass and melting point of your product. Sodium borohydride (NABH4) will be used for this process, since it is a mild reducing agent and relativel. Therefore, the sodium borohydride reduction of the ketone, 9-fluorenone was performed to yield the secondary alcohol, 9-fluorenol. he most common sources of the hydride Nucleophile are lithium aluminum hydride (LiAlH4) and sodium borohydride (NaBH4). Therefore, the vacuum filtration produced little to no filtrate. Michael Daniel Each molecule of NaBH4 can reduce up to 4 carbonyl groups since it delivers 4 hydrides per NaBH4 molecule. << /Filter /FlateDecode /Length 9804 >> Three of the unknown aromatic ketones should produce liquid products after reduction. Journal of Chemical Information and +@ T+5-0dj@?5W (tExZjIU_&unS~/fhz q;Mtt?~#bAp ]eDT -'?q._&gO$H;7!U` qP}zn%Pdb,%c^f 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 The mechanism for a NaBH4 reduction is the same except methanol is the proton source used in the second step. Chemistry 2283g Experiment 7 - Carbonyl Reduction ! %PDF-1.3 0.98 grams of Camphor was dissolved in 15 mL of ethanol.