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Fischer Esterification
What is the experimental and theoretical percent yield?
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- The mechanism of the Fischer esterification was controversial until 1938, when IrvingRoberts and Harold Urey of Columbia University used isotopic labeling to follow thealcohol oxygen atom through the reaction. A catalytic amount of sulfuric acid was addedto a mixture of 1 mole of acetic acid and 1 mole of special methanol containing the heavy18O isotope of oxygen. After a short period, the acid was neutralized to stop the reaction,and the components of the mixture were separated.H2SO4OCH3 C O H CH3 O H CH3 C O CH3 H2OO18 + +(a) Propose a mechanism for this reaction.(b) Follow the labeled 18O atom through your mechanism, and show where it is found inthe products.(c) The 18O isotope is not radioactive. Suggest how you could experimentally determinethe amounts of 18O in the separated components of the mixtureCalculate the theoretical yield of virstatin ethyl ester and virstatin. Procedure – Step 1 Synthesis of virstatin ethyl ester (with notes and musings about procedural steps in italics) 1,8-naphthalimide (0.25 g) and potassium carbonate (0.26g) are added to a 10 ml round bottom flask containing a stir bar. 1.3 ml DMF (N,N-dimethylformamide) is added to the flask. The DMF will be in a “sure seal” bottle with a septum. You will obtain the DMF using a syringe and needle. Wear gloves when obtaining and dispensing the DMF. Add ethyl 4-bromobutanoate (0.27 ml) (it might say ethyl 4-bromobutyrate on the bottle) to the reaction flask, using an automatic pipet. Heat under reflux, with stirring, for 1 hour. What will the sand temperature have to be to get DMF to boil?? When would you start heating the sand!? After cooling to room temperature add 5 ml water to the reaction solution and cool the resulting mixture in an ice bath. Using a Buchner funnel, vacuum filter the ice cold…A student was trying to treat an alcohol with PCC and when they took the IR below they wanted to see if the product had formed. What evidence supports the suspicions that the product did form?
- Synthesis of p-Bromoaniline The student observes a melting point of 110-113 C for the acetanilide. The literature melting point is 114 C. Which conclusion can he draw from these observations? (Check all that apply) a) The compound has 98 % purity. b) The sample is still wet. c) The solid is impure. d) The isolated compound in the target compound.Add L-Alanine to a solution of 2M NaOH and then add this to a solution of di-tert-butyl dicarbonate in MeOH in a small conical flask. Stir the mixture at room temperature for 30 min. A white precipitate should be observed. What is the role of NaOH? An Rf is given for the product, how will it change if the eluent mixture was more polar? Draw the curly arrow reaction mechanism to show bonds being formed/broken.Multistep synthesis of Lidocaine Lab 1) How many grams of starting material do you need? It is given in moles below but how many grams? 2) How to calculate theoretical yield? Part One Method A. Preparation of alpha-Chloro-2,6-dimethylacetanilideCombine 0.033 mol of 2,6-dimethylaniline with 25 mL of glacial acetic acid (or ethyl acetateor THF) and 0.033 mol of alpha-chloroacetyl chloride, in that order, in an appropriately sized Erlenmeyer flask. With the aid of a hot water bath, warm the solution to 40-50°C, remove the flask from the bath, and add a solution of 5 g of sodium acetate trihydrate dissolved in 100 mL of water.
- Describe how the product is purified. 4,4'-DIBROMOBIPHENYL [Biphenyl, 4,4'-dibromo-] Submitted by Robert E. Buckles and Norris G. Wheeler1. Checked by R. S. Schreiber, Wm. Bradley Reid, Jr., and Robert W. Jackson. 1. Procedure In a 15-cm. evaporating dish is placed 15.4 g. (0.10 mole) of finely powdered biphenyl (Note 1). The dish is set on a porcelain rack in a 30-cm. desiccator with a 10-cm. evaporating dish under the rack containing 39 g. (12 ml., 0.24 mole) of bromine. The desiccator is closed, but a very small opening is provided for the escape of hydrogen bromide (Note 2). The biphenyl is left in contact with the bromine vapor for 8 hours (or overnight). The orange solid is then removed from the desiccator and allowed to stand in the air under a hood for at least 4 hours (Note 3). At this point, the product weighs about 30 g. and has a melting point in the neighborhood of 152°. The crude 4,4'-dibromobiphenyl is dissolved in 75 ml. of benzene, filtered, and cooled to 15°. The…Write R if the compound will give positive result to chromic acid test and S if not. 1. 2. 3. 4. 5.10. Show the step-by-step process. Do not use shortcut methods. Make it as detailed as it can be. ENCODE (not hand-written)!
- Results and Discussion: Nitroprusside Reaction: Samples: cysteine, cystine, glycine Reagents: Saturated Sodium Carbonate (Na2CO3) solution, Saturated Sodium Nitroprusside solution, 1.0% sodium cyanide (NaCN) -To 0.5 ml of the sample, add 0. 25 ml of saturated sodium carbonate solution and a drop of freshly prepared saturated solution of sodium nitroprusside (HANDLE WITH CARE). A purple color will develop if free sulfhydryl groups are present. If negative, add 1 drop of 1.0% NaCN. The development of a red color indicated the presence of disulphide bonds.Why is it important to thoroughly vortex the contents of the vial after adding reagent 4 (Steps 3 and 4., stage 1). To ensure that the two immiscible solvents come into contact with each other, permitting the derivatization reactions to occur. B.To ensure that the solution is mixed thoroughly. To ensure that all the amino acids are transferred to the lower aqueous layer so that a full extraction occurs. To remove all the interferring compounds by transferring them to the upper organic layer Hint: Reagent 4 is the derivatizing agent dissolved in octane.What impurity was likely removed during the recrystallization necessary and was it effective and why do you think so using the prcedure belwo and the reaction provided. PROCEDURE Synthesis of Dibenzalacetone (A) In this lab you will need to determine the amounts of the reactants you will use. We will use 0.0125 moles of acetone. You need to: (1) convert this into a volume in mL, (2) Calculate the number of moles of benzaldehyde needed based on the balanced chemical reaction, (3) Convert the number of moles of benzaldehyde into volume in mL. Your reagent table should reflect your calculated values. Mix the benzaldehyde and acetone based on the volumes from your prelab calculations in a testtube. Add 25 mL of 10% NaOH solution to a 125 mL Erlenmeyer flask along with a stir bar and 20 mL of ethanol. Make sure the temperature of the solution in the flask is below 25 C before proceeding. Add half of the solution from your test tube to the flask. Allow the solution to…