Experiment #10: IMINE / INDOLE REACTION A. Data (Show all calculations) Ketone Used Cyclopentane Mass and moles of keton

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: Experiment 10 Imine Indole Reaction A Data Show All Calculations Ketone Used Cyclopentane Mass And Moles Of Keton 1 (30.54 KiB) Viewed 44 times

: Experiment 10 Imine Indole Reaction A Data Show All Calculations Ketone Used Cyclopentane Mass And Moles Of Keton 2 (42.07 KiB) Viewed 44 times

: Experiment 10 Imine Indole Reaction A Data Show All Calculations Ketone Used Cyclopentane Mass And Moles Of Keton 3 (28.43 KiB) Viewed 44 times

Experiment #10: IMINE / INDOLE REACTION A. Data (Show all calculations) Ketone Used Cyclopentane Mass and moles of ketone actually used 1.15ml, .0129 moi, 1.089 a 115.947. 1689 = .0129 19 84-12 gimo Mass and moles of phenylhydrazine hydrochloride actually used: 4354,-0030 bol .435 mol 144.60g Volume and moles of acetic acid actually used: 1.049 mig goble moi - 01665 10.05 Zgimai Theoretical Yield calculations Hydrazone: 0030 moi * 12.4.24 gimol = .5249 Phenyl hy crazone Phenyi nyonezve limiting Indole: .0030 x 157.21 g/mol = 1.471634 T indole limiting
Heating method used 2 (50 seconds) Mass of product isolated .IS quam MP of product isolated 100-1030 Identity of product isolated (draw structure) Percent Yield of Product B. Analysis. Attach the IR spectra of your starting material and product along with a table listing all major IR absorption bands (you must label the bond, motion, exact functional group and position for the absorption, for example: O-H stretch of a 2" alcohol at wax cm) TLC. Draw the TLC plate below, marking start and stop lines Identify each spot, show distances (measured in mm), and calculate Rf values for starting material and product(s) Sample Questions • Draw an extraction flowchart showing a) the 5 major organic compounds which could be found in the crude product mixture, b) what happens to cach of these species after the water extraction, HCI extraction, and NaCl extraction. • What is the purpose of the sodium chloride extraction? • Would distillation be a good way to separate a mixture of these two compounds? Why or why not? • What is the driving force which might cause the isolated product to form in preference to the other possible product? • Which of the microwave heating modes are being utilized during this reaction? • What is really happening to the power when it is set to "10%? • What are the advantages and disadvantages to each of the two heating methods which might be used in this synthesis? • How would you use 'H NMR to differentiate between the two products? • If a TLC had been run on the reaction mixture after heating (using an appropriate eluent), how would it have looked? Draw a quick sketch
80 1724.48 3050.43 70 60 12900.58 1368.30 2858.08 2945.21 OE 50 1192.35 842.47 1086.85 919.00 1008.77 1120.75 Stretch 1617.95801 Cyclopenting 1312.86,290,041272.13.237.84, 584.57574.86 40 338376 C-H Stretch Sp 1444.89 % Transmittance 627.10 486.94 30 N-Streen Qucohol 20 10 733.83 444.34 0 -10 434.64 424.72 413.37402.63 -20 4000 3500 3000 1500 1000 500 2500 2000 Wavenumbers (cm-1)