Flowchart, purification, and characterization Provide a flowchart for the workup
ID: 543692 • Letter: F
Question
Flowchart, purification, and characterization Provide a flowchart for the workup for the reaction below. How would you purify this reaction (be specific and state why)? The yield for the reaction is 90% List the key peaks (give proton/functional group type and the expected shift/frequency for each peak you list) in the NMR and IR spectrum that would help you differentiate the product from the reactant NaOCI, TBAB CH2Cl2, H20 OH BP = 280 °C BP = 250 °C TBAB = tetrabutyl ammonium bromide, an ionic catalyst Flowchart and purification Provide a flowchart for the workup for the reaction below. Would you be able to use recrystallization or distillation to purify this reaction? Whylwhy not? The yield for the reaction is 70% OH OH MP = 70 °C MP = 60 °CExplanation / Answer
After the specified/optimized reaction time, the reaction can be quenched using distilled water to get rid of the salts present in the reaction mixture. Then the crude compound can be extracted thrice using calculated quantities of dichloromethane. All the three combined extracts of dichloromethane should be dried over Na2SO4 to absorb traces of moisture present in the organic layer, followed by filtration to another flask to obtain the moisture-free crude compound.
The above compound can be purified using silica-gel column chromatography by choosing the appropriate eluent mixture of hexane/ethyl acetate.
The pure compound can be characterized using various spectroscopic techniques like IR, NMR, etc.
1H NMR: The product has aldehyde group, corresponding aldehydic proton appears at ~9.7 ppm, whereas the reactant has an alcohol group, corresponding alcohol proton appears at ~5.0 ppm.
13C NMR: The product has aldehyde group, corresponding aldehydic carbon appears at ~194 ppm, whereas the reactant has an alcohol group, corresponding alcohol attached carbon appears at ~63 ppm.
IR: The product has alpha,beta-unsaturated aldehyde group, corresponding CO stretching absorption occurs at ~1700 cm-1, whereas the reactant has an alcohol group, corresponding O-H absorption occurs at ~3400 cm-1.
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