Goals Synthesize a new salen complex (eq 2 ), and obtain a H NMR spectra Synthesize the corresponding Mn(salen) complex (eq 3) Compare isolated yields of the catalyst with your labmates Epoxidize stilbene using the published Jacobsen procedure and your catalyst(eq 4) Determine the conversion of your reaction using H NMR analysi Purify your crude reaction mixture by flash column chromatography, and obtain a yield. Obtain a HNMR spectrum of the pure epoxidation product. Compare conversions and isolated yields with your labmates. Use your results to make predictions about the correlation between catalyst structure and catalyst efficiency. This will help us to plan better catalysts in the future Hints from your graduate student mentor: 1. Making the Salen ligand (eq 2) Reactions that you shouldnt try: (I had problems making the Mn(salen) complex with these ligands. 1)ethylenediamine salicylaldehyde 2)trans-diaminocyclohexane +3, 5-di-tert-butyl, 2-hydroxybenzaldehyde 3)ethylenediamine nitrosalicylaldehyde 4)ethylenediamine chlorosalicylaldehyde You should aim to make 1.00 g of the Mn(salen)complex. Do your calculations based on the two reactions proceeding in 70%o overall yield Don't forget that after the reaction finishes you ll need to add water to precipitate therate There will be a large amount of solid produced, so use a large stir bar and fast stirring product, so dont start with too small a reaction flask When you first isolate the ligands(and later the metal complexes), they will be very wet, so dry them overnight in your desiccator before you determine their weight Note the difference between ethanol and absolute ethanolGoals: • Synthesize a new salen complex (eq 2), and obtain a 1 H NMR spectra. • Synthesize the corresponding Mn(salen) complex (eq 3). • Compare isolated yields of the catalyst with your labmates. • Epoxidize stilbene using the published Jacobsen procedure and your catalyst (eq 4). • Determine the conversion of your reaction using 1 H NMR analysis. • Purify your crude reaction mixture by flash column chromatography, and obtain a yield. • Obtain a 1 H NMR spectrum of the pure epoxidation product. • Compare conversions and isolated yields with your labmates. • Use your results to make predictions about the correlation between catalyst structure and catalyst efficiency. This will help us to plan better catalysts in the future. Hints from Your Graduate Student Mentor: 1. Making the Salen Ligand (eq 2) • Reactions that you shouldn't try: (I had problems making the Mn(salen) complex with these ligands.) 1) ethylenediamine + salicylaldehyde 2) trans-diaminocyclohexane + 3,5-di-tert-butyl, 2-hydroxybenzaldehyde 3) ethylenediamine + nitrosalicylaldehyde 4) ethylenediamine + chlorosalicylaldehyde • You should aim to make 1.00 g of the Mn(salen) complex. Do your calculations based on the two reactions proceeding in 70% overall yield. • There will be a large amount of solid produced, so use a large stir bar and fast stirring rate. • Don't forget that after the reaction finishes you'll need to add water to precipitate the product, so don't start with too small a reaction flask. • When you first isolate the ligands (and later the metal complexes), they will be very wet, so dry them overnight in your desiccator before you determine their weight. • Note the difference between ethanol and absolute ethanol. 38