Q3 Lab#3 Amide DEET FINAL.docx

Removed leaving a cloudy yellow mixture that was

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removed, leaving a cloudy yellow mixture that was dried with sodium sulfate, decanted, and dried with nitrogen gas. The resulting yellow oil product was purified through small-scale chromatography (with hexane) and dried with nitrogen gas. Name m-toluic acid Thionyl Chloride Diethylamine Ether N,N-diethyl-m- toluamide Formula C 8 H 8 O 2 SOCl 2 C 4 H 11 N C 4 H 20 O C 12 H 17 NO Molecular Weight 136.148 g/mol 18.97 g/mol 73.14 g/mol 74.11 g/mol 191.29 g/mol Quantity (g, mL) 0.272 g 325  µ L 660  µ L 1.33 mL 0.383 g Millimoles 2.00 mmol 4.47 mmol 6.38 mmol 12.80 mmol 2.00 mmol Equivalents 1.00 2.24 3.19 6.40 1.00 Density/mass % 1.05 g/ml 1.64 g/ml 0.71 g/ml 0.71 g/ml 0.99 g/ml MP/BP 111-113 ° C -104.5 ° C -50 ° C -116.3 ° C -33 ° C
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Results Product:  Crude Yield (mass, %) 0.216g, 56.4% Final Yield (mass, %) 0.079g, 20.6% Description (state, color) Thick, yellow liquid NMR sample (solvent) CDCl 3 1 H NMR 1H NMR (400 MHz, CDCl3) 7.17 (br m, 7.28-7.10, 4H, b, c, d ), 3.52 (br s, 2H, e ), 3.23 (br s, 2H, e* ), 2.34 (s, 3H, a ), 1.22 (br s, 3H, f ), 1.09 (br s, 3H, f* ) [* denotes the non- specificity in labeling the ethyl groups – Dr. Nelson] FT IR (diamond anvil, neat) 2915.47, 2847.94 cm-1(sp3 C-H stretch), 1633.32 cm-1 (C=O stretch, amide), 1219.91 cm-1 (C-N stretch) Discussion  
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