4 a.

Unknown # 1 1.10 mL 2 0.485 mL 3 1.25 mL 4 0.918 mL 5 1.15 mL 6 0.700 mL 7 1.11 mL 8 1.10 mL 9 0.898 mL 10 1.30 mL 11 0.918 mL 12 0.700 mL 13 1.11 mL 14 0.898 mL 15 1.10 mL 16 1.15 mL 17 1.25 mL 18 0.918 mL

) What bands will you look for in the IR spectrum to help you determine that the starting materials were consumed and the product was formed? Be specific and include expected cm-1 values.

b.) What signals will you look for in the 1H NMR spectrum to help you determine that the starting materials were consumed and the product was formed? Be specific and include expected ppm values.

c.) Describe what features in the IR and 1H NMR spectra will help you to determine what the unknown alcohol is. Be specific.

Reaction: OH H2SO4 (conc.), A + ROH OR + H20 H3C H3C 4-methyl benzoic acid unknown alcohol ester R-4-methyl benzoate LOD D 4000 9000 2000 1500 1000 SDO HAVENUMBERI-1 3 11 10 9 00 7 6 Co IN 4 3 2 IN 1 0 ppm Unknown #1 #2 #3 #4 #5 #6 #7 #8 #9 #10 #11 #12 #13 #14 #15 #16 #17 #18 Product obtained Predicted/literature MP ester (mg) ester C 490.24 27.83 324.37 5.75 602.25 86 483.67 17.04 464.94 34.55 362.58 16.86 426.12 27.83 486.72 38.28 462.13 27.7 501.23 48.59 464.88 17.04 368.24 16.86 400.96 27.83 410.53 27.7 483.65 38.28 462.82 34.55 600.32 86 476.81 17.04 Actual MP ester C 26.9-27.8 5.5-5.7 84-85.7 15.1-16.8 32.5-33.9 14.9-16.1 25.8-27.5 37.0-38.1 25.6-27.4 46.0-47.9 15.9-16.8 15.0-16.2 26.1-27.0 25.5-26.4 36.2-37.9 32.1-33.8 84.6-85.8 15.2-16.7 Reaction: OH H2SO4 (conc.), A + ROH OR + H20 H3C H3C 4-methyl benzoic acid unknown alcohol ester R-4-methyl benzoate LOD D 4000 9000 2000 1500 1000 SDO HAVENUMBERI-1 3 11 10 9 00 7 6 Co IN 4 3 2 IN 1 0 ppm Unknown #1 #2 #3 #4 #5 #6 #7 #8 #9 #10 #11 #12 #13 #14 #15 #16 #17 #18 Product obtained Predicted/literature MP ester (mg) ester C 490.24 27.83 324.37 5.75 602.25 86 483.67 17.04 464.94 34.55 362.58 16.86 426.12 27.83 486.72 38.28 462.13 27.7 501.23 48.59 464.88 17.04 368.24 16.86 400.96 27.83 410.53 27.7 483.65 38.28 462.82 34.55 600.32 86 476.81 17.04 Actual MP ester C 26.9-27.8 5.5-5.7 84-85.7 15.1-16.8 32.5-33.9 14.9-16.1 25.8-27.5 37.0-38.1 25.6-27.4 46.0-47.9 15.9-16.8 15.0-16.2 26.1-27.0 25.5-26.4 36.2-37.9 32.1-33.8 84.6-85.8 15.2-16.7