Question

NMR IR Post-Lab Questions Name: Elizabeth Bean HWI. A student ran the following reaction 1 equiv. Nah then MeBr HC A TLC or the reaction after workup indicated the presence of TWO spots. After running a column and separating the two compounds by TLC, the student found that the majority of the mass gave the following NMR and FT-IR data. Is the majority of the yield the desired product? Explain your answer. (HINT, compare the spreetra below with those of P7 and P8. What signals are most diagnostic for your product vs. starting material in both IR and NMR?) transmittance Wavenumber cm

Answer 1

Student performed the reaction and obtained two spots. He is isolated major spot. The major spot is the reactant. But not the product. If it is product it should have shown the peak for newly added methyl group. In this NMR, No methyl signal is present.

NMR and IR Post-Lab Questions Name: Elizabeth Bean HWI. A student ran the following reaction 1 equiv. NaH then MeBr HC-o но A TLC of the reaction after workup indicated the presence of TWO spots. After runninga column and separating the two compounds by TLC, the student found that the majority of the mass gave the following NMR and FT-IR data. Is the majority of the yield the desired product? Explain your answer. (HINT: compare the sprectra below with those of P7 and P8. What signals are most diagnostic for your product vs. starting material in both IR and NMR?) 100 C-H stretching O-H stretching 3000 2600 2400 1800 Wavenumber cm Tertiary butyl group NO methyl signal in this region Aroamtic ring protons ppm transmittance ()

Он 4-(tert-butyl)phenol ChemNMR 1H Estimation 1.33 1.33 1.33 7.37 7.37 6.60 6.60 OH 9.06 2 10 6 0 PPM Me 1-(tert-butyl)-4-methoxybenzene ChemNMR 1H Estimation 1.33 1.33 1.33 7,54 7.54 6.78 6.78 3.81 T 4 7 6 3 2 0 PPM