NMR prediction using ChemDoodle, NMR calculation with Gaussian, and hands-on data collection using a benchtop NMR spectrometer were explored to assess their synergistic capacity in teaching NMR to organic chemistry students. Nine molecules representing functional groups commonly encountered in undergraduate organic chemistry were selected. Spectra obtained using each of the three methods were incorporated into a laboratory exercise where students utilized all methods to learn about NMR. Our approach combines experimental work with both an approximation and theoretical calculation providing students with a more comprehensive understanding. Ultimately, students learned how to perform NMR spectroscopy and how different computational tools can approach the problem in fundamentally different ways as outlined below. Our qualitative analysis reveals that students engaged in higher order thinking skills and reported several benefits to their learning.