Learning Group Problem Chp 9, problem 1.
1. Given the following information, elucidate thestructures of compounds A and B. Both compounds are soluble indilute aqueous HCl, and both have the same molecular formula. Themass spectra of A and B have M+ 149. Other spectroscopic data for Aand B are given below. Justify the structures you propose byassigning specific aspects of the data to the structures. Makesketches of the NMR spectra.
(a) The IR spectrum for compound A show two bands inthe 3300-3500 cm-1 region. the broadband protons decoupled 13C NMRspectrum displayed for the following signals:
A: 13C NMR: 140 (C), 127 (C), 125 (CH), 118 (CH), 24 (CH2), 13(CH3)
(b) The IR spectrum for compound A show no bands inthe 3300-3500 cm-1 region. the broadband protons decoupled 13C NMRspectrum displayed for the following signals:
B: 13C NMR: 147 (C), 129 (CH), 115 (CH), 111 (CH), 44 (CH2), 13(CH3)
