Question

Some one please help me with this question :) Make sketches of the NMR spectra.

Given the following information, elucidate the structures of compounds A and B. Both compounds are soluble in dilute aqueous HCl, and both have the same molecular formula. The mass spectra of A and B have M+ 149. Other spectroscopic data for A and B are given below. Justify the structures you propose by assigning specific aspects of the data to the structures. Make sketches of the NMR spectra.

(a) The IR spectrum for compound A show two bands in the 3300-3500 cm-1 region. the broadband protons decoupled 13C NMR spectrum 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 in the 3300-3500 cm-1 region. the broadband protons decoupled 13C NMR spectrum displayed for the following signals: B: 13C NMR: 147 (C), 129 (CH), 115 (CH), 111 (CH), 44 (CH2), 13 (CH3)