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 spectrum of A has M^+: 149 (intensity 37.1% of base peak) and M^+ + 1: 150 (intensity 4.2% of base peak). Other spectroscopic data for A and B are given below. Justify the structures you propose by assigning specific aspects o the data to the structures. Make sketches of the NMR spectra. (a) The IR spectrum for compound A shows two bands in the 3300-3500-cm_1 region. The broadband proton decoupled ^13 C NMR spectrum displayed the following signals (information 3 from the DEPT 13C spectra is given in parentheses with the 13C chemical shifts): ^13 C NMR: d 140 (C), 127.(C), 125 (CH), 118 (CH), 24 (CH2), 13 (CH3)
(b) The IR spectrum for compound B shows no bands in the 3300-3500-cm_1 region. The 4 broadband proton decoupled ^13 C NMR spectrum displayed the following signals (information from the DEPT 13C spectra is given in parentheses with the 13C chemical shifts): ^13 C NMR: d 147 (C), 129 (CH), 115 (CH), 111 (CH), 44 (CH2), 13 (CH3)