Given the following information, elucidate the structures of compounds A and B. Both

Chapter 9, Problem 1

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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+ D 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 shows two bands in the 33003500-cm-1 region. The broadband proton-decoupled 13C NMR spectrum displayed the following signals (information from the DEPT 13C spectra is given in parentheses with the 13C chemical shifts): 13C 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 33003500-cm-1 region. The broadband proton-decoupled 13C NMR spectrum displayed the following signals (information from the DEPT 13C spectra is given in parentheses with the 13C chemical shifts): 13C NMR: d 147 (C), 129 (CH), 115 (CH), 111 (CH), 44 (CH2), 13 (CH3)