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(Solved): Q6. 1. The proton -decoupled 13C NMR of A(C_(6)H_(3)Br_(3)) showed only two signals. What is the ele ...



Q6. 1. The proton -decoupled 13C NMR of A(C_(6)H_(3)Br_(3)) showed only two signals. What is the element of unsaturation? Draw the structure of A . (5) Given the following information, elucidate the structures of compound A . The compound is soluble in dilute aqueous HCl . The mass spectrum of A has M+:149. Other spectroscopic data for A is given below. Justify the structures you propose by assigning specific aspects of the data to the structures. (5) 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 from the DEPT 13C spectra is given in parentheses with the 13C chemical shifts): ^(13) C NMR: ppm; 140(C),127(C),125(CH),118(CH),24(CH2),13(CH3) Two compounds with the molecular formula C_(5)H_(10)O have the following ^(1)H and ^(13)C NMR data. Both compounds have a strong IR absorption band in the 1710-1740-cm_(1) region. Elucidate the structure of these two compounds and interpret the spectra. (10) (a) ^(1) H NMR: d 2.55 (septet, 1H), 2.10 (singlet, 3H), 1.05 (doublet, 6H); ^(13) C NMR: d 212.6, 41.5, 27.2, 17.8 (b) 1H NMR: d 2.38 (triplet, 2H), 2.10 (singlet, 3H), 1.57 (sextet, 2H), 0.88 (triplet, 3H); 13C NMR: d 209.0, 45.5, 29.5, 17.0, 13.2


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