Question

Problem #23: When compound X (C,H,Br) is reacted with sodium cyanide (NaCN) forms compound Y (C,H,N). Compound Y, upon reduction with H over a Ni catalyst, yields compound Z (C,HIN. The 'H NMR spectrum of X gives two signals, a multiplet at δ = 7.3 ppm (5H) and a singlet at δ 4.25 ppm (2H). The 'H NMR spectrum of Y is similar to that of X in that it shows a multiplet at ö-7.3 ppm (5H) and a singlet at o -3.7 ppm (2H) The 1H NMR spectrum of Z is shown below. What are the structures of compounds X, Y and Z? TMS 3.0 2.5 8H (ppm) Problem #24: An unknown compound, A (C7H10), shows four absorptions in its 13C-NMR spectrum, at δ 22 (CH), 24 (CH), 124 (CH), and 126 (CH). On reaction with excess H2 and a Pt catalyst, A produces B (C,H4). B shows a single peak at 8 28.4 in its SC-NMR spectrum. Ozonolysis of A gives C,H,O, and C,H,O2. Suggest structures for A and B. Problem #25: The product of the acid-catalyzed hydration of 3- methyl-1-butene has a broad absorption at 3330 cm in its IR spectrum. Its 1C proton-coupled NMR spectrum shows absorptions at o 70 (s), 34 (t), 30 (q), and 15 (q). Suggest a structure for this compound.

Answer 1