Diazonium salts provide a route to many classes of organic compounds and can be prepared from aromatic amines. Scheme 1 shows the formation of a diazonium salt (3.2) from benzylamine (3.1) in step 1. Diazonium salt (3.2) is then reacted with the reagents in step 2 to give compound A and then in step 3 to give compound B. Scheme 1 3 2 4 3 5. NH2 NaNO2/HCI 5 6 80 step 1 6 7 3.1 7 3.2 8 H*/H₂O A B step 2 step 3 1 N2*CI CuCN Note Each C atom is numbered in 3.1 and 3.2 from 2 to 8 and the C in the CuCN regent (step 2) is numbered as C1. a. (4 marks) Draw the structures of compound A and compound B including the numbering of each C atom as given in Scheme 1, for both compounds. b. i. (8 marks) 13C NMR data for compound A and compound B are given in Table 3.1. Assign each peak to non-equivalent or sets of carbon atoms using the numbering assigned to each structure. Indicate the multiplicities for each carbon. A copy of Table 3.1 for this question is available to download under the Assessment tab. ii. (6 marks) Figure 3.1 shows the infrared spectrum of both compounds being labelled as spectrum 1 and spectrum 2. Using the IR correlation charts, assign the most likely type of absorption mode of the main bands in each spectrum (you do not need to consider the peaks in the fingerprint region between 1000 - 1600 cm 1). Hence, assign spectrum 1 and spectrum 2 to their corresponding compound. Table 3.1 13C NMR data for compound A and Compound B. Compound A Compound B Peak shift: Carbon Multiplicity (s, 5/ppm number d, t, q) Peak shift: 5/ppm Carbon Multiplicity (s, number d, t, q) 32 112 118 41 127 128 127 129 146 133 149 1.0 spectrum 1 0.8 0.6 0.4 0.2 0.0 4000 3500 3000 2500 178 wavenumber/cm-1 2000 1500 1000 1.0 spectrum 2 0.8 0.6 0.4 0.2 0.0 3500 3000 2500 2000 1500 1000 wavenumber/cm-1