:CI: B (a) NO NO You wish to prepare various isomers of chloronitrobenzene from benzene. For simplicity, they have been labeled A, B and C: :CI: (c) . A B Consider how 'H NMR can be used to identify which product(s) are made from each reaction. For each isomer, complete the table provided to clearly indicate: The relative integration of each peak The multiplicity of each peak if no long range coupling is observed If each peak could reasonably be expected to experience long range coupling. Isomer A Peak If long range coupling is expected, write the number for the proton(s) coupled to. If long range coupling is not expected, write "N/A" or leave the last box blank. Isomer A has been numbered for you. Please number Isomers B and C on the pictures next to each table. Use one number for each peak expected on the H NMR. 1 4 NO Isomer B Isomer C Peak Integration Peak Integration Integration NO Multiplicity Multiplicity Multiplicity [17 marks] :CI: Might have long range coupling? (yes/no) Might have long range coupling? (yes/no) Might have long range coupling? (yes/no) Long range coupling is with which proton(s)? Long range coupling is with which proton(s)? Long range coupling is with which proton(s)? (b) If you wish to prepare Isomer B (as the major product), what sequence of reactions should you use? [3 marks] : CI: B If you wish to prepare Isomer C (as the major product), what sequence of reactions should you use? [3 marks] :CI: NO C (d) Preparing Isomer A as the major product is a more difficult task. Even in the industrial process used to make it commercially, it's only a minor product (-35% Isomer A; -65% something else). Why? [2 marks] : CI: NO NO