Chem 204 - Endterm Test Mr 3007 (4) 1) Write the expected structure ofthe product in the box and show the mechanism of formation, 9 Partial IR data: Strong band a8 1730 em” (8) 2) Are these in your gun? Let's find out. Fillin the boxes. ° Ho" ¢ . Pen(3) 3) The 'H NMR spectrum of compound A shows (in ppm): 9.3 (4, 1H), 2.0 (octet, 1H), 1.5 (d, 6H). Fully explain Ho (6) 4) Astudentis asked to make compound B from propene. Point out any errors you see. Write a better synthesis. 3 App ee ! (2) 5) Write the products ofthe reaction in the box. ANN, AE(6) 8) An unknown G (CsH0;)" is treated with NaBH. No reaction occurs." It is then heated with KOH (ag) to form two products D (CH.0) and E. Compound D when treated with PCC and then Ag(NH:) shows a silver mitror on the flask” Compound E has a 'H NMR spectrum which shows: 12 ppm (bs, 1H) and 7.3 ppm (m, SH)-* Write the structures of compounds C, D and E. Very briefly explain the data in the sentences which have an asterisk. ‘Compound © ‘Compound D Compound E (4) 7) Demonstrate the disconnection approach in the synthesis the target molecule. The starting materials are the ‘only source of carbon to make up your target molecule. Any other chemicals may be invoked. © ont = Om = Q ‘Starting Matesls (1) Bonus: Draw the structure of the notorious drug GHB.