ORGANIC CHEMISTRY Nae SPRING 2012, LANEY COLLEGE Chew ae itil) INSTRUCTOR: 8, CORLETT Evan 3 Practice Page 2of 8 1. Define the following terms (15 points) a benzylic ae bentyl covfen rol — ~ sp8 carton clrectl, oe Mtaclad to an meraths ns any pubsttissut om cur aromdtie nrg hot teeter He rots of theertraphile ownetee autetbuhen rslave 1 hougow , ©. benzyne 4. conrototory a —» (5 points) Solid cinnamie acid when left in direct sunlight for several days undergoes a photochemical reaction to yield two products, truxillic and truxinic acid. What are the structures of these products (including stereochemistry) and how are they formed (what type of reaction)? (10 points) S Thay te ‘ O00 damien both predudh ave trem C2423 : poke cLowiced odelibor, GedORGANIC CHEMISTRY SPRING 2012, LANEY COLLEGE CHEM 128 LULIL) INSTRUCTOR: 8. CORLETT Exam 3 Practice Page 3 of 8 4. Provide IUPAC names (not common) for the following aromatic compounds (10 points) NH NO, a b. OCH; i egg grit Unnitis oars . or (1-mrethyhatay? ¢ ae ma! Sellar sale (merlaghathy? ) amaleno ot 5. Draw the structure of the following compounds. (0 paints) &. _24methoxymethyl)-3-nitrobenzenesulfonie acid OH; 4 1 Sos or b.-2-bromophenol oH aR eT 6. Foreach ofthe following molecules or ions indicate whether they are aromatic, anti-aromatic or non= aromatic (16 points) o O oxazole Pentalene _cyclopemtadiene _cycloheptatrienyl cation Pn ae ba = Drom tie anowsle — oramaligORGANIC CHEMISTRY (CHEM 128 (LULIL) Exam 3 Practice SPRING 2012, LANEY COLLEGE INSTRUCTOR: S. CORLETT Page 4 0f8 7. Show the product (or products) and the complete mechanism (with electron-pushing) for the following reaction. (if more than one isomer is formed show the mechanism for only one of them, but be sure to show all expected products) (Hint: you must show how FeBr3 is involved in the mechanism) (15 points) Bry oe FeBry . a Ss eee Cr : \ |B. aes He - icant oe DeORGANIC CHEMISTRY (CHEM 128 (LULIL) Exam 3 Practice SPRING 2012, LANEY COLLEGE. INSTRUCTOR: S. CORLETT. 8. In the following synthesis, fill in the products or reagents. There may be more than one step required for transformation and there may be more than one product produced in a given step. (25 points) No. Hos ore | _zottio aN g | AR 7, Wzor . 3 cs a AN ey ch Sey Qi OT ae : D SNS ay i aT . : Side product ~ 2oerky 4 9, (5 points)ORGANIC CHEMISTRY ‘SPRING 2012, LANEY COLLEGE (CHEM 128 (LULIL) INSTRUCTOR: S. CORLETT. Exam 3 Practice Page 6 of 8 10. Another method to generate a benzyne is from the o-bromofluorobenzene and magnesium. Show the product from the following reaction. (5 points) EXTRA CREDIT Show the mechanism of this reaction (10 EC points) CO ag, YS ore SF 11. Phenanthrene, is officially aromatic, but is more reactive than benzene toward bromine. Also it reacts with bromine (without a catalyst) to give a single dibromide product. Suggest the structure for the dibromide product and suggest a reason why only reacts in one location. + Ss (10 points) \ ott HY cromebie parities dow Leal 7 repORGANIC CHEM CHEM 128 (LL Exam 3 Practice B TRY SPRING 2012, LANEY COLLEGE. INSTRUCTOR: S. CORLETT Page 7 of 8 Use the included NMR data (on p. 8) to estimate the 'H NMR chemical shift of the aromatic hydrogens for aniline and the anilinium ion, For each structure explain how the NMR data indicate whether the substituent on the aromatic ring is an orthorpara director or a meta director in the Electrophilic Aromatic Substitution reaction. (use the values for NMey+ I for N+) and whether the ring is actived or deactived. (1S points) Given your answer to the above question, what product should be produced when aniline is subjected to the conditions for nitration (HNOs, H»SO,)? points) “a Me a Sn oni El, * ry ae SA no, hey ASO a~50%