Name - ow TA, CHE 118C Midterm I October 22, 2013 Closed Book and Notes Points: 1.20) 2.12)__ 3.(20)__ 41) 5.15) 6.21). Total (100).Problem 1 (20 points) Suggest a chemical structure that is consistent with the molecular formula and spectroscopic properties given below: Formula 8 NMR ('H uncoupled) ‘HNMR Chemical shift . CHO. 9170, 52,20 16 8.13 tiplet 3 82.6 singlet 2 84.2 quartet 2: 2te)r2 ® :) - © 5) C-NMR; § 170 = canberyf cauben = —cH,~ ui) § 4% = methyl = . iS yee = cH, - @ u only FP Aydncgn neconsted » aot ioe, Frese Le jderticc! ah i) gn32 -ch-cHy Myr §2,67 Ot y unsat. = UASay = reels SUL > Zc ty a, ——% FOnsty @Q otk Ao °Problem 2 (12 points) In each of the following pairs, which is less basic? Give a brief explanation. ee @ i? hy ( ® Nip /NHe py) eee QProblem 3 (20 points) Write a step-wise mechanism for the following reaction.Problem 4 (12 points) Provide the reagents necessary to carryout the following transformations: a) _ b) °) d) arr Lath 4 ar ° ) Me MgB 9 CN Oo 4) Heo8 Problem 5 (15 points) Predict the products for each of the following reactions. Note: You only need to show the final products to receive full credit. a) Woy Nats UAH, NaoH a He ether HO T Su, c zB Vy b) e 1, AAoy Noe Uw oH A °) 9 MaBr - On. Or 1. (excess) "= a) a” CHsI (excess) Ago KxCOs H,0 a e) 4) HCL + CHO + (CHy,NH DHOOProblem 6 (21 points) Provide the necessary reagents to carry out the following synthetic transformations: (Note: More than one step will be necessary!) a) er N Ov 3 OF es + i 2 NaOH, 4,0 ? 3) aw. 4 a PB yy CH, ) PBr, (25 ls aa - ves nay? 2) NH3 ceveess) ° 9° \soch, 3. 5 & pe; 4 ght NM oe oi ) sedian ne ES, ceo add