MT2 Key ochem - Name Kg TA CHE 118B Midterm 11 Closed Book...

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Unformatted text preview: Name Kg: TA CHE 118B Midterm 11 November 24, 2010 Closed Book and Notes Points: 1.(30)_____ 2.(15)_#__ 3.05)” 4.(15)______ 5.05) 6.(10) Total (100) ix) Problem 1 (30 points) Outline the series of steps you would use to carry out each of the synthetic transformations. (Supply all missing reagents. Mechanisms are not necessary!) a) from E) o u 0 /\/\ q \\/\/ Mzmv v19 KOH /\/ Problem 2 (15 points) Rationalize the regioselectivity observed in the following reaction using resonance structures. 0 OH 0 OH HONo2 H2804 NO ‘0 Lint/“Aw -. 2 o w Q H2504 m <96 C—A; “\(gw/LNOZ \ N00 ‘\ N02 is 6:“(NiMm‘N‘wP emoeim 5w\os¥\5m3fiod\ ado“ WC oiwse wife/mi \C/DZM ‘ux RAWWQ 3 ’WR (6 page“ _ Walk/E, g0V\ '- b 0&4 O W 21/0“ MONO: 3 \\ W‘MOZ \\/0M 0 0 / / N Z \ \\/ _/—‘7 7' M a fi / Highk / <9 / \k/ “W QOCMAO SmiqSSAi'mLoA £00 Wm) (Vie/5 4"?- Jmsé ~L/Ozyx )«Wofegete Wei-m Smb5¥jw¥wonis ' Problem 3 (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) CH 943 J A 3 i / + H| /\ if 03m ‘ 3N \ H3O A > L Ow S 90 MS y 00/ ,5 CH3 0 ;/ I! dig O b) O H NaBH4 MGM Br H20, gr c) N111 No2 Zn (Hg), HCI O 2 d) 0 NH N/ e) o /H is + PhaPCHz ——-—-———> ether Problem 4 (15 points) Provide a detailed stepwise mechanism for the following reaction. $03H 0 E; fl is + HONOH ———>H 6 + H20 “if, (8M 4 9% Problem 5 (15 points) Suggest a structure that is consistent with the molecular formula and spectroscopic properties given below: Formula IR cm-l 1H NMR Chemical shift Integral ratio C7H5C10 1700 (strong) 5 7.6 doublet 2 5 7.9 doublet 2 5 9.9 singlet 1 (De/693% (,nSM'war/rlbfl : I; :{L \700 cw: : WEDA>\ [trawl meta/3r (efiiockem‘glry: w/°\~),/\\l ' \ m U1 '\ i \ ‘ \//\(/\ Olly Par 5 HMO“ 83/63 1 amt/Niko 510ml; {1 Pairs 0‘: Eat/\UAW‘XV' ly ngems) Problem 6 (10 points) Illustrate the meaning of the following terms by drawing a structure, diagram, or reaction or by providing a short definition or equation. a) ring activating, ortho, para directing /, Q I- Q . g N a 2 b) Hfickel's rule qrnhl ‘H as Karol/or nOWJOO'qd‘lnS) ‘m 04 c/vci ) ‘ SW macho/M 0T6 Catt/WU; 3:09 “romajfi‘lLYfl/Xh'm iflmmez/A'WOW . QHOMO / OCWQKCQ Vho\¢w\or (to 3“ C WW ((2 : JAG/MO.) ‘ 4v HM Lg d)conrotatory _ (0(L0n5/3me3 ((3de “m, Same JBCQd-Son m an Q\€omcyo\ic Cam/Hon . a) Ofime j\ (7M / L=N / ’\/ ...
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