zimm-exam2a-Spr05

zimm-exam2a-Spr05 - o #12»- Organic Chemistry 345 Name...

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Unformatted text preview: o #12»- Organic Chemistry 345 Name (Please Write Clearly) Spring 2005 Exam 2a ___{£5;1______ Student ID Home Street Name (as in UW Records) Your Seat Number Question Points Grader’s Initials 1 L— 2 2° ‘fcs 10 11 V‘V‘WV‘N‘WHwi? 12 My — flux pup/M £700 (2 Points for each Synthetic Question and 5 Points for each Mechanism Question) Page 8 to be used for Scratch P92 Organic Chemistry 345 Spring 2005 Exam 2a Name (Please Write Clearly) 1. Give the products of synthesis as isolated after workup. ’ MQ. ' c)‘ d) f) h) PhCEN Cumene Hydroperoxide O + Me—l A H3P02 LiAIH4, Et20 Dil. sto4 m . S Me D-Mannose Acetophenone' + Me2NH+- CH2=O D-Gulose Ph-C-CHz-C-CH3 II o N Ill N+ N Me S Y CI' 1) BuLi 2) Benzyl Bromide pk “Qt CHLUHpfl re re- PQ\MQ. f1 Mfaapk -————> HCN, NaCN 2 KNH2 Liq NHs Benzyl Bromide II o —.._—> CuCN —-——> Dil. HNO3 .E Ml QM 1 *- gram CDOH: PLW'OFCRC 0 E32 9/ W‘roH i- MeLc: b 1’vr&:‘f HC' rk géacuL‘cm-umz, 9—CHL‘GH1'PLL (S i I__" Gwyn 0M {0 c , uf/fifwljhgbfiwfi) Pg3 Organic Chemistry 345 Spring 2005 Exam 2a _K:L___ Name (Please Write Clearly) 2. Give the products of synthesis as isolated aft rku 7/6” ) a) O . é Pyrrolidine, TsOH K Benzene distillation CH; 914 W914 b) D-Threose ——> H‘ 1. @000“ 1. HONO b C) NH2 2. Furan A 4 \ ll H d) NHCCH3 N 2, ' ___.__. 7 Dil HCI, A bum“ SOZNHZ v ' e) bBuWI . " s —_.—_. ' / - 4“ Q” UHV KNH2, Liq. NH3 A} H], C E) Ph—fi—NHZ Br2, NaOH ’0 )1’6/(‘11‘ O -cvoE Ph-N=C=O + EtOH [PL— Nfl ,5, f g) - , . QobH, - ————> h) D Erythrose Brz H20 0(4 . v A i) Benzoqumone ———> UNI; SUC12 o H. a 3') Ph-C=O \ . PL'C HI.” “I NEt2 LIAIH4’ Et20 QL Pg4 Organic Chemistry 345 Spring 2005 Exam 2b v Name (Please Write Clearly) 3. Give the products of synthesis as isolated after Workup Coon— a) D—Ribose ———» Dil. HNO3 cent-k O F0 1 KOH b) NH ) / \ KN—Me, 2) Methyl Iodide ‘/ O o ) F s 1 a c I m-Cresol M , ‘ ' i.e. (K803)2N=O m) ‘ 0 M d) |e _ Ph-C-CH-S-Me (crack 'Mb || || AKHQ) W n 1 o o o e) 0“ » + Dil. Sulfuric Acid A / f ) H+ ‘ Cyclohexanone + 1,3—propanedithiol _> V \— M N N @N 2:.“ o N £3, + N,N-Dimethylaniline \— J ' <>© SO2C| + Diethylamine —> @801-N9t1 0H OMe HI O 4' M271 Mb 0 1.Ben2yl Bromide 0M1?“ 2. H20 workup Organic Chemistry 345 Spring 2005 00 5Q Pg5 $00 5 Name (PleZse Write Clearly) 4. For each of the following put in the reagent(s) (over the reaction arrow) needed to give the indicated product. Exam 22 a) 9 NH HN—C-NH-Ph 62 TLC” G b) o’CH3 0’” :5 L A i) _OH OH C) [ij Efirs or Esrzfacmarij 0 Br “a... d NH o e HN’ ' 3 ’ . 2 mac») . or Grade: 5. Which is more acidic, phenol or p-benzoylphenol? {3—Way phenol Now draw the most important resonance structure acco nting r this difference. 7 PM ' .'__ —— / .p—Qma ® 1029 6.Draw the mechanism of the Claisen Rearrangement of allylphenol. Give the final product as well as any reaction intermediates. As usual, put in all charges, unshared electrons and arrows neatly drawn. (Note that the terminal carbon is isotopic). CH\ * H 0’ \CH2 CD 0.) \ Q9 1\ 0“ €30 “CW-L \l 9! 2 \ / ¥ // web WW9 1/ Pg 6 Organic Chemistry 345 Spring 2005 Exam 2a k/ 67 Name (Please Write Clearly) 7. Which is more basic, p-methoxyaniline or p-cyanoaniline? P” mefl’wx‘l 3”“ I'M IX ' (Answer) . Now draw the most importanEBresonance structure accounting for this difference. H,¢“’H .‘Z L? -’.(9 8. How are Erythrose add Threose related? They are DIESfLMVVMQQS (Enantiomers, Diastereomers, Geometric Isomers, None of these). 9..Using the framework drawing A, put in the groups necessary to give a-D-galactopyranose. ,’~——’—“ g: ,fiq AD OH QHin' AL OH 10. Draw the mechanism for the Michael addition of Diethyl Malonate to the afi-unsaturated ketone B. As usual, put in all formal charges, unshared electrons and arrows drawing carefully. o Me2C=CH-g-CH3 + D'ethy' Ma'onate NaOEt,EtOH l B O “get // CH (.3005ij , —Q&u. ®.Cli(coosf}z_\ M CH 5 J W 1 CAME—r); 2. . Page 7 Organic Chemistry 345 Spring 2005 Exam Za I Name (Pleése Write Clearly) 11. Draw the mechanism for the reaction of benzoyl chloride with methylamine. Include the sigma intermediate. Include all formal charges, unshared electrons and arrows drawn properly. (7“ Wm. -c—-Q,Q'- p’hMt- IQ". _. Mfg ,. _—/—‘7 7,2 -—> [HATS NH M(( v ;L 7,. '9 I 12.A Compound gives a positive Tollens test. What does this signify? {M WEOM 16 M ¢lAVLV0Q . (Answer). I 5 ...
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zimm-exam2a-Spr05 - o #12»- Organic Chemistry 345 Name...

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