MIdterm 4 - Summer 08

MIdterm 4 - Summer 08 - \ Pom Iva Chemistry 322 bL Name...

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Unformatted text preview: \ Pom Iva Chemistry 322 bL Name Basic Organic Chemistry August 4, 2008 TA EXAMINATION 4 Answer the following questions in the space provided. ease organize you make your answer as legible as possible. If we cannot rea ur answer, it can attempt to e given credit. Please remember that C-C-C-C without hydrogens and “stick” structural representations will be given N0 credit (except for rings only). You may use the backs of pages for scratch paper. 1. (15) 11. (1 s) 111. (36) IV. (21) v. (13) TOTAL (108) Read each question carefully in its entirety. Check immediately for 9 (including this cover) different, non-blank pages in this document. Chemistry 322bL Examination 4 page 2 August 4, 2008 I. (15 pts) Provide names for the following structures, or structures for the following names, as appropriate. Either IUPAC or common names are acceptable. (a) 0 <3) WRch N— l 6: WM MI (b) CH3CH2-IFIH 9 C|iH3 CH3CH2-CH2-CH2-CH-CH2fiJH-C-NH?CH3 OH CH3 , mm“ (c) N-propyl-m-formylacetanilide O cucnpufmiwg <é> } :WKM II. (18 pts) For each question below, put a mark in the space provided or @ the best answer, as appropriate. (a) Give the pK'a of the following acids (+/- 1 unit). 4' OH (+)NH3 O OH (WEB i) © _l_"_l_ _J|__ _l_0_ O H (+)NH3 ' ‘ (+) 69 0 CH3002H (E H3O” \ 2 S’ S’ g Chemistry 322bL Examination 4 page 3 August 4, 2008 (b) Which is the most acidic and which is the least acidic molecule below? (Fill _IM_?0_ blanks.) OCH3 F N02 OH OH OH OH OH mcflF gmz cmog ozNOMmN/QOCH: __ M < (c) The most acidic molecule below is \ O O O \ \ \ \lC—CH3 \p—OCH3 \p—CH3 C\Hz C\Hz C\H2 /C-OC H3 CHz-C H3 CH2-CN 0/ \ or d r" (d) The molecule that will react most rapidly with KCN in DMS is N02 OCH3 Br CC” (EL < ,1 > I NC F OCH3 H30 /CH3 H3C\ /CH3 HaC\ /CH3 (+)NH H3C CH3 H3C CH3 (+)NH (+)NH : (5N ’ (gm < > i i N Chemistry 322bL Examination 4 page 4 August 4, 2008 [I]. (36 pts) Give the main organic product(s) for the following reactions, or provide reagents and conditions to carry out the indicated transformations, as requested. More than one step may be required for a given compound. Be sure to note product stereochemistry and/or regiochemistry if the / Ll question explicitly shows it. You do M need to balance the equation, show byproducts, or show any mechanism. (Note that “No Reaction” is always a possible answer.) (a) O H 0Na (1) coz, 5 atm H20, 120 °c @/ C 01H ——-———> \ (2) H30“) (C) 0 1) KCN, HOAc @ 2) LiAlH4, Et20 (:EKCH NH )- 7 3) H20 " d 1) excess CH3I ( ) CH3 A920, H20 <e> —" Chemistry 322bL Examination 4 page 5 August 4, 2008 (6) N02 1) Fe powder, HCI H 3) NaNOz, H2804. H20. 5°C CH30 QC 3 4) H3P02 (0 Br 9H 02N N02 1) NaOH. H20 CAN /\\/N (33 2) H30+ N02 NOl (g) [ICHZ‘QW .____.NaB“ac“ m 1% M7!- CH2NH2 CH30H N Nee-4 ‘ O :4 ’ ‘ ' \\ —9 f o X! ‘0 H P (h) NH2 1) NaNOZ, H20 / 0 H2804, 0°C )\\/1 CH O CH O ‘ 0C”; 3 OCH3 2) HBF4 3 3) heat _ O excess ‘ 1L L (l) NaOCH3 CH3CH—C-OCH3 (EH3 CGHGN M 0 A 9 J <3> MC LtH-k-é’ / dilute H30+ Rafi +10“ . ‘ workup “~—————- Chemistry 322bL Examination 4 page 6 August 4, 2008 (j) 0 (1) Li N(iPr)2 C3 THF, —78 °c 1 ‘Kru‘il ‘ $5 (1 j (2) ©0H2—0| v (3) H20 workup (k) 0 Br ER” 1) NaN3 grfli’ NHI W”; U 2) heat, H20 \ \ fir / C ' \ ' d“. f IV. (21 pts) Provide reasonable syntheses (i.e., minimum number of steps, good yields, good stereoselectivity, good regioehemistry, etc..) for the molecules shown below starting with the indicated starting materials and using any other needed reagents. Be as specific as you can regarding reagents and conditions. Show the product formed from each important step of your syntheses. Be sure to indicate if a step results in formation of an ortho—para isomer mixture, but assume that such mixtures are readily separated. (a) ethyl acetoacetate O\\ /CH3 + organic reactants of ------ - - > (f 5 or fewer carbons CH2:CH—C Hz-CH—C H20H2-002H I) G'qukliv NaOEfi z) QM): cu @410 N W) C O "‘ C Q; I ». ‘ CH =UJ~LH ~CH-C CH 6 J ) go 56 5 Wayne ‘ mh=CH<H,—eeq_cug am an mow u o; 5 Cu=mrrmEé \ bkmmbHfi ' A emuhanEe + mn:cu0£~Q—%~CH3 €>H30 l 0 E696. Chemistry 322bL August 4, 2008 Examination 4 ~ look 6 m - (b) C02Et O CHZCO H /”\. NW 002Et """""" "’ 6/ 2 \ J CQLH [ID . CeHc» N b “040$ A 2) H30 ‘ ?) 01" 1%;an O 3 f w _ J “00136 /.;\ 4041C033? WELL _.__y L] cgEé ‘ 2> CH; L01 D": {2r ow (c) CH3 CH3 2 i H HAND; <5 ___________ 67:60?” fir Niacin? . . - g OH Br H20 0‘) z “:0” 1043 C N00 L; ¢\ Hm; Hp) ~ LW H,$OL| '73: (Hi: (Illi’f? ‘ \¢\. / V/NBL / \ % IQ/U\MO;+ g/H < l (5r (\f" N14 Ac 9 L (290nm f ‘ , ~ CH3 CH DH': (WM . , «my \ W ? i |N)J 2) mow NH («Hs'h‘O \ NOA 2 NH} Chemistry 322M. Examination 4 page 8 August 4, 2008 V. (18 pts) (a) (Toncisely explain the differences in the pKa’s of the protonated amines below. CH30H2\'q/I:CH20H3 E «V (CB w w p1<a = 5.32 7.23 10.82 {C} MM » Va. a Owing, (owe . (0) W63 (lg; (wake/3t W16) Wmaefifl m (mm M 1110mm dflQataQ/Uaewl W 363 Wébfidmezl Carlocva arBH—aQ c% Sf“ a a aw m a ‘ N Z I , Cbgmlofa Sqmo°% “Hm ‘g fiAzé‘W amounts of ring alkylated products are formed. Briefly explain why. < L? ONa 1) PhCHz—CI OCHZPh OH OH . H20 CHzF‘h 2) H30+ + + CH2Ph small amounts Chemistry 322bL Examination 4 page 9 August 4, 2008 (c) Provide a detailed mechanism for the following transformation. There are three (3) generally accepted intermediates and one product in this reaction, so only four structures will be graded. Also, l show in each box the arrows appropriate to rationalize the next step. The quality of the electron pushing will contribute to the grade. ,4 excess 91) NaOCH3 H30+ ii i? CH3CH,C—OCH3 Product ———> CH3CHZCCHC—OCH3 [J C6H6ll workup 6H3 QlQCSAL/lu ...
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This note was uploaded on 01/22/2012 for the course CHEM 322B taught by Professor Jung during the Spring '08 term at USC.

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MIdterm 4 - Summer 08 - \ Pom Iva Chemistry 322 bL Name...

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