Practice Midterm 2

Practice Midterm 2 - NAME CHEMISTRY 242-001 Spring 2010...

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Unformatted text preview: NAME CHEMISTRY 242-001 Spring 2010 Professor Virgil Percee Second Midterm Examination March 3rd, 2010 11:00-11:50 am in CHEM 102 Total Points: 100 Please put your name on all 7 pages of the examination. Be certain that you have all 6 questitms. Total number of pages including cover page: 7 Please Read All Questions Carefully Before Answering Them Question Points Score 1 24 2 14 "mm-“m 3 20 "mm-m- 4 16 ----------- n 5 10 "Mm-m- 16 ----------- " :r‘i ;-5E NAME (I) (24 points) Provide the missing products and reagents and intermediary compounds 0 . . i for the following reactionsa 3 1&- U.‘ Whig“; [JR 2% i n N H [J EN L P ; NH2 0 i New la a} La. 4:) ‘2 ., n ' AICI3 (Lam‘s FeBr3 h 2PM, and ) if”? “no 2-10 0 _‘ n J 7 EtOH ' __._ ‘ Eu f fiv f‘ffilu-on 2‘7 U 1 I) .z 6) (EACH?) KHnjnomHgonooc ? ' 2—961 0 N,OH o mm‘fi’fi’f .. rm? ? 30+ I d) W ;»; w o 0 ' ' H5fi ». 2.1m L (Q Q R ’Lp’f in mi W Zn(H ) 9 e) O HOWE-:0 ' h {L WIDM gunman-Em M £1. belfifl‘i" 31*!» (fl/m1 NAME (2) (14 points) Give an efficient Wittig synthesis for the following alkene. Show arrow pushing mechanism and provide explanation whenever applicable. mil .25” " “'\\ _ [ P9313} f3 :3 r. n «I'm-Ll /‘\‘.\[;5‘r #4,, /"‘~ 991,53 f—a W Maw/fl] 4?.) {It ‘/ lam [ml 5. 0 lir-g ._.-»,«y L ['10 (y; £642 {flint/ml Rx.“ .SlEfi'L Ifluflélfif‘fvv'ic.c he Corry/l well»? {airflow}; W/o $393.0 3 NAME (3) (20 points) Show all products that could form in principle when the following compounds are heated- Indicate the majorlminor products. Provide explanation whenever applicable. Show the arrow pushing mechanisms and name the reacticm. a) ._m_.® “mew NH 2. A920, heat ' VF OH x FWWVQ prod/14d: (la—Pb CilgI—(fiflflf-ji ygjfi #a—a; \ NLLH3>1 wind" N CH r- C, (& 3)2 l} / H: 0? WA, 3w H Pt» ' c. I)” H < fl / ’ \/ 3 mi 1;“ g _ 0 a N t m fig.“ l”.- 9 lh ll; qu .‘kt’ ‘5 n-{E-rffihfifii (‘ “*1. N fly at xVI’tLhM piggidngi m5)( r l {. a l CH3 m t) H l g! D '! H‘flfl _ 7 /’_—:-< J via. “20“ {11 j { mm D \>N~03 D H I mm: /'\.\,r " v’ F l *4} w A .i w, " W»: mg amt-r21 1, w {A NAME (4) (16 points) Predict the products for the following transformation. Show the arrow pushing mechanism of the reaction from A to B. O N"'2NH2 KOH, heat 3 H+ . [NH _ “g H. Qpfi M iv ‘34)}; V/ A pt, --- is {95:- -‘”"WRJ qu ice t—w—Eal 6’" -[\“ v iAfi N/NH Nflwn Hrs“ HérJH. 1 "on h ’ ’ Fin/\A/ W W H pf/VAMflf—i i T! L?“ rte 41’" ’er 90h ’1 {r fe- J‘N r/LFh LC; 19111W5 on 3+0fk) nph # more; mm » WW MPW 0W " Km cu; Magma) 03, [moi-m 1-3,?is H® Kort @W -. ray: x Mo {yoth CAM/(WV ’3‘“ wf‘ha Kw mme 49 aarm A 3‘ 'm NAME (5) (10 points) Rank the basicity of the following bases from the least basic to the most basic. Provide a brief explanation. a V 7.. S s. ‘5 3 F \. NH l? N [‘33 C” J 8? D H3C—NH2 l / 2T: 0/ (2:; 6) ca GD @ Wotl bogging, Law's" Lianne #QNs W Paid” WE»? J? EsMFoQ/v ’1— Fu'rr —& pix “mini i, gwmfi» gram. MW . 3 J MFPJF * ExpLWh/én '- rep Em lame mm sob/(M’s We my 3? mmmbshwwi Cmmvfic 9°lW+C€1 45! M law was #3 “Lo Wrmewwez lam/h}, mam 3°mriore -— Eirfle 1026., WWHL/M “At/w e} 4161' re”? Wi— O’vs ‘0qu _;. ken/«Jr J is WLMIWWLtW- w { viii. pr 5W0 W hthLO. «rig: NAME (6) (l6 points) Predict the product and Show the arrow pushing mechanism of the following reaction. 6) Ear/u. \lbfim MFW if)?“ “U 39+: ‘9 Hg? <_-\ ‘ Fa. ax “v” w T mi (243 .. H940 ...
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This note was uploaded on 03/07/2012 for the course BIOL 212 taught by Professor Kina during the Fall '12 term at UPenn.

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Practice Midterm 2 - NAME CHEMISTRY 242-001 Spring 2010...

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