examkey2-2001

examkey2-2001 - Last Name K E j - First Name Student ID#...

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Unformatted text preview: Last Name K E j - First Name Student ID# Chemiggy fl — Hour Exam #2 Wednesday, March 28, 2001 General Instructions: (i) Do not open exam until 9:55 (when bell rings). (ii) Use blank paper on the back of each page to work out answers. Final answers must be mitten leginy in the space provided. (iii) Print your name on each page. *“No credit can be given for illegible andlor ambiguous answersf" §ra_de page 3 [12 page 4 [22 page 6 [18 page '7 [20 page 8 - [26 correct room? , _____12 TOTAL [100 (Substantiated evidence for cheating or other misconduct is grounds for automatic course failure ' and subject to further prosecution.) Name (scratch paper) Name 1) a) (6 pts) Provide the structure for the molecule, (Z, 4S)-3,4-dimethyl-2-hexene. 4- en'sld'cm SQmMSHj . b) (6 pts) Provide the correct IUPAC name for the following molecule: HO CI '- 3 "‘ (Lt-loco -- -—_-‘_.——u—I— 22k: \ 9E 29% \ ob Name 2) Provide the missing products, starting materials or reagents. Show stereochemistry Where appropriate. It's not necessary to show solvents. (Dang:- Harkb‘hlflkkw ' “Ax‘ficw- 0" Hgv 2-753 {Fl M5!- ZLI. of ZNm. ‘ M awn: a. rug Q’m Mo‘un Name 3) (18 pts) The energy diagram below displays the energy profile for an 8N2 reaction for the formation of methanol from methyl bromide and sodium hydroxide CHsBr +NaOH —-+ CHsOH +NaBr Energy —---- CHgBr + NaOH CH30H + NaBr Reaction Progress —-r Now consider the reaction in which tert—butyl chloride is heated in a polar solvent with sodium bromide. Two different products are obtained, tert—butyl bromide and isobutene (see reaction below). At most temperatures, the 5N1 C] + NaBr CH3 ‘ ‘ Br + /ECH3 GHfiH3 CHfiH3 CH3 The relative energies of the starting material and products are shown on the product is favored over the E1 product. CH3 CH3 energy diagram on the following page. Complete the energy diagram. Include the following items: (i) Identify the appropriate energy for any intermediate(s) in this reaction. (ii) Draw the structurets) for any intermediate(s) in the reaction, clearly indicating thethree-dimensional geometry. (iii) Connect the starting materials, intermediates, and products with suitable energy profiles for the overall reaction. Because two products are formed, your diagram should consist of two superimposed energy profiles. Energy Name Use the back of the previous page to work out answer bg‘ore draufingfiml answer on the diagram below. Illegible or ambiguous answers cannot receioefidl credit. ' RCMdh‘e‘N c‘r gash. m’ru-md . I 0" EDA:an \nwm rah-.— awninal \S'. "‘ M \DoJ'I’utf —5~b€lQH-J‘erm\£ - Too-max \m.a\:n3 1m (amt ewe Maw Mme. \QE 0 \“HM W \4 PE ’ Carma} FAG-5h.” thm D“ ‘(LWNA . \er‘rs Reaction Coordinate Note: From your energy profiles.r it should be evident that formation of tert- butyl bromide is favored over isobutene. Name 20 4) (fivpts) Use retrosynthetic analysis to illustrate how the following pair of molecules could be prepared from 1-butyne. All necessary reagents should be shown. ' Brl—l \)Y + enantiomer HgBr (It is not necessary to show the forward synthetic scheme or an arrow pushing mechanism) EX 2L1 ,EhMHl \11/ “:__""> + QWL :é \p-E'fl—*¢“‘3 I Name 5) a) (13 pts) Provide a forward synthetic scheme for the preparation of racemic 2-cyanopentane from 1-pentene. Provide the necessary reagent(s) and an appropriate solvent for each step. CN MiM (racemic) _ 90.; an“ no? 3AA \‘o Adv-m5 halt: a. Carla-Hai- b) (13 pts) Show a complete arrow pushing mechanism for your synthesis above. Indicate any unstable intermediates by placing a bracket around the structure. Name PERIODIC CHM?! OF TEE ELEMENTS INEm EA ms. ma NB VB VIB VIIB wu IB IlB “IA WA YA 91A Vim mass _ . flfi gaggm; _ . fl @% r I Tc I I - s c Sn Te 35.4! 83.82 92.506: 95.91 [99] I! 113.69 12?.Efi12638‘f CsB TaWR Hg b P At 132.995 136 138.8} 1&3“ 133.35 338.2 200 28? 19 E238 {2!fl I E2231 {2”} E Efifififi Winan *mem 3m mumnwhww Z 0 M 8 E Hg Ptm:r 0 192.2 195.” 196.93 H S :1: 'I ' 'r s [285] [253} {271) fi$ 02.905 E 0' E: O E .3415 91,22 195.1 T! 201.3? i 208.950 HE C" m u Ea : w $30 mum. : -! i a .i' r :7 :-' :T: i' i' : 'fir' ' mmmhfimmmfiggmmfigmmm Wm M '1 | i a .I’ 5' 1';- EE.‘ .- ! : ! .I r a .r | I “31 E®EM®Q fi§%mMEE ...
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examkey2-2001 - Last Name K E j - First Name Student ID#...

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