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2008_05_30_16_13_29

2008_05_30_16_13_29 - 0 ton no CHEMISTRY 1408 NAME(ptease...

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Unformatted text preview: 0 ton no? CHEMISTRY 1408 NAME (ptease print) . EXAM 2 (GP 13, 14, 15,- vas 5*“ ED) FIRST .4 .. March 3, 2008 — SIGNA TURF. _ _ ID NUMBER_ LAST NAME OF PERSON SEATED TO YOUR RIGHT LAST NAME OF PERSON SEATED TO YOUR LEFT.‘_ DO NOT OPEN THE EXAM our". you ARE TOLD TO no so. — Ptease sign your name on the top of pages 1 through 6. — Please check that you have 7 pages (including this one; page 7 is blank for your scratch work). - Answer only in the space provided. Do not write answers on the back of a page. Question Points Score 1 16 C) 2 40 Z S 3 24 ( 4 20 ‘4 Total 100 {3 H He LiBe B-C-NOFNe Na Mg Al Si P S Cl Ar KCaScTiVCrMnFeCoNiCuZnGaGeAsSeBrKr RbSrY ZrNbMoTcRuRthAngInSnSbTeI Xe CsBaLaHfTaW ReOsIrPtAquTleBiPoAtRn 1a. _ lb. NAME (8pm) Propose a detailed mechanism (curved arrow notation to show the movement of electrons) for the acid catalyzed reaction shown below: r/Jxvx o“ catalytic W0“ ”hi:- N 0“ N ZSOH (8 prs) Propose a synthesis of the following molecule by a Diels-Alder reaction. You may use any starting materials or reagents. H t' EU“? Why does the synthesis of this tricyclic compound occur below room temperature whereas most Diels©Alder reactions require heating? . @c 3 WLQ WUOTWWJ‘O/ ’2 2. NAME:_ (40 pts) Predict the major product(s) for each of the following reactions. Write "N0 REACTION" where appropriate. All chiral starting materials are optically pure. Show stereochemistry where appropriate and write “racemic” under your product structure if it is formed as a racemjc mixture. /\.- -. z:——-/\ a) ' ' ’1. . f — 4"“??? m {‘1 '- mi H2804 Etht r 4. _— *7|-- H20 a /“/Y\ Hgso4 O b) Kl WBr . acetone \/\‘\, W\ C) HBr M heat ”11% sfrmkc NBSJ‘W COL; Li : THF A/fig/\ ,6 O d‘vx J) 2) 020 fuming H2804 Brz H2O NAME: _[\_J (24 pts) In the box provided, give the reagent(s) need for each of the following transformations. More than one set of reagents may be necessary for a given transformation. 8) b) C) / MO .1 MR3 \ : M H-79 d) _ - ' 1) “mg 11+]!!th . Q/ '2) W . W e) i.) HEY?- 0 Z) HOOK, otL’ /U\/\/'3)Wl’i K 4) ?CC 916; 5 W ,_._— —_ NAME:_ 4. (20 pts) For each of the following one-step transformations Show the movement of electrons by using the standard curved arrow notation. Show all formal charges for each structure to the left and to the right of the reaction arrow. H “OH H ®O_H Cng ...
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