harperexam4

Harperexam4 - Chemistry 322a Spring 2002 Exam 4 A Harper 1(15 pts 2(45 pts 3(10 pts 4(10 pts 5(10 pts 6(10 pts Total Name 1 TA 3.64m! l(15 pts

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Unformatted text preview: Chemistry 322a Spring 2002 Exam 4 A. Harper 1. (15 pts) 2. (45 pts) 3. (10 pts) 4. (10 pts) 5. (10 pts) 6. (10 pts) Total Name 1 TA 3.64m!» l. (15 pts) Give the dominant elimination product (only one — excess will be deducted) for each of the following reactions. b) ____» Br 0 1 equiv. EtO’Na+ I 0 K a M [6 2 1/ M f) A? cold conc. H2804 \r u v 9“ 0:? Z/Mcs) 1’ 3 304/ 2. (45 pts) Give the product(s) in each of the following reactions. You must indicate stereochemistry where necessary. If a racemate is generated, you may draw one of the enantiomers, and write “ + enantiomer” instead of drawing both enantiomers. If diastereomers are generated, you must draw them. There will be deductions for showing incorrect stereochemistry, and also if you indicate stereoisomeric products (i.e. racemates and/or diastereomeric mixtures) where there are none. Br Na! 1 f ‘ fiber C I a) Omar _ Edd/,6”? MBA 0; 7/ O PCI5 b) "—“‘" Br excess NaNH2 c) Br —_—_—__> mineral oil, A Br excess NaNHz I d) —— @oac493 mineral oil, A \ OH Cl U @LEC—Cl‘g aqueous H2804 e) --—-—---> ( Q) Mir-vaname > 0 —~—————————---—9 050:“ + h 1 fl“ (3 —————’ & C© MVIQMW> $0” '"C' , ca 1‘. N h) (:ch1 m“; + ;B c" 1 Q }(difimmm)f 3 9) J') k) I) 0% \ HBI’ &/ W 'BuOO‘Bu 0 ©/\ 0 aqueoUS'KMnO4 NaOH, 0°C 2. Zn, HOAc 1. KMnO4, aq. NaOH, A —-—-—-——————————> 2. aq. HCI 1 equiv. CH3COBr C._=_C —-————————> wet Al203, CH2C|2 \ ,2 L "V0 1. 03, CH2Cl2, 48% m“ CED “A m _ MW m H05: @ wfl M jfiy—cm 3. (10 pts) Devise a multistep synthesis of the cyclopropane shown, starting from isopropyl methyl ketone (shown), and using any needed reagents and conditions. You must go through 4- methyl-1—phenyl-2-pentyne (shown) along the way. You do pit need to provide mechanisms. 0 ! ¢ + MQVFI'IW (multistep) (multistep) (CH3)2CH CHzPh Sims 0 9‘ \f’pNuN‘rL céo’H i-NWM Lav/Q . NRA“ u, @/\3, . H1,N'l13(?"z) \ 25 YICQ H...) fiVMOI'W‘tQa CR9}; , A (Syn — Aydmgwhmj 95, 9117,17,)1ACC“) 4.( 10 ovide a mechanism for the following transformation. Be clear about electron mov ment. :OH 5. (10 pts) Compound X (C5H100) shows a strong absorption band near 1710 cm". The broadband proton-decoupled “C NMR spectrum of X is shown below. Propose a structure for X, and assign the signals (labeled a, b, c, d, from right to left in the spectrum) to the carbons in your structure. 120 100 20 aC(PP'“) 6. (10 pts) Compound Y (CsHmO) has a 1H NMR spectrum shown below. Deduce the structure of Y, and assign signals (labeled a, b, c, d, from right to left in the spectrum) to the hydrogens in your structure. 10.0 9.0 8.0 7.0 6.0 5.0 4.0 Chemical shift (8. ppm) 3.0 2.0 ...
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This note was uploaded on 10/12/2009 for the course CHEM 322AL at USC.

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Harperexam4 - Chemistry 322a Spring 2002 Exam 4 A Harper 1(15 pts 2(45 pts 3(10 pts 4(10 pts 5(10 pts 6(10 pts Total Name 1 TA 3.64m! l(15 pts

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