2005 E2 Key

2005 E2 Key - @QMMNHL 5?an El Ke‘i Exam Two Chem 220A—...

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Unformatted text preview: @QMMNHL 5?an El Ke‘i Exam Two Chem 220A— Organic Chemistry October 26, 2004 NAME: Printed "I pledge my honor thatI have neither given nor received aid on this examination." Signature Part 1. Theory l. Draw this compound. 3 pts 4(E), 6(Z)— 4,6-nonadiene—l—yne H l H — I; lie; ~~ gar; .: .1." _ g_ 2: g” «c. Hl‘L i l l H i“! la 2. Rank the stability of all four alkenes from least (1) to most (4) stable. 3 pts CHZCHa CHZCH3 3 Z 3. Rank the stability of all four carbocations from least (1) to most (4) stable. 3 pts @ ' ‘a’t l'L @ (9 V Val "7 l .3 2 4. Classify each reaction as addition, elimination, rearrangement or substitution. 2x 3 pts Br Br-Br >9 I hv Br ” A\ -i\ \CLYN Br-Br \ CA” L $ ' \ ’ CC!4 Br 5. Provide the specific name of each of these elimination reactions. 2 x 3 pt (eg. osmolylation, cyclopropanation, bromination...) water, heat KOH OH acid \ Q‘ Q \‘ CK \'" (fiifi C \\ ><Br/ Ethanol 6. Complete each statement below. 2 x 3 pts . "X (Stew-vvcx OVA Cb T) \‘(1 <3 Liaik kcl-N’W l o . __i OH / L/VKL.‘\ \An;x (LRC‘vKJL Q H104 —-——-> H20, THF OH \0 r \4 i "N: . The tartin materr l / roduct must be g syn! anti éfc‘re’one Circle one kl“; LVCXL'V were: C‘LKC":‘\3 beeaase~ OACXL - "1L. \«CC‘KL c {to lawx J ‘1‘" ‘ sic \JV'\ up»; CIK Br Br-Br ———-——> CCld Br ’7" \ The starting material /l Erodugj must be syn/(anti because __ Circle one circle e ix 0% \D» \C‘ VVW C-"VX \ UV'VVW kcdx (AA (“Xenia-’3 JV“ ‘k'Jl-Qx- LCM L4: “\1- V1 l H "‘ _ / 1 [LL CL 53,-; +1; t iv. \1gcwl (:1 .2: ct LJxCW-‘VW i m: I! Ch Lynocplkccki Q. {/SJ’E- l: v\ L. ¢,(,,cv1,:\,cL’xo\ 0:61 C2, o 7) NU" ,..\ 7. Calculate the degrees of unsaturation. 3 pts 8. Determine the stereochemistry of the alkenes shown. 2 x 3 pts L, f/ C) A “ H I ’ p \ COOH Kv/ CHO C - H H (.2 9. What is the substitution pattern on the alkene? (Mono, di, tri, tetra) 3 pts Br 10. What is the degree of branching on the alkene carbons? They may be different or the same. 3 pts 11. Describe Zaitsev’s Rule. 4 pts (Y ( rye“ L \ VV\C.V3 ,t Ex» CE‘A'LLK‘K- Ck}\-llf~\ CN- \i) (“4377:3- \ \j‘ mime-m lugs—L x!) 6:» choice -\ ‘. ,’\J Part II. Reactions Predict the product, provide the starting material or provide the needed reagents for the following reactions. (3 pts each) / Clz H20 / H-Cl ————————B> ether l KMnO4 excess -—-———-—-—-> H309 HOH 1.0504 —————-——I-> 2. NaHso3 H20 CH212 -——-———> Zn (Cu), ether /\V Lil ii k \I} ‘ .Kgy” / / (l _) Ht \ {, M ,'/‘}\ . ‘ //’F C l // r ‘ (I, (i ) Q.. N ,3 \l N BHyTHF H202, HO-, H20 ’ l.Hg(OAc)2, HOH. THF —-——————> 2. NaBH4 2 equiv C12 1 equiv. HCl rt:- (7, ‘: " ‘ r H2 C. : (.2 Zn, acid / q R / CHC13, KOH ‘ ,k -' Q/Q/ u E ’ Part III. Mechanisms _L. . X KI, H31304 : HI / a + ‘\'—i\(mv'—E f 03 (a) 10 pts Cl Cl (b) 10 pts ///—\ 0;. E I a V, , >9 H2804, HOH \ —-——-———-—-——-> heat [)zt> ru( T“ i \f t f \ L H2 \ 7 ”/’ , ‘rzll‘ //,___\\ H ‘/ Hac i1 ~ Part IV. Synthesis Problems Provide a synthesis for the following molecules beginning with the starting material provided. After each reagent set show the product. (a) 10 pts (This cannot be done in one—stepll) \{ \‘Z . H2x PClk-Ci \) /J Li \chLzKN , Kc, H, Ll” ...
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This note was uploaded on 04/07/2008 for the course PSY 101 taught by Professor Gauthier during the Spring '08 term at Vanderbilt.

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2005 E2 Key - @QMMNHL 5?an El Ke‘i Exam Two Chem 220A—...

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