CH151 Exam2F06KEY

CH151 Exam2F06KEY - El E3 DECIDE Organic Chemistry EXAM II...

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Unformatted text preview: El E3 DECIDE] Organic Chemistry EXAM II CHEM ISIL October 30, 2006 NAME (Last, First, MI.) Write the first letter of your last name in the box. Instructions Please fill in your name in the space above and on the next page. Print the initial of your last name in the box above. Sign your name under the Community Standard Acknowledgement. You may use pencil. Answer questions in the spaces provided. If you need extra space please write on the back of the page and clearly indicate that you have done so. If you do not know the structure of a molecule given by its name you can “buy” it from the TA for 1 point (each). GOOD LUCK!!! ' 1) (24 points) For each pair of molecules shown below, indicate the relationship: enantiomers, diastereomers, constitutional isomers, or the same molecule. HO tl HO B in shay \EB-(CH2CH3 WM: 3) H“CH33r CH3 magi-j, Ch 25%: Same. MoiCCuiC... cndn imam h /c|s:,011 H—|—-CH3 H—l—oH3 (.5 H _\I‘ “in:i//(.‘\®Culrtll'B d) CHQCH3 CHon ahcb than 0mg 5 2) (12 points) a) Rank the following molecules in order of decreasing boiling point (1 = highest boiling point): x0“ M X/OH + '1 W .3 L __ - l = b) Circle the solvent that would best stabilize both of the ions formed from P dissociation of NaI. ’ i“ :0: W 0 ‘L HacJLCI-Ia V V (a PA. ‘PA \‘W "i eh 0 ”PB (0 Pt M05“ CWt‘al/Achiral/mt'so : L/Pi'z’ fad/k :10: Each Cisjmme “if. C. 1 apt X"; C‘hL‘T‘3 :Q’ 3) (24 points) Label each of the following drug molecules as CHIRAL, ACHIRAL, OR ACHIRAUMESO? Label each asymmetric carbon as R or S. a) 0 2 H OH I 4.! .. H1" "IH 4_ H ~ 0 / 5 5 NH2 Ho .- MIL/(d W 0 Cloud \ ' °” N O H SH H 2.3-dimercaptosuocinic acid tryptophan “used to treat lead poisoning R (0046: claim I I H H O O/H" Promc f) OH 0 c‘ ‘ . . J1. Adm ml H 0 F36 J Ch 1m! Ht H J" f3 \ . 0 9H CH3 Aspirin H Prozac A), .3 4) (40 points) 0 For all of the following reactions predict the major organic product(s). Show stereochemistry CLEARLY where appropriate. Mechanisms are not required. 0 Clearly indicate whether the product mixture enmsh’omtrs *’ C Uh («Ducal m‘w 5) (15 points) Propose a mechanism for the following transfonnation. Show all intermediates and be sure to include formal charges where appropriate. You have not learned this exact mechanism, however, it is closely related to a number of mechanisms you have seen. Rely on your knowledge-of the basics. You can do this! | (— chrfludeo¢~t U) f 6"”? ‘9sz “framed, 5': brMWIUM w"- .- dr wwrmm Iw._Ca-bm§ (via/{rum _ ‘ ' \ , / . \ | . (Li/[)— “3/ A a 3»mm\9¢e4 rugslwgdb; Ll 6) (15 points) The following products were isolated as Recall; racemic mixtures from the reaction of 1- lab: _§_© phenylcyclohexene with chlorine. Cl Ph CI Clz ‘ ' 'Ph ' lPh I IH + . . .0| 0| H + enantiomer + enanti mar An @3414 a) Circle the molecule you would expect to be the major product b) Propose a mechanism that can explain formation of the other, unexpected product. ‘Wat use—mt“) my 4sz . i, inwmeDM-‘r ; (3+ 0V C, C 5+.“ 3/9 L‘jb’fiD-i isms!) Sigtia/ +0 Hf) H305 @441in {oi—ir- CIQ A ”C j H \\ Cl \‘ , <2 \\ \\ mt CJ-C‘ ‘\/-\\ ___9 b V 7 CI WU O\‘(~€n€., fl-ppm‘xdk QM Gorbachgla EX cd‘ MN 0-? gilt" \ “63th 2% RCA—‘1“ anoo‘k [email protected]"0qd« Q‘Mh. J . *9? i Em, C) Using a combination of structures and words briefly explain why this specific addition was non-stereoselective. fiwzene No (on “VGA/{2,3 Care/1474A) rm fame ”V (90* 43-99 _, . Ci |\AC_| u“ Q-D “a . I 7) (20 points) Outline a “synthesis” of each of the following molecules starting with an alkene containing 7 carbons or less. Include the structure of the alkene starting material and any reagents necessary. Full credit for pathways leading to the fewest number of by-products. ' Br W ,r’ ”O” W CV ...
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