Sp11-Final_KEY - C H3 10/318M F inal Patman S p.2011 EID: (...

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CH 310/318M - Final Patman - Sp.2011 Name (printj: lf you think you may want a regrade, pleas€ use blue or black PEN! Please write the first three letters of your last name in the boxes Please do not ask the proctors or TA's to intetpret questions for you. The goal of the exqm is to test your understdnding of the important concepts we hdve discussed thus Idr. Sufficient information is provided to make it clear what is being osked in eoch question. It is up to you to interprct dnd redd each question carelully ! Pleose moke sure you ore completely aware of what we are dsking you - only then will you be able to fully dnswer the question. Pace
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CH 310/318M - Final Patman - Sp.2011 Mechanism - epoxidation. Push the arrows to depict the mechan peroxyacid, and answerthe related questions. Be sure to include ch!rges as necessary. l6 pts) 1) EID: m for epoxidation of sty ne with a al styrene oxide (racemlc) RC03H stytene an lmDo anl monomer lor materlals/plastlcs (1.e. Styrof oam) .t-t . A common peroxy;cid used is nCPBA. Please draw the structure of mCPBA in the box (1). . Why does this reaction produce a racemic product mixture? {should take ,1o more thon a lew \Nordsl \2) /-\ I Nwv Osd,i?.t-t- Colrr CI^rr^ t t t ,i f\ ktvi lDp c-l bottwr*a-c-r- nU. . \ ^, . t- {,r'{+. .1'
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CH 310/318M - Final Patman - Sp.2011 EID: 2)Thinkl communesin D, of the communesin family, was isolated from penicillin mold. This natural product has garnered interest from the synthetic organic community since it shows potent antiproliferative activity against leukemia cell linesj several attempts and syntheses of the communesins have since been reported. Communesin D was found to have the molecular formula crHraNaor. Exhaustive (complete) hydrogenation of commun D wpuld yield a4mpound with the molecular formula carHsaNao3. Please fill in the blanks irts) <x.b # DOU'S: # rings: net dipole LtKe your Erl!.-'Pi" lPr flL n.c/s{cn. H3C-C=N ','-(t*-t o ", C5'l-e.no[ Urr (evigx! BeESiMrr moment in homeworkl # [-bonds: For the owjr€ compounds, use the dipo e moment symbol to show the direction of the all the polar molecules. Draw a square afound all the non-polar molecules. (HINT: you may need to consider the most
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4) Conformational Analvsis. Consider 2-bromobltane (below)j the energies corresponding to the various ions are also given. (8 pts total) Hsc\.,,Acrr kcal/mol eclipsed eclipsed H-H 1.0 kcal/mol €clips€d cH3'cH3& 8r- cH3:3.0 kcal/mol CH 310/318M - Final Patman - Sp.2011 EID: a.) Draw all staggered Newman conformations from the perspective of "the eye". Newman projection *1 should be of confofmation given, and rotate the back carbon c ockwise only. Square the hi8hest
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Sp11-Final_KEY - C H3 10/318M F inal Patman S p.2011 EID: (...

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