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    Organic Chemistry

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    Organic Chemistry

    Copyright:

    © All Rights Reserved
    Download as PDF or read online from Scribd
    Flag for inappropriate content
    7 views10 pages

    2014 Exam 1 Answers

    Uploaded by

    Edward Parker
    Organic Chemistry

    Copyright:

    © All Rights Reserved
    Download as PDF or read online from Scribd
    Flag for inappropriate content
    of 10
    mc for forking a Chemistry 0360 Exam 1 - September 29, 2014 Only answers written on this exam will be graded. There is an additional booklet containing spectra tables and information regarding question #2. Graded exams will be scanned and retumed via email. 1. (24 points) 2. (26 points) 3. (12 points), 4. (12 points) 5. (8 points). 6. (9 points) 7. (9 points) Total (100 points). Page 1 of 10 NAME: 1) [24 pts] Each reaction sequence presents a starting material, reagents for two sequential synthetic steps and a proposed final product structure, P(A) - P(F). For each reaction sequence, (i) provide the structure of the first reaction product (A - F) in the correspondingly labeled box; (ii) if the proposed structure of the final product is correct, WRITE CORRECT in the P(A) - P(F) box. if the proposed structure of the final product is incorrect, DRAW the correct structure of the final product in the P(A) - P(F) box. i HO, Ph [PhCu]Li 4) EtLi Stecaeas ciara 2)H20 PIA) Br 9 oO ys eo 2 EMRE |'p| 23 HO Et 2)H,0 HO H2804 Pe) 9 fe) od 2Li HO-$-Ph - = The aed ce ao Hz0 PC) will peofo neha the qaiosic Cin ree before ony o thee chemssbey Br Page 2 of 10 NAME: 41) continued MeO CN ° Nco ("| 4) NaH O L@® Coy (emech) O ae 2)Me-Br P(D) 1 Ta theobsence of o HF isoucce NMeg = Os) a! eeeeeuebege (fps | pence Boe ee) [| pHS P(E) NMe, ° © Br._B >| pnsp—Z, TBARS 2)PBrs PEF) 9 —- tBu Page 3 of 10 NAME: 2) [26 pts] The accompanying packet contains a roadmap of reactions emanating from the starting material 2-methylpropene. Spectroscopic information for structures G and J is provided in the product. (nb - It is possible to determine their structures without using the spectral information.) a) In the boxes below, provide structures for G ~ L, and provide reagents for steps 1 — 5. 1) BH; or RiBH 2) W202, HO? (DD Nal ec NoNAe oc Bole Page 4 of 10 NAME: 2. continued. b) Redraw the structure of G below, and assign thé 'H NMR spectrum for this molecule by writing the chemical shift of each type of hydrogen next to I ucture. x 540.0 — on a ip each . [340.2 a 1 pf doses Ae oll U corre’ c) Redraw the structure of J below, and assign the 'H NMR spectrum for this molecule by writing the chemical shift of each type of hydrogen next to it on your structure. 42rO.d O4 46.2 ees © { ie | THO. | pr eee gent £00 J Lyall my +4 pt bones tor ZGtor 3 correc Page 5 of 10 0140 ge6eg gh elayg dg sant) i qf 2 ae " a4 om + ff = H* bl = AvHI # Vv oe 4d 1 sehaye qd & sane sd 2 2749 ef = = hc A8 le t so et n hey me, 1 4 eo” i V7 - PR Ge * !seBreyo jeuuo} Je MOYS (0 :Burpuog Jo seBueyo moys 0} smoue panuno asn Ajjs105 (q ‘Jonpoud 0} jue}oeeL Bunsenuoo jo sseooid 9y} UI pawuo) seyeIpaLw9yu! [je ue sda}s jeo1WeYo fenpiAlpu! ey MOUS (e SMW WISIUEYOSU INCA “SUOHIeAI OM SuIMO}IO} BU} JO} LISIUEYOSW Palre}ep e apiAosd [S}d ZI] (E aWwN NAME: 4) [12 pts] Provide detailed mechanisms for the following two reactions. Your mechanism must: ‘a) Show the individual chemical steps and all intermediates formed in the process of converting reactant to product; b) Correctly use curved arrows to show changes of bonding; c) Show all formal charges; 4 ockee aps per ee acrus aps Me QI YD os! i csi Ee. charges tpt Ses O-Me ° @ Mosolctel core foe +O, po why! WS a @CHs forms 8 , a CY als +PhS a order zpts Cian ee “ie De chaqe a yh pot oy ae fie skp ‘ ve $58, 1S + 5? he of Ph he eo Ths bechsibe gag ol Jo the 5?hy fecery j yoenp Sw2is possible Sei at the 3° C-LE becuse No is Le Ph pageTotio — permaneatly, poscwoed c co the poupes | foce dion fr NAME: 5) [8 pts] Propose a synthesis of the indicated alkene. Any starting compounds that contribute carbon atoms to the product alkene must contain three or fewer carbon atoms. Any starting materials with ——> ae eesy 3 or fewer carbons at — Mansy seas fo do this Ralesaythoy © aS ay ay ¥ ° ay “Be + Ry patie Aye i a on me AH ioral ol ae oO Es rs Product ve a T+ Phy —> a, Bp, MEE se ft, Deity Bote Retrorgathess joe eee S ae ea =] T $ Hebe 4 pb § poke Noe H~Be Gi “ye vc) & eo Ae ara ie . ae Peed : oer oe Pe ee eo: tg ans SO Poe is Raoaathod OS ae 32 4" Mig” +o® Me MBe 6 Cl See oie oo pe ie Pe Abore fur GMO AT Uo = g rer 1s $B other cols con wo Page 8 of 10 NAME: 6) [9 pts] Propose a synthesis of the aldehyde on the right starting with ally! alcohol (molecule on the left) as the only source of carbon atoms in the product. You may use allyl alcohol as a starting material more than once if necessary. H oo aw —-> a fo) (eres ae 3 Tico Be preces con be combrard to meke he rndrected Ee bord Need one 42 be a cecben Nut and one fo be & Corben electrophte Cannot vse Pe] LA no Bey fH ee on Fo. Rego cath 3c nucleephle PeAraniidle Pee to cee eS iegae Le ia Ga . epee Be ete MS ap [AR+~=] Li a Simebee tae Bev. 2 1 Bone gp iy Reber, 4 we 1 > mo, Mee mscr / er Soci, , He) teed cE At le ett 2A oH t-Pe Bet ew be Deeb Sueca ¢ (erSee, Bs (Hw) D Wee BeNeN Be "4 essa Be curl ZrO To ee + fhe Whe rene | [rs- alcohol } Wee ts Be ae tape” Se get beth mm be Page 9 of 10 0130 01 e6e4 (er) aap > a wnpeny) ae) nou a Bese ce me oh oe a err i= aaa N Lp OSH Ce nw W Vv 5 x fig FS

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