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PracticeExam-5-C (Key)

PracticeExam-5-C (Key) - Fifth Practice Exam C Chemistry...

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Unformatted text preview: Fifth Practice Exam C Chemistry 8-20 ii Vi . ,J .71, it? Last Name: £3“ First Name: Cm +0 Section TF: , Important Notes: “Eng—.12....—u...l_.‘.._‘.....’....._‘...._w._.... 1. This exam consists of 8 problems on 8 pages, plus this cover sheet, and one page for scratch work at the end of the exam. 2. All answers must be written in the spaces provided. Do not write anything in red ink. Answers written on the back of a page wiil not be graded. Anything written on the scratch page wiil not be graded. _~ “mmgiéflfissgflu.";..tm-_.........c..t_ Chemistry 820 1 Name: 1. Each of the following transformations can be carried out in one to three steps. Fill in the reagents required for‘each step. If a second step is not needed. piease put an "X" through the second box. '0) 0') Chemistry 3-20 2 Name: 2. FiEI in each box with the single major organic product of the indicated transformation or a starting material that wouid yield the indicated product. For full credit, your answer must use each reagent in a meaningful way. 0 o o ‘ NaOMe , a) ————————-——_> ’ MeOH O (N Molecular Formula: cquzoz 0MB 1.NaOMe,HOMe —————-——-—-—-———-—-> _ 2. H+ wkup Molecular Formula: CBH1203 1 MeO CuLt O MeO 2 —“_——."'"’——> H 2. H” wkup 3. HZNNHZ, KOH, heat 4. H3O‘” Molecular Formula: C7H120 OH 1 \ i _ v H, - + CH:3 Molecular Formula: CQH120 1'12 Chemistry 8-20 3 . Name: 3. Provide a complete synthesis of the dipeptide, giycylphenyiaianine, shown beiow. You may use any inorganic or organic reagents containing 8 or fewer carbons, along with the reagent DCC. You may, if you wish, use a Merrifield Resin, but it is not required for fuii credit. CZ? ' v i HYO iQchNZNl—hcr 3H2 MMHH Hwfii’” \m 291436?“ FA “AH/L“ A ” Doc, “HOW/HVOLOH /N (6:: V EVBWHECH (j ka0th> E giycyipheny a anine (as a racemic mixture) Chemistry 8-20 ' 4 Name: 4. Provide a muEtistep synthesis for the desired product from the indicated starting material. You may use any inorganic reagents and any organic reagents with five or fewer carbons. The best answer will require five or fewer steps. Starting material: ." 3H7 mm --=i-" O 0 H30 W03 i . ,4: N04 -. LL wit also be M, 0N??? fl Liv slut: M iii {vhf SleP 2% wlwl’ ml t“ in ms Pres: g C laiS/ih 0 _ g ii ll ‘7 k“ NoiOM .0?“ x ‘ sZ T7} “1%: /li\ 9Q a, .3 g)". _...-é._.‘__d.m_.g_.-...M....Md ‘- .. WM '42... v.4.lw.m..w_.w. a ... ~ ugwuw.._...,m.___:-_-..; .'.....::. Mug; ;. “3.1:; '. Chemistry 820 5 Name: 5. Provide a multistep synthesis for the desired product from the indicated starting material. You may use any organic or inorganic reagents. The best answer will require six or fewer steps. Starting material: A“OI‘\C‘0W£9VI‘T){ 2: 366A $23!? a I klfléfh 31/) o a swig. 1) 209:0?26 Wkgfie WW) MW: mg agar/Karate: if " W 2": '93 _. E Chemistry 8—20 6 Name: Be. It is observed that the cyclic ester A reacts more quickly with nucteophites that the acyclic ester B. Explain this observation using a frontier molecular orbital (FMO) argument. Note that B is shown in its most favorable conformation. e 0 % reacts more 0 of? quickly with nucleophtles . than (0) A In 8}W O 5‘31 Qt.) WWW "tn ,4) the, Cfirllb’hfi Cat?“ m Carbonv)’ C ff} lane toad? t3 l/IMGE U? @r avwlaf {MW/x v10 Soc/1A ewlaf Cm occur? Whiz, 8 is less “Mac/Mn poor“ 0 WM A: - 6b. Your lab partner proposes the synthesis of product "X" shown below. :4,th 002MB O 1. NaOMe, MeOH + 2. H wkup "X" (ii) In one to two sentences. explain to your tab partner why this synthetic route wilt not work. We, is 710+ 01 Van? au‘clr‘g N-vH MW WM Carbon?! Car bong,- Wraahm) We, is no cf WW3 step 'h) brim W mac/lilyl‘Di/t Th) COM/PlQ/lt’lbm} CLACl 'eiVIilll/OPIUM will Ave? W Sg‘afirmfl Male/flail . Chemistry 8-20 ,7 7. The Robinson Annuiation is a powerful method for constructing carbocyclic compounds. Please propose a complete curved arrow mechanism for the foilowing transformation: Name: Chemistry 3-20 8 Name: 8. Provide a complete curved arrow mechanism for ail steps in each of the following transformations: LDA - 1 o + I", :1 30 ffN R2“ 0—0 0 -' b) I: j/xA \A‘ LDA X H+ workup I :/ OH 7 i O I E i 1 l 1 l ...
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