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PracticeExam-5-B (Key)

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

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Unformatted text preview: Fifth Practice Exam B Chemistry 8-20 misses? Aitreai DO H Name: ID Number: Section TF: important Notes: 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 wilt not be graded. 'Anything written on the scratch page will not be graded. 3. You are allowed to use a set of molecuar models for this exam. _ Chemistry 8-20 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, please put an "X" through the second box. a) lie 63 a. Mattel. sz b) — m 1m 8% W .. 2- 215$” l ‘ 3. Mtg/NH; 9H5 DE )1 1. NotOifi CE 2- 265/- slung: WBF \ F’h I12 Chemistry 8-20 2 Name: 2. Fill in each box with the single major organic product of the indicated transformation or a starting material that would yield the indicated product. For fult credit, your answer must use each reagent in a meaningful way; Be sure to indicate stereochemistry if it is relevant! 1 1.1 equiv LDA, -78°C G) a ' ”\ejk 2% 3. H+ wkup 1. EtzcuLi ""‘—"‘—‘—>’ Molecular Formula: C17H24O O 1. Zn _ 2. EtBr \ OEt 5r 1 NaOMe 0‘ O —>— 25) _ 2. NaOH ( 3. H3O”, heat om“ Molecular Formula: Cal-£1203 i i l l i l i l l s l l l E i t g Molecular Formuta: CTHHOzBr i l a l E l l l t i I 12 l l l l Chemistry 8-20 3 Name: 3. Provide a muttistep synthesis for the desired product from the indicated starting material. You may use any inorganic reagents and any organic compounds containing 4 carbons or fewer. The correct answer will require six or fewer steps. Starting material: Cg 00; (1 W395 * it ‘ _ 01+Q£ M45 Fflfii‘tvb/gj O. - . lie/Jame HY“ # it \/‘\ _ - gqnoh-jcjf/o MQT “ l _.... Home“ my“ ES 30%i{r%v”le ‘1 ii a i Chemistry 8—20 4 ‘ Name: 4. Provide a complete curved arrow mechanism for the following transformation. 0 1) MezcuLi . —————-—)~- 2) H20. NaOH Chemistry 3-20 5 Name: 5. Provide a complete synthesis of the dipeptide. glycyialanine, shown below. You may start with amino acids protected in any way you wish and may use any organic or inorganic reagents. For full credit. use the Merrifield resin provided for solid-phase peptide synthesis. (A correct synthesis that does not use the resin will be awarded partial credit.) 7K0fLN (0% CILQ§ 3331?“ H o ”235° (5 \ z s; Lag/H (3* SF m "’2 :6 . x VP glycylalahine Chemistry 8—20 6. Provide a multistep synthesis for the desired pro uct from the indicated starting material. You may use any inorganic reagents and any organic reagents with Mor fewer carbons and no rings. The best answer will require five or fewer steps. (Hint: Be sure to work backwards from the product!) Starting material: any or anic compound [email protected] r fewer carbons m _ M“ ‘ \AAW '1 Jaww {53 . i (3 $ 0 1’12 Chemistry 8-20 ‘ 7 Name: 7. Provide a complete curved arrow mechanism for all steps in each of the following transformations: \\ i; M a) 8’" Q, Q {g Me20uLi H30*Workup M —> —-~“> . / OH /\ , /k//\/QO Ha. Me Me b) \ NaH H50+ Workup \ -——> —> (Hint: Look at it backwards...) l g .l i ii i l l l l I16 Chemistry 8—20 8 Name: 8. a) Provide a complete curved-arrow mechanism for the following multi-step transformation: 0 60 W INaOEt H30)? Workup NaOH H2504 I > >- EtO ’ OEt . , . . _ : s o} $35; ‘30”: ”10545 do ‘f’flose 2; 375a? i i3} A shame-t tried a srmaEar dooamoxyfiataon macho on {he foifowtng moieoale, but no reaction was observed. Why was this. deoarmyiafion not successful? _ H+ 6* OH 3- no reaction fix ...
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