Exam3_Key

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C3443

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Chemistry

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Oct 30, 2023

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LAST name: K@‘)\ First letter of your last name First name: CuID: Organic Chemistry | CHEM C3443 Exam 3 Fall 2012 November 8 On my honor, | have not given or received help on this examination. Signature Page 2: 122 Page 3: 120 Page 4. ne Page 5: n2 Page 6: 4 Page 7: 16 Total: -This document contains a total of 7 pages. CHECK that you have all in this packet. -Write your name on every page. -In addition to this document, all you need is a pencil (or a pen) and an eraser. -ALL OTHER ITEMS SHOULD BE TURNED OFF AND PUT AWAY. -Write your answers clearly and concisely on the space provided. -Use the blank pages to work through the problems, but they will not be graded. -Raise your hand to request scratch paper. -You will not receive a periodic table since it is not needed Good Luck!!!
Name: 1. 22 pts. Draw the structure of the product(s) for the reactions below. Draw dashes and wedges where necessary. 4 \ J - ~ (XS)KMnO, ! {0 —_— g\/ : " W L J N Li/NDs Ul HE—-—O _— " L ] 0 1) 2 eq. BHy N 2) 2eq. H;,0, ¥ eaants NaOH/H,0 ol L ) ; (XS) HCI H%O —_— ol a pis. this pg
. o . . FUE PN i . : RS TS LR B S U RN . FE i AR TR ISN f . - . : C gy et S . ; "V " . i by T : T 7 RN 1 ' [ 1 K . ] ! [T . . . L A Lo . : ) : ) . : N - - Ty FENGPAN ; f . ] / - N \ L\‘ AR - - . Yoy v ! ST AN P " t .. - ' i s - 3 R ¢ * Ve . P r 1 i { Y T Ey - L L . : - . et . il E . . s il . T . - Vi . - . i " ' . .- ' [N ) v R L L Y e i . 0! . { L BX . n . i \!.'. 1\"4.; el } /\ K P
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Name: 2. 20 pts. Fill in the chemical structure in the empty boxes below. Compounds A, B, and D are isomers with a molecular formula of CeH1s. Note: There is no need to draw dashes and wedges where chiral centers are formed. A E 1. 0sOy4 i o\ 2.NaHSO4/H,0 OOl pisi g e U 3. NalOy/H,0 ¢HZO, cat H* OH oy iH;,SOa. Hy0, A T T i i B F ) o] 1.03 | Ol 2.Zn/H40* d v KAy _— ¢KOH Pl YA D KMnO, o —_— W 0 NS i pts. this pg
Name: 3. 16 pts. The oxymercuration-demercuration of (1Z,52)-cycloocta-1,5-diene yields the bicyclic ethers shown below (a and b). Draw a suitable mechanism that accounts for the formation of compound a ONLY. 1) 2 eq. Hg(OAc), O HZOITHF : ® ( 2)2eq. NaBH,, pts. this pg
Name: 4. 10 pts. The bromination of compound a yields compound b almost exclusively. Compound c is not observed. Draw a suitable mechanism that accounts for the formation of compound a. OoH OH Brp Not: —_— Br Me " rhE H Py tre a b e Ve c Br % [GF) ol oh 2 pts. In three sentences or less, explain why compound ¢ is not formed (you may use drawings in your answer). Tha Bowabion 4 & vorld inoboe e stk of 88 4o HHae Bromoviawa low such Puat: gx'ék However, tis atlack is sherreal :514""40‘ 1 byt aleohol- —fl«erefecq‘ o+ c,vean- %Dyen. pis. this pg.
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- I . EEE R Tole * * . - o . IAEREATIN . . . ~ . ~ . - . ~ e . (NN - Nt T R . . PR 4 = R [N J T 01 [ 2 rean v i A - e i v P SN - T - ;o PN 1 P RN [ PR ¥ R Wl :,;-f.'_- | .
Name: Syntheses: for the problems below, the number of arrows are not indicative of the number of steps required for the synthesis. Choose the path with the least number of steps for maximum credit. 5a. 7 pts. Using acetylene (C;H.) as your only source of carbon, propose the synthesis of hexane-2,5-dione. You can use acetylene to make other compounds you may need. o e H———H \“/\)l\ o hexane-2,5-dione [ 2 ;, S , 5b. 7 pts. Starting from acetylene, propose the synthesis of compound a. o = oy a Lindwr= Pd/cacoy \1191/ Lind lar Y, H ’_/03 D; :p 2. Za, 4367 pls. this pg TF
Name:_ 5c. 8 pts. Using any alkyl halides containing only one carbon and acetylene (C;H;) as your only sources of carbon, propose the synthesis of the products below. You can use acetylene to make any compounds you may need. Cl, w V/*D + (15,2R)- enantiomer (1R25) Note: simply show the synthetic path to make one of the above enantiomers. 1 el CH;T Nante =g & e Nod) By ® @ > - S =W —= 5d. 8 pts. =X etz r— ;&) = NNE, =9N = 1P pts. this pg
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