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exam4 - NAME IL'IJ!l first last Page 1 ofti CHEMISTRY 2211...

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Unformatted text preview: NAME IL'IJ'!l first last. Page 1 ofti CHEMISTRY 2211 EXAM '4 April 25. 261113 Be sure to read each question earefitiiy. Partial credit will be assigned where appropriate. balm” To receive full etedit you must answer the question completely. Relax and good luelcii l. 1. {Hi pts} Classify each of the following moleeules as aromatic, anti-aromatic, or oonuaromatie: 2. I” K i? x I 3 — ‘3 A ‘— £3.) 4. Amwth-L'h‘: 1;. Anti—I —prr‘r}f'-oa.+l(_,, HDA‘fir-t‘pfl‘lhfifi. 5. a. l \ ’N ” Eta 7’ _ N1 — f H s. Afloat-i e. flax-ls erfitrem'fia 9. . Hi. 2. [5 pts} The speeifle rotation, [can , of (S]-alanioe 1s +3.5“. Caleulate the observed rotation, or, of a 5J1] g sample of (S]~alanine that has been dissolved in I mL of ethanol and plaeed in a sample eellwhieh has a path length of 15 em. You must ll. show all of your work in detail to receive credit for this problem. T _I ex . r I. . In, LS2" lo. ' e 5'91j' i_'“; g Total: c; ~ —' - - . .D = A IMLEiUH J/e'» L Is ' I .: h. i I _ _||_,_.L _= l c; d m A}? I 417' t' or. If --, ' I Set - J— r“ _._ \B 1.; '7 __ — _ I M _ {£3_r}‘j \ _." _,_, If i Ilhl'flj.lr_1:\le fish} L_—__ Page 2 of 8 3. [3 pts} Provide all of the most likely products resulting from the addition of 1 equivalent of HBr to the following compound: In order to receive full eredit for this: rohlem. rou must rovide the structure of each final roduet as well as the structure of the s eeifie intermediate that leade to eaeh Eroduet. Your answers do not need to indieate an s eeifie stereoehemistn'. Be etear and organized in your arrangement of your answers. [3r {B Vie-Eb 3 “new if) Haws-J It Gr 6% —._Huh} --...____’_,_.r-=-"" I“ Pogo 3 of3 4. {19 pts} Provide the appropriate names for the following compounds: name: {1 3,3145}. 2-hrom o-1-terI-bo1yI-4-ma Hflyloydo hexane Page 4 of 8 IS. [it] pts} Complete the following electrophiiic aromatic substitution reaction schemes by adding the appropriate reagentlfs} antifor intermediatets}: T. [It] pts} Complete the following reaction schemes by adding the appropriate starting material. reageott's] amflor producttsj. Make sure to indicate the proper stereochemislry when necessary: Page 5 mfg Br; ———p-— %l\/ - ‘I equwalent B. {12 pts} Assign the appropriate R and S designations tn the chirality centers found in the fullnwing compounds. You must clearlv indicate spur answer for each sterencentsr. Be careful and make sure to double check ynur wnrk. Isms}: 5 fl HDICHO Br : BPIzCHg CH2CH3 II“ a (in. Ta Fags G of 3 9. [11} pts) Write a series of steps to accomplish the following synthetic transformation. You must provide all appropriate reagents and intermediates for your synthesis. fig reaction mechanisms are neeessarv to answer this nestion. Er NH; Q a j r I? Er Q a Y em“ a “a “1 Petr; r . HL Pam *_J/’\ .r Fe, H35? {H In uhHSD' ' v 51" W Page 7’ Offl 1|]. {1 I pts} Complete the fallnwing reactiun schemes by adding the apprupriate pruductlfis). Make 51: re to indicate the praper stereochemistn' when neucssary. Clearlv indicate whether or not each rodllttll'l rnduct mixture is u ticallv active rovide nnh’ lune answer gar Jamal: £1"; r99": maxi—f Raflem: Mixture Page 3 or 3 11. {It} pts) Provide a complete, detailed and stepwise mechanism for the following reaction. In order to receive full credit you must show _a_ll electron movement. Be sure fllflt vou clearlv indicate how all of the relevant reactive s eeiesa'intermediates are generated: SD3H 303 G D G D H q A o H I1 5 / + “*G—g—DH :‘e seek + est—claim: 0 “L199?” D EB m l' | e'x If, Emmi fl \ + '95 ’4’ | h 5a.. a; 4/ ROM 19—— t\ III DH .I 2.) fl DE: fiH'U'fiI-L IIELE r X75) n flH/l J Ofigwo _DF|SI_—OH C) re!— I ,II A"! I'm-moo.- Cfl-m L‘s-c drawn E 503“ or) ...
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