30C_Spring07_Final_Exam_AK

30C_Spring07_Final_Exam_AK - I Organic Chemistry 30C Spring...

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Unformatted text preview: I Organic Chemistry 30C Spring 2007 ,. ./ n FINAL EXAM, Page] , MW 6/ Name ‘ a) (10 points) Give the number of 3': electrons and determine whether the following compounds 1. should have aromatic, antiaromatic, or non-aromatic character (i.e. a degree of those properties): N‘”\ N N \ (OJN / .. \ / l T T \ I /BCH3 N/ H \ .N. / /N N/ It electrons: £2 _ ‘ _L__¢’ . {ml MM) ’ Character: bet/Mam M'Q/Mflo ' w“ M5“ - b) (9 points) Draw the relative energies of the molecular orbitals of the cyclopentadienyl cation shown below. Indicate in which MO’s the electrons are located and predict its stability: / b v. f 4» «‘2’ macaw“ ,. We (Pt :“2 5w Q‘fi c) (6 points) Histamine, an important chemical in our bodies, functions as a neurotransmitter and a potent vasodilator. It is the agent that causes many symptoms of the common cold (hence antihistamin drugs being sold over the counter). Explain and rank the basicity of each nitrogen in histamine: 1)NH21 3>N: w g,“ WI) Organic Chemistry 30C Spring 2007 FINAL EXAM, Page 2 Name 2. a) (30 points) Give the product of the following reactions (show each step, Where applicable, to ensure max. credit if you are not sure of your final product): 6555} a) O O LDA _ I /\000Et ———+ (\V» a )/ 0H C LiA|H4 H30+ ———> }\V ——-—> b) v , Cl ,9 H7 HN03, H2804 1) NH3 —> —-—> \ v 2) Fe, HCI { / l NS? 2/, rim/1:, (9)”; C H20, A CrO3, {1 XS CU2 ‘/‘ H2804 ——-———> —————> \T/ ( ‘1 ,2 c) ‘ , N H: C Z {\x LiAIH4 NaCN / (2 eq) /I —______> , @CN EtOH C {t ' r , N ‘J _ r I“ “7 [NH ” 2 " A920 heat ( , \ ,-, 3.621,, O N3, NaNOQ, HCI i (2 eq.) ————> 1) heat MGOW ————> ’ \ \ 2) H“, heat \ / / 0 t7 ,iP‘, l C/ N H9“: c») Mel T- (XS) 1—, —> ($92 J, 3 ‘A 7., (f 9L“ m 7' r“ V HQC=CH-COEt, /\/Ll\\ heat Organic Chemistry 30C Spring 2007 4 , . FINAL EXAM, Page 3 ‘ 1, 49/44 “6/ a) Name 2 3. a) (30 points) Give the product of the following reactions (show each step, where applicable, to ensure max. credit if you are not sure of your final product): 3:; a) H H OH HO § \J (C e 1) NaH, B“ \./r ———————> l I I 2 heat \ 3) cold, dilute V Hgso4 ——"7 b) 1) KCN, HCI 2) LiAIH4 ‘ -—-——> 3) NaNOQ, HCI ‘ 4) PhMgBr \/ 1) NaOEt, . BrCH CH CH EtOZCVCOZEt 2 2 3 2) NaOEt, Etl 3) NaOH, H20 4) H30+, heat Br ©/ONa 1) 2) H2, Pd/C ————-—> 3) NaNOQ, HCI N02 4) CuCN CI Organic Chemistry 30C Spring 2007 FINAL EXAM, Page4 .‘ flew/05% I Name V 4. (25 points) Provide a step-by-step mechanism for the following reaction (no shortcutsl). Make sure to show all intermediates and byproducts in addition to the correct arrow—pushing formalism): a) (10 points) OCHZCH=CH2 OH heat CH20H=CH2 l ————> 4,, 4 H \ AG) 5 V” H C \ ti ll; l7 l l} // /L|\ H v , fl Fifi — *~ if 2 M. ~22 (i, (1H [wét \ b) (15 points) do 0 O J EtONa, heat H r EtOH //’/ V 1.3 0 HR E75” ‘ Lew/‘4 o _ wet ./ C" / ~ - _; by A (1;- “0H Name Organic Chemistry 30C Spring 2007 ~ / , / , FINAL EXAM, Page 5 f Zz‘g/ 5. (25 points) Devise a reasonable synthesis for the following compound from readily available reagents and the starting material provided: Note: do no “invent” new reagents or reactions. Use only those specifically taught in class. There should not be more than 10 steps necessary in these syntheses, although longer ones may also be correct. a) (15 points) CI Cl 45 I, OH l’ ‘f l l M oz - fl/ “’ . V H (f l é / Mr \ (A /.’»€/fltcf@/ b) (10 points) Organic Chemistry 30C Spring 2007 FINAL EXAM, Page 6 /7l/ri%r/ / Name 6. (25 points) Devise a reasonable synthesis for the following compound from readily available reagents and the starting material provided: Note: do no “invent” new reagents or reactions. Use only those specifically taught in class. There should not be more than IO steps necessary in these syntheses, although longer ones may also be correct. a) (10 points) I Organic Chemistry 30C Spring 2007 (A , r I r FINAL EXAM, Page 7 , , nf/U‘C/ Name / 7. (20 points) Devise a reasonable synthesis for the following compound from readily available reagents and the starting material provided: (mescaline is the halucinogenic substance from the peyote cactus) NH2 CHO TU ——> M? ,u 0M9 MeO OMe 1w: a. 0“ OMe "’ vanillin mescaline l @% I 23/ : {I “2%”? _ I} \a \ , HwMeW @‘W/ f 24% C (72,532, l ’ /‘~ . A U «A ,~\ (/11 W J y W (.4 b a *7 v : (p51 My / ) [\AZI/ /L\‘ H CC Nil/H / \ / 1 I; C]? ,__,*§_7 :5 l \ / v \ '1 ' s r 1 Ad (/1 " I \ (,1 7L 5/“ L, /J\(\ cg) 61ft Organic Chemistry 30C Spring 2007 w _ FINAL EXAM, Page 8 r MW {47 ' Name ' / 8. a) (10 points) Given the Fischer representation of D—gulose, draw its structure in the pyranose form in both chair and Haworth representations: CH0 P, [Ch/(2 1],"! b) (10 points) Explain with a sketch and a brief explanation why the chlorine substituent in the following compound prefers to be in the axial position: i ,' / ~ 7‘: i I, , A», / 1"“: 4 Organic Chemistry 30C Spring 2007 FINAL EXAM, Page 9 EXTRA CREDITS: Extra Credit 1. (10 points) In a procedure published in the Journal of Organic Chemistry 1998, 63, 9037—9044, the following clever set of reactions was used to prepare a furanoside. Show a mechanism for the second step (acidic hydrolysis) which accounts for why the oc—anomer is formed preferentially. Note: this problem is not as hard as it looks! 1) 03, A00 H then Megs O —> H AcO a 2) H+, H20 H OH AcO H Organic Chemistry 30C Spring 2007 FINAL EXAM, Page 10 Extra Credit 2. (10 points) Write the mechanism for the second step of the following reaction: ~ a‘r/v"\\ H - H H M 1)CH2=CHLi o / . , then H30+ , Q 5 M60 /\0 2) KOtBu Mao , / A La ' 5;, VIC/4% / \L/ C) "J’flv ~~~~ pig/f) 4L, / // (/79/5 ( (1' i ,,,,,,,,, (I A H ,. t7 AEV) ...,/"' ////M v. ...
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This note was uploaded on 05/02/2008 for the course CHEM 30C taught by Professor Kwon during the Spring '08 term at UCLA.

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30C_Spring07_Final_Exam_AK - I Organic Chemistry 30C Spring...

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