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30C_W05_final_AK

30C_W05_final_AK - Organic Chemistry 30C Winter 2005 K...

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Unformatted text preview: Organic Chemistry 30C Winter 2005 K , FINAL EXAM, Page 1 w (W 2/ Name 1. a) (15 points) Give the number of n: electrons and determine whether the following compounds should have aromatic, antiaromatic, or non—aromatic character (i .e. a degree of those properties): . _ aw rtelectrons: 20> ___o___ ( 27-5357 Character: w/CQW . 6216/“ v (gt/{Wk M M. ALI/51a b) (7 points) Draw the relative energies of the molecular orbitals of the Wmmon shown below. Indicate in which MO’s the electrons are located and predict its stability: EA —— E: 4.. @(LVQ (OI it méa/Aa, c) (8 points) Draw a transition state approach that describes clearly the stereochemical outcome of the following reaction: M Transition state geometry: w J 969 9‘41 Organic Chemistry 30C Winter 2005 k FINAL EXAM, Page 2 05/ t” . 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): 0 ) (9H 1 heat MeOW 2) H+, heat \9 O M (0m 0 14K . ’7 Off b) \ 0H \l H H O 0 \Jk/ 1) MeNH2 (1 eq) \ / 2) NaBH4 \ '0 C) 65 /7 m f w H52, M, Br 1) NaN3 /‘\ 2) H2, Pd-C \ , ———*> I 3) 2 eq. CH20, [ q‘ _ CH3 2eq.NaBH30N \/ ' CH 2; ‘> 7 \ H eat fl : ’ N L32“) 2?: j "I O U \ N H 1) w, H /\ 2) CH2=CH—CH2Br, K v— , ) then H3O+ (:5 3) EtONa, /l\\‘ t) heat 00 o 1‘ 0 ‘ , [w w a a? 0 e) \ OH 1) FCC (excess) ———————> OH 2) NaOEt, heat 3)MeZCuLi \/ o \7 0 ' l ll CHO v W ,, \t 9 / / ‘\/ V \T; q H Name Organic Chemistry 30C Winter 2005 I, FINAL EXAM, Page 3 / 9/ 3. a) (30 points) Give the product of the following reactions, assuming 1 equivalent of reagent is used unless specified otherwise (show each step, where applicable, to ensure max. credit if you are not sure of your final product): (91,) (9 n A a) ‘25 ’7 \\D/’ \i) 0 H CI / wz/ PM, 1) KOH _\ 2) Fe, HCI ( / l ——-> 3) NaNOz, HCI 4) HBF4, then heat N02 F b) OZN N02 1) xs Et2NH / NHL ____> / F F 2) H2, Pd-C ) \ l / \ 0) OMe 1) Br2, FeBr3 2) LDA, We) «7k / O \ /\\ V d’ <19 V ./ A?) heat ————> \ / \ / e) O 1) /\f EtOzC> EtONa / U EtO c 2) NaOH, H20 H00 C W 2 3) H+, H20, flew— )1 540 LC Egg ZcWO (7 Organic Chemistry 30C Winter 2005 FINAL EXAM, Page 4 _ Wé‘é/ Name 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) (’0 EtONa, heat 0 O 2. ——————» (7“ $03 OEt EL" V” \ l b) (15 points) -1 O‘“/-——\ NMe2 Organic Chemistry 30C Winter 2005 FINAL EXAM, PageS fiflé W @' Name 5. (30 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 speczfically 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) Ph 0 / M; a a ‘ b) (15 points) OH O @03, v We 549? 0 fl is f « » Why/z «b O 0H Organic Chemistry 30C Winter 2005 FINAL EXAM, Page 6 6. (30 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) ,eyo/yaagfm b) (15 points) N02 HO Cl Organic Chemistry 30C Winter 2005 a , FINAL EXAM, Page 7 we/ (67% Name 7. (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. ...
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