30C_Winter04_Exam2_AKey

30C_Winter04_Exam2_AKey - Organic Chemistry 30C Winter 2004...

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Unformatted text preview: Organic Chemistry 30C Winter 2004 EXAM II, Page 1 Name 1. a) (25 points) Give the product(s) for the following reactions, assuming 1 equivalent of reagent is necessary unless specified otherwise (show each step, where applicable, to ensure max. credit if you are not sure of your final product): 1) Br2, FeBrs \ 4] 2HDAan ,/ 0 fQO \ OMe gr V A W \ Ky “7 ll 3 J (Wu H (9 z b) he, N02 1) Ac20, AICI3 C E U 2) MeZNH A 3) Fe, HCI 4) NaNO2, HCI i : l l ,0 5) CuCN // M9 Ma? N”: I Br \/ fil— 6 ’7 x. ""~ _/ \ € l / r0 L—‘a l‘ / ’0 7 l , '0 Z 3 9"? NMZ “fl; 0) ’O o 0 o 1T<fJMCI3 I —b- 2) SOCI2 3) AICI3 ] 0 d) Draw the HOMO and LUMO orbitals of the following diene: HOMO Organic Chemistry 30C Winter 2004 EXAM II, Page 2 Name 2. (25 points) Provide a step-by-step mechanism for the following reaction (no shortcuts! make sure to Show all intermediates and byproducts in addition to the correct arrow—pushing formalism): a) (15 points) Cl H4- + M (use it instead 94 of AiCI3 _in your CI mechanism) . 4 G) L , H H G; C\ CH5 0? Y A “‘3 (M H3C \I/ OH; —’~—v [\ 1 ] CH5 j: b) (10 points) Predict how the following reaction will proceed and explain with a short mechanism: N02 NO; 69 a; l EtONa Q i. a I E OH. 25 C OQN I t 05%) /fi)\r / .- 9 9 I ‘9 (—3 __..—-'\ w, 7%» @j fl?“ K 6’0 6; l ‘39 gm"? { [f 5—0 eég Show, 944.? mg \IU/ I- 0\}J/ A}? Qfié/Ffl w a fi’ Organic Chemistry 30C Winter 2004 EXAM II, Page 3 [a ( Name 3. (9.0 points) Devise a reasonable synthesis for the following compound from readily available reagents and the starting material provided: M: do no “invent” new reagents or reactions. There should be no more than 8-12 steps necessary in this synthesis, although longer ones may also be correct. You cannot use the minor product of a reaction, your route must proceed through major product pathways (i.e. can’t use ortho instead of para if the latter is major). (This problem is a bit longer. so if you write only 3-4 steps, you are probably wrong ( or I may have to give you an A+++).’ Br Br from , O (c n *4 Bfi‘Fgr} 91/ f 377/ (Wisoca) 7 \l\ ( ——o \I/ 2) Ala/00;, ML H6? rd H1 F F F Organic Chemistry 30C Winter 2004 EXAM II, Page 4 4. a) (15 points) Give the structures of the related fragment ions at m/z = 87 and 59 in the mass spectrum of t—BuOEt shown below: C‘HMO (mass of molecular ion: r15—1m-4175 / (flax 5v 100 SO— l (3 I \J“ 1. Relative Intensity 0) Cr I 3;; 1 00 90 so 70 so 50 40 relative intensity 30 20 10 1 50 1 60 170 1 80 1 90 200 210 220 230 240 250 260 m/z ...
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30C_Winter04_Exam2_AKey - Organic Chemistry 30C Winter 2004...

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