118BSpr11MT2KEY - 1. Reactions: (28 pts). Draw the...

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Unformatted text preview: 1. Reactions: (28 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemistry. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. H20, H2804 N E) N K heat Pd(OAc)2, PR3 ‘ B) MCI + $0 ——-———> 4. / (dummy) \ (rotten/sic) \ NBS, hv 3“ \ /\{l; \ D) l\ OWL Cl/ 1;,- E / H CH0 heat 5 \mCHO A 5 ANN. H CN /: (balm mtemk HBr, ROOR YR” H NH2 1) HNOg, H2804 gr“ /_ [3,. G) “fl’, \ ‘ 2) H2, NI 3) Br2 (excess) gr. 7 Reactions: (8 pts). Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemislry. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. ‘le 666“ HCI (cold) / __, / /\/\C| My)!” gt ) i I AICI3 (cat) 7‘? 'P’F Vocabulary: (18 pts) Fill in the blanks with the appropriate vocabulary word. If two bold words are given circle the correct one. Y Pl. each HQ lOéeni are resonance donators, but are generally deactivating towards electrophilic aromatic substitution. They are also OW a Z jbq Nx directors. A) B) A meta director is always / sometimes /@ an activating group. C) Tru / False A Diels-Alder works best with an electron-rich diene and an electron-poor dieneophile D) True / ‘33 Heat can close a conjugated diene to a cyclobutene and does so in a conrotory manner. E) A NH; -OH / -CH3 / -NHCOCH3 group on a benzene is the most activating towards electrophilic aromatic substitution. All these functional groups are Ov‘lho {gawk directors F) We generally get UV absorption by an organic molecule when we have at least 1 / @l 5 / 7/ 11 conjugated alkenes. We generally get visible color in an organic molecule when we have at least 1 / 2 / 5 / 7 /@conjugated alkenes G) Aromatic systems must be CyCl \‘C , (L , pla kg r and have an «I» 2 pi electrons. H) A reaction under r M461 ¥ng ml}, control gives the most stable product and generally occurs when the reaction is cold. 1) False Conjugated alkenes are more stable than non—conjugated alkenes. J) A conjugated system must have at least 2 l@ 6 / 10 parallel p—orbitals. These orbitals are always sometimes never alkenes OY)‘ u l. Mechanism: (13 pts.). Show detailed reaction mechanisms for the following reaction. Include all relevant resonance structures and the structure of the expected products. Br2, FGBr3 ——-—-—-—-—> ??? ® @ 6) ® <9 6 " " Q9 9 :- r’ r] BF~BrIfl€Br :2 [Br/Rr’Fefiigé') Br B F583 ., 5 5 @ A 3' CD gr CD Ea C901?“ r'BP‘Fe’ / H V H @j8 6; \q 6’ QEK/ He l1: J’FE’BW Gag 5. Synthesis: (14 pts) Show how you would carry out the following synthesis. Include the reagents you would need for each step and the structure of the intermediate products formed in each step. 0 A/"x m @ A q )A 3 2) H301~ / ls: @ \/\,o C) No Zna'tg) HCI O A CZ) Points {of any mocks? Synhu—Q gm KW l we 3 Cl \ 0" Cl)\/ G) l 6. Identification: (6 pts) Label each compound as aromatic, non-aromatic, or anti aromatic. O N (9 / I \j T > / . I N / N / Aromqfic hon womb} g worm he 0m“ ammaifi‘c 4Y0 Wm M Mali: 7. Nomenclature: (8pts.) Provide the systematic names or structure ofeach of the following compounds include E/Z Where relevant. OCH3 @\ I'Me‘l’koxy— 3— PmPyl behaem . A) m- Prowl aulsole (glitzy-’1 ¥’dib"0mo - S ‘ChM/l - Z-Vvliiky/VWHQ‘ l, 3,6 ‘ triep‘e B) Br o) 7i brow Zisatwyl 9mm! Li-bvumo’ 7—- (fishy! elk/I loan 2 {n ol OH O /\/ D) p-propoxychlorobenzene @ 19k 9‘ C,“ 2)::W Cl 8. Reactivity: (8 pts) Circle the carbon(s) on each molecule that is/are most likely to undergo reaction in an electrophilic aromatic substitution reaction. OCH3 COOH O : ‘N/U\ : Br B H N02 r ZPiE \39P moiewil. 9. Spectroscopy: (20 pts.) The unknown compound A (C15H220) gives the following proton and carbon NMR spectra. Significant IR peaks were also observed. 200 u 150 100 50 0 IR: 3324 (sharp), 3034, 2957, 2253, 1592, 1210, 792, 702, and fingerprint cm“. ...
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118BSpr11MT2KEY - 1. Reactions: (28 pts). Draw the...

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