322bf03_e1_key - Fall 2003 Organic Chemistry 322bL\x Exam 1...

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Unformatted text preview: Fall 2003 Organic Chemistry 322bL \x September 22, 2003 Exam 1 ’ V 11/ \ \A I; Name Initial of Last Name ‘::| T.A.’s Name 1. (26 pts) 2. (1 0 pts) 3. (8 pts) 4. (12 pts) 5. (10 pts) 6._______________._ (12 pts) 7-____________________ (5 pts) 8. (15 pts) 9. (5 pts) (msfiJ Total 1. Write the products of the following reactions. Assume normal work-up. (26 .- - OCH3 Li ow} —————> .- a' liq. NH3, EtOH l \ H3 6 CUM N02 1)KMnO4, OH ,A \ (NO?! b- 2) H30‘9 l / ’75., 0 C. ©:> N-Br Eel. \r {:ENH A l l 91; 0 it H 0 ll large excess d. Br2/H20 aV\ \xfiw / O H2NNH2 /\/ CH2-CH3 ‘_—.* .. '/ \ KOH high bonling solvent \ e. B A Q/ CH2-CH20H E\ (O f' O MHZ / H ‘A H2N if \ I , if [I @N H2?P-O-I|3-O H2 N - . 0 Ho OH MIN» 1; 9. © Bra/CCI4 —> dark 25°C N U R X S? ‘ C-OCH3 room temperatute h. :> + E 0 _ fiD-OCH3 diethyl ether lug O M i. CHa'EOC02CH3 €13??? n . i 0.“ J. AGO/LG" t4 + Q<27CH-CH3 ______> O k. 0” + CH3'CO2CH3 —'——* I. CH3 excess m' Br + (CH3'CH2)2CULi ————-—> Etzo Br 2. Given bromobenzene/O , ethylene oxide HZWCHZ , diethyl ether, 0 CH3 \ . . tetrahydrofuran 1 OS , pyridine I N/ , and any Inorganic reagents you need prepare i (10 pts) 2 H 3. Label the following unsaturated cyclic neutral and ionic species aromatic (A), if appropriate. 80% 20% at -80°C law/kc“ 20% 80% at 40°C We” Ml ‘M W! ‘ 7V (_, Draw a diagram to account for these results in which the vertical axis is free energy and the horizontal axis the progress of the reaction. Draw the intermediate(s). Label the kinetic and the thermodynamic product distributions. (12 pts.) (9) . fi/v fl " Hg") l4 (5‘, \,L H K—sgyf-ffi NH-E-CHs I O c I n 5. Given acetanillde (j and any inorganic reagents you need, speCIfIcaily prepare ortho nitroaniline. (10 pts.) 6. Given benzene, and succinic anhydride CEO and any inorganic reagents you need; 0 O prepare oc-tetralone Cb This synthesis relies on two Ff u ‘ -C d ? reactions. (12 pts.) 0 o y /“ Am .r 'i _ > it. ©MCOZW A 0 31 mom/owefl Amy) Ha WW POL} / / was, we‘d 7. Circle the isoprene units in trans-retinal. (5 pts.) 8. Draw the 1r molecular orbitals of 1,3-butadiene. Arrange them in order of increasing energy. Label these HOMO, and LUMO as appropriate. Use a diagram to show what happens when 1,3-butadiene absorbs a quantum of electromagnetic energy whose wavelength is 217 nm. Contruct a diagram to show how this happens. (15 pts.) 9. Arrange the following free radicals in order of increasing stability. (5 pts.) Ti“ CHy? ‘ CH3 =. /\C'H2 CHyCHg ...
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