OchemB Exam 1 - Organic Chemistry 322 bL Fall 2004 Name...

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Unformatted text preview: Organic Chemistry 322 bL Fall 2004 Name Exam 1, September 20, 2004 G incl; ”5/ Total Initial of Last Name ‘:‘ T.A.’s Name 10. (20 pts) (8 91$) (10 pts) (10 pis) (10 p15) (10 pts) (10 pie) (10 pts) (6 P15) (6 p15) Write the products of the following reactions: (20 p15.) 25°C, dark ”0 tang/cm4 Mo vezosfiw / d) 9'." l \ \ \ \ CHQOH H Cr03C|e \/ ——————> 0/0043 U m: f01.:uml EKG %< Fink) com f) 02H HNo3 ————> H2804 M07, M 9) HZCHS KMnO4/OHG NO N02 _____, z. A i) G + CHs-CHg-CH2-CI JE» Q/L j) Zn/Hg CH -CH —————-> _ 2 3 HCI toluene i _ 2. Specify reagents and conditions used to achieve these regioselective transformations: (8 pts.) Wig WW ngéi/ 3%» r r / Q38 MOLE:- gig" @ \ 3. Given bromobenzene and any organic compounds which contain up to tour carbon atoms prepare: (10 pts.) / 9 1> " \/ on of mm D) 4. Label the following cyclic species aromatic (Ar) or anti-aromatic (Aa) as appropriate: (10 pts.) lm/x/ 5. Use the polygon / circle method to construct an energy diagram of the n-molecular orbitals of the cyclopentadienide anion CsHse. Put the n-electrons in these orbitals. Label the orbitals bonding, anti-bonding or non-bonding as appropriate. (10 pts.) if the heat of hydrogenation of cyclohexene is -120 kJ, what might you reasonably expect for the heat of hydrogenation of benzene? If the actual experimental value of the heat of hydrogenation is —208 kJ/mol, what does this mean? Use structures to account for this result. (10 pts.) L!» 25M $X~lloxj W‘ECO K: ' Wm mm WW g+ M%l§ZKJ}kV‘W% o/QQHEE In no more than twelve words account for the following 0-0 bond lengths: (10 pts.) CHs-T-CHs CHaTCH=CH2 HQC=CHTCH=CH2 1.54A 1.50/1 1.46/3. 2. 1.. ll) 1’ . _. CrC . XMAS (“24W W‘NG’ $«C2 w, 8. Azulene has a permanent dipole moment. Draw resonance structures which account for this dipole moment. Draw the dipole moment. (10 [email protected] G) C as?” 9. B-Carotene absorbs light at 497 nm. Is a quantum of such light higher or lower in energy thanllightfa‘quantum whose wavelength is 220 nm? Write an expression for the relationship of energy to wavelength. (6 pts.) W \[email protected] C/ ”5,. ll 5/ E E ’ 1o. From ethyl magnesium bromide and what ester can you prepare 3- -pentanol In one step plus work up} Write the structure of the ester. (6 pts ) ‘31 Hrs ’09: flirt :Oa—l ...
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