322bs06_e1_key

322bs06_e1_key - Organic Chemistry 322 DL Spring Semester...

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Unformatted text preview: Organic Chemistry 322 DL Spring Semester 2006 Exam 1 Wednesday, February 8, 2006 Name Gvaiflfi Initial of Last Name ‘3 T A ’3 Name 1 (24 pts) 2 ____._________————— (16 pts) 3 ____________._______ (6 pts) 4 ________________________ (6 pts) 5 (12 pts) 6 (12 pts) 7 ______________—_____ (12 pts) 8 (12 pts) 1. 0L '64 C R; Write the products of the following reactions or the reagent requrred for the transformation. Assume normal aqueous work-up (24 pts.) 9 e c. 1) (CH3)SCO K / ‘ :> 2) Cl-CHe—O-CHS \ W50 CV!) We“ “30(9)1%’ CTCQE) w: 0496/- 2. Choosing an appropriate alcohol or epoxige with up to four carbon atoms and bromobenzene as the sole carbon source’ prepare the product. (16 pts.) Bx" : (fH filmy <03 a + ” EM ‘ f O 1/0 ruffle . l @Mfiai (COMM 3. Draw the structures of phenol and aniline Be certain to clearly label them. (6 pts.) (we; Nl'NHL 0K 3 if?! inf/((69.1% ov~ 4. Label the following neutral compounds and ions: aromatic (A), non-aromatic (NA) or anti- aromatic (AA)Jas appropriate. (6 pts.) (2 h Ah (“Am/o 5. Use the polygon in a circle method to draw the molecular orbital energy levels for the cyclobutadiene. Label these bonding, non-bonding and anti-bonding. Use this M.O. energy level diagram to account for the instability of cyclobutadiene. (12 pts.) 6. Draw the n molecular orbitals for 1,3-butadiene. Arrange them in order of increasing energy. Label them bonding (B), non-bonding (NB), anti-bonding (AB), LUMO, or HOMO as appropriate. When 1,3-cyclohexadiene absorbs a quantum of light whose wavelength is 256 nm, show the n electron configuration of the excited state in terms of your MO diagram. (12 pts.) 7. Furan and Maleimide undergo a Die-\S' reaction. Z Draw a diagram in which the vertical axis is energy and the horizontal axis is the progress of the reactiorywhich are consistent with the experimental results below. _Be certain to label _ the starting material, the exo and endo adducts, thermodynamic and kinetic products on this diagram as appropriate. (12 pts.) 25°C - O / 0+ —H \ O Furan Maleimide Z 6%» we: {’3’ Secondary alcohols (e.g. cyclooctanol), are oxidized by chromic acid HZCrO4 to ketones (e.g. cyclooctanone). Draw the structure of the intermediate chromate ester formed in this reaction. Write the mechanism by which it breaks down to products. If cyclooctanol and cyclooctanol-d1 are oxidized with chromic acid in separate experiments under identical conditions, it is found that cyclooctanol-d1 is oxidized more slowly'than cyclooctanol by a factor of 4-5. What does this say about the mechanism? (12 pts.) ...
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322bs06_e1_key - Organic Chemistry 322 DL Spring Semester...

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