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

Info icon This preview shows pages 1–8. Sign up to view the full content.

View Full Document Right Arrow Icon
Image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 2
Image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 4
Image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 6
Image of page 7

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 8
This is the end of the preview. Sign up to access the rest of the document.

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.) ...
View Full Document

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern