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14C_s10_finalB_key

14C_s10_finalB_key - Chemistry 14C Spring 2010 Final Exam...

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Chemistry 14C Spring 2010 Final Exam Part B Solutions Page 1 Statistics : High score, average and low score will be posted on the course web site after exam grading is complete. The exam is ready to be picked up when these numbers are posted. A note about exam keys : The answers presented here may be significantly longer than expected from a student taking the exam. An exam key serves not only to reveal what was expected, but to instruct you as well. To see the final course grade cutoffs, consult the grading scale on the Chem 14C course web page. 1. (a) Thalidomide has 16 sp 2 atoms. (b) Thalidomide has 16 conjugated atoms. (c) 16 atoms of thalidomide are involved in partial or full pi bonds. (d) The largest group of atoms that always lie in the same plane contains 16 atoms. 2. Cannot determine Color cannot be determined based only on the number of conjugated atoms . 3. N N O O O H O H Thalidomide has only one sp 3 stereocenter . 4. Including the molecule drawn in question 3, thalidomide has two stereoisomers. Of these, two are enantiomers of other molecules and zero are diastereomers of other molecules. 5. N N O O O H O The most significant resonance contributor has the negative formal charge on oxygen (more electronegative than carbon) . 6. p K a = 16. The electron-withdrawing inductive effect of the nitrogen atom (absent in acetone) provides more stability for the conjugate base, making it more stable, and (compared to acetone) H a more acidic.
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