14D_f08_e01_key

14D_f08_e01_key - C h e m is t r y 1 4 D F a ll 2 0 0 8 E x...

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Chemistry 14D Fall 2008 Exam 1 Solutions Revised 11/04/08 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. Some questions have more than one answer, even though only one answer is listed here. To see the projected course grade cutoffs, consult the grading scale on the Chemistry 14D course web page. 1. (b) . ..is mostly S , rarely R (f) . ..cannot be determined is also acceptable. Consider a case where an S N 2 reaction destroys a stereocenter because the nucleophile is the same as one of the existing attachments to the carbon that is undergoing substitution. 2. σ * orbital 3. Steric hindrance caused by the leaving group after its departure but incomplete migration away from the carbocation . 4. Polar, aprotic, an amide 5. CH 3 CH 2 O - 6. CF 3 SO 3 - 7. Many answers are possible, for example: 8. If S N 2 and S N 1 rates both increase, write ‘increase.’ If S N 2 and S N 1 rates both decrease, write ‘decrease.’ If S N 2 and S N 1 rates are both unchanged, write ‘unchanged.’ Otherwise write ‘cannot determine.’ (a) Increases (b) Cannot determine Increases for S N 2 but no change for S N 1 . (c) Cannot determine
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This note was uploaded on 11/23/2009 for the course CHEM 14D taught by Professor Hardinger during the Fall '08 term at UCLA.

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14D_f08_e01_key - C h e m is t r y 1 4 D F a ll 2 0 0 8 E x...

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