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14D_w09_finalB_key

14D_w09_finalB_key - C h e m is t r y 1 4 D W in t e r 2 0...

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Chemistry 14D Winter 2009 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. Some questions have more than one answer, even though only one answer may be listed here. To see the final course grade cutoffs, consult the grading scale on the Chemistry 14D course web page. 1. Triflate is an excellent leaving group but poor nucleophile due to resonance (or electron delocalization) and inductive effects . 2. 3. (a) Rate is slower. NaSPh is a poorer nucleophile than NaSCH 3 due to benzene ring resonance delocalization of the sulfur’s electron density . (b) Rate is slower. Bromide ion is a poorer leaving group than triflate due to the lack of resonance and inductive stabilization in Br - . (c) Rate is slower. A tert-butyl group causes more steric hindrance than a methyl group .
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