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14D_f08_e02_key - Chemistry 14D Fall 2008 Exam 2 Solutions...

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Chemistry 14D Fall 2008 Exam 2 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 is listed here. To see the projected course grade cutoffs, consult the grading scale on the Chemistry 14D course web page. 1. E2: X No strong base is present . S N 2: X No good nucleophile is present . E1: Ph CH 3 CH 2 CH 3 H 3 C The other alkene isomer is less stable. S N 1: Ph CH 3 CH 2 CH 3 CH 3 H 3 CO Inversion is favored over retention . 2. Ph CH 3 CH 2 CH 3 I H 3 C Ph H HOCH 3 H 3 C CH 2 CH 3 H 3 C Ph CH 3 CH 2 CH 3 H 3 C 3. (a) BH 3 (b) H 3 O + 4. The starting material alcohol (abbreviated here as ROH) is a stronger base than bisulfate ion ( - OSO 3 H), so ROH is the base of choice. Water is not among the reactants nor is it generated in the course of the mechanism, so it cannot be used at any point. O
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14D_f08_e02_key - Chemistry 14D Fall 2008 Exam 2 Solutions...

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