14D_f11_finalA_key

14D_f11_finalA_key - Chemistry 14D Fall 2011 Final Part A...

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Chemistry 14D Fall 2011 Final Part A 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 (or mailed out if you gave an envelope) when these numbers are posted. A note about exam keys : The answers presented here are usually 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 14D course web page. 1. Accept nucleophile at carbon. An ester loses resonance upon nucleophilic attack but a ketone does not, so the nucleophile preferentially attacks the ketone. Hydroxide ion is the strongest nucleophile present. O P O O O O O O P O O O O OH O OH Accept electrophile at oxygen. A protonated ester has two significant resonance contributors whereas a protonated ketone has only one, so the ester is protonated in preference to the ketone. Hydronium ion is the strongest acid present. O
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14D_f11_finalA_key - Chemistry 14D Fall 2011 Final Part A...

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