14D_w11_e02_key

14D_w11_e02_key - Chemistry 14D Winter 2011 Exam 2...

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Chemistry 14D Winter 2011 Exam 2 Solutions Revised 02/23/11 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 projected course grade cutoffs, consult the grading scale on the Chem 14D course web page. 1. C C HCl Cl H In the first mechanism step, protonation by HCl occurs to give the more stable carbocation. 2. Yes The hydrogen atom of HCl becomes bonded to the end of the alkyne which has the most number of hydrogens to begin with . 3. Cl 2 Strong base Cl Cl Cl 4. H 3 C H 3 C OH H 2 O H H 3 C H 3 C H 3 C OH 2 H 3 C HO H OH 2 5. K eq > 1 A keto tautomer is often more stable than the corresponding enol, unless the enol is stabilized by conjugation, intramolecular hydrogen bonding, or aromaticity
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14D_w11_e02_key - Chemistry 14D Winter 2011 Exam 2...

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