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Unformatted text preview: Chemistry 14D Fall 2006 Midterm 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. 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. (b) When HX adds to an alkene, the hydrogen of HX becomes bonded to the alkene carbon that bears the greatest number of hydrogen atoms. 2. Carbocation stability 3. (a) OCH 3 HCl and (d) HC CCH 3 HBr 4. OCH 3 H Cl OCH 3 Cl OCH 3 Cl rds 5. This is the rate-determining step because the carbocation is formed in this step. 6. Many answers are possible, as long as the alkene is more nucleophilic and the intermediate carbocation is more stable. In the case shown below, adding a methyl group converts the intermediate carbocation from primarystable....
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