14D_f10_e02_key

14D_f10_e02_key - Chemistry 14D Fall 2010 Exam 2 Solutions...

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Chemistry 14D Fall 2010 Exam 2 Solutions Revised 11/17/10 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 projected course grade cutoffs, consult the grading scale on the Chemistry 14D course web page. 1. (a) 1. BH 3 2. NaOH, HOOH CH 3 OH Syn, anti-Markovnikov addition of water via hydroboration-oxidation. (b) H 2 Pt Syn addition of H 2 via catalytic hydrogenation . (c) Br 2 Br Br Anti addition of Br 2 . (d) CH 3 1. O 3 2. (CH 3 ) 2 S O O H CH 3 Oxidative cleavage of an alkene via ozonolysis. (e) CH 3 CH 3 NO 2 aq. HNO 3 aq. H 2 SO 4 Aromatic nitration via EAS. CH 3 is an ortho/para director; the ortho product is major because there are two ortho positions and one para position. (f)
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14D_f10_e02_key - Chemistry 14D Fall 2010 Exam 2 Solutions...

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