Chem316F03MT4a - Chem 316 F03 Page 1 of 7 Kantorowski Exam...

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Chem 316 F03 Page 1 of 7 Kantorowski Exam IV 20 November 2003 Name: ___________________________________________ This exam contains 4 pages of questions – confirm this once you begin . You will have 80 minutes. No models or calculators are permitted. Read all questions carefully – answer the question that is asked! Illegible or indecipherable answers may not receive potential partial credit. Good luck! 1. (6 pts) Identify each of the following as nucleophilic (N), electrophilic (E) or neither (0). If a nucleophile also indicate if it is an ambident nucleophile (A). LiOCH 3 NaNO 2 Cl OTs N E E E N, A 0 Both N and O have an available lone pair The ultimate C electrophile... a carbocation!
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Chem 316 F03 Page 2 Initials________ 2. (4 pts) For each of the following rate equations indicate the effect of doubling the concentration of component A. a) rate = k[A][B] rate doubles b) rate = k[B] no effect (A is not involved in the RDS) c) rate = k[A] rate doubles d) rate = k[A] 2 rate quadruples 3. (9 pts) When ( 2R , 3S )-2-bromo-3-methylpentane is treated with ethoxide there are three elimination products possible (compounds A , B , and C ). H Br CH 3 H O OH Na A B C H CH 3 + + a) Provide a complete and detailed mechanism (i.e., electron arrow pushing) that accounts for the formation of C . H Br CH 3 H Na C H CH 3 H O Identify a proton b to the C bearing the Br. Na O H Br + + b) It is found that only one of the internal alkenes is formed. Determine whether A or B is formed and clearly justify your choice. H Br CH 3 H The mechanism is E2; see question #7 Look down C2-C3 bond. The b -proton to be deprotonated is on C3 CH 2 CH 3 H CH 3 CH 3 H Br 2 3 Need to be anti periplanar CH 3 CH 2 CH 3 H CH 3 H Br H 3 C CH 2 CH 3 H CH 3 H Br H These groups will be cis once the p -bond forms B
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Chem 316 F03 Page 3 Initials________ 4.
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