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040128 - NAME(please PRINT Chemistry 1 093 Exam I Q Value...

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Unformatted text preview: NAME: (please PRINT) Chemistry 1 093 Exam I January 28, 2004 Q Value Total Score 1x10 3+6+8+9+4 1. Provide the major organic product(s) from the following transformations. Be sure to include stereochemical information where appropriate. 1. Lindlar reduction ————————-——> (3) ¢ 2. dichlorocarbene 1. K+ 'O-t-Bu Br -———-—-————-> 2. MCPBA )0“ Br NaNH2 (C) H THF, A 1. Na / liquid NH3 \ ——————-——> (d) N 2. Brz 1. HBr —-————-——-——————> (e) 2. Mg 3. D20 11. When alkyne 1 is treated under the following reaction conditions, essentially no reaction occurs (i.e., starting material is recovered). Why? Provide a brief explanation, and a solution (without changing the starting material) such that the reaction will take place and go to completion. Et W 1. n-BuLi, EtOH, 0°) é W 2.3-1 1 3. Draw a 3-D picture for the most stable vinyl anion intermediate in the reduction of 2-butyne with sodium in liquid ammonia. 4. Hydroboration of the alkene 2 below can be effected to give an intermediate X which reacts further to give isomerically pure product Y, an alcohol. ——-———--> ———> ———-—> 2 X Y Z (a) Provide the name for the starting olefin 2. (b) Give the reagent(s) to be used for effecting these transformations (2 to X, and X to Y). pmm Rwfl (c) Provide structures for X and Y (in the boxes). (d) Suggest a mechanism for converting 2 to product Y via X. (e) If Y is exposed to PCC, suggest the structure for product Z (in the box). ...
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