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050422-key-detailed

050422-key-detailed - NAME Defined Awswaf Kég(please...

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Unformatted text preview: NAME Defined Awswaf Kég/ (please PRINT) Chemistry 1 093 Exam I April 22, 2005 0 Value Total Score 2x10 4x12 48 3+10+4+15 32 100 “We’re scavengers, we’re ugly, and we smell bad. If we didn’t laugh, we’d crack." 1. In each of the following reactions there is an error in the chemistry as shown (e.g., with the predicted product, the reagents, or both). Why? Provide a brief explanation (without changing the starting material). 1- Bsz OH 2. HO /H20 H // 1. n-BuLi, THF . ‘H 2. Mel OH (A) 2. Provide the major organic product(s) from the following transformations (in the boxes provided).. Be sure to include stereochemical information where appropriate. 1. 03,-78° 37’“ (a) 2. Jones reagent L? /f(\0%-2 "20 m 0” 0 0H 1. H2, Pd/BaSO4, 41/111 2. CHziz, Zn(CU) CH1”, " “Q < how many diastereomers?_____ 1. HBr, CH2C|2 (C) 7&1; K+O- t-Bu, THF "SW 1. HBr,h 2. t—BuLi, VTHF (d) M ‘ H 3. 0.5 Cul i 4. n-BuBr Br ar—HI . 1%“ rat/V H /\=/'”—::--> 3. Exposure of dibromide 1 to the sequence of reactions below ultimately gives product 4. Pr Br W 1. le NaNHz, THF W Br 2. n-Pr-l 1 /\,Cj 2 1-.- LW 6 :LNZIIJHL // Him“ // ___.._9 /j/\/“—“" lexcess Na°/|q NH3 8r MCPBA CHZCIZ 4 (a) To convert 1 into 2, what is 'x' in step 1 above (i.e., how many equivalents are needed)? 3 (b) Provide structures for products 3 and 4 (in the boxes). (c) Provide the IUPAC name for compound 3. (d) Suggest a mechanism for converting 1 to product 2. WW ...
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