050422 - NAME: (please PRINT) Chemistry 1 093 Exam I April...

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Unformatted text preview: NAME: (please PRINT) Chemistry 1 093 Exam I April 22, 2005 Q Value Total Score 4x12 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. 3sz OH (A) ——_—-—“‘> 2. HO /H20 H Me // 1. n-BuLi, THF // (B) t ———-—-—> . | H 2. Mel I H OH OH 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° (a) ——————> 2. Jones reagent 1. H , Pd / BaSO (b) H / ___2_____4_, 2. CHZIZ, Zn(Cu) Sq 1. HBr, hv m 2. t-BULl, THF < how many diastereomers? 1. HBr, CH2C|2 ——-————————————-—-—> / 2. K+'O-t-Bu, THF \ ——————_—_.> \ 3. 0.5 Cu! 4. n-BuBr (d) 3. Exposure of dibromide 1 to the sequence of reactions below ultimately gives product 4. Br m 1. 'x' NaNHg, THF W ———._______> Br 2. n-Pr-I 1 2 excess Na°/Iq NH3 MCPBA <——-————————- CHZCIZ 4 3 (a) To convert 1 into 2, what is 'x' in step 1 above (i.e., how many equivalents are needed)? (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. ...
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This note was uploaded on 02/01/2011 for the course CHEM 109B taught by Professor Aue during the Winter '08 term at UCSB.

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050422 - NAME: (please PRINT) Chemistry 1 093 Exam I April...

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