Chem 634 Professor Fox Exam 3 May 21 2004 3 hours Your Name Chem 634 Exam 3 May 21 2004 1 Your Name Provide reagents for the following transformations Mechanistic details are not required but be sure to indicate relative stereochemistry where necessary six parts 3 pts each More than one step may be required a H H H MeO H H O O b O O Chem 634 Exam 3 May 21 2004 1 Your Name continued H c O d O O Chem 634 Exam 3 May 21 2004 1 Your Name continued e OH O Ph H Ph O f Et Me S O Me Et R Chem 634 Exam 3 May 21 2004 Your Name 2 Predict if each of the following reactions would proceed as written If you feel that the reactionwould proceed simply write will proceed as written If you feel that the reaction would not proceed as written provide a brief but detailed explanation and indicate the structure of the product s that would be formed instead of or in addition to the product that is drawn 3 points each O a OMe b O Ph S O Ph Fe CO 5 OMe h 1 2 MsCl 3 Na Hg CHO Ph Chem 634 Exam 3 May 21 2004 2 Your Name continued O c d H2N NHTs NaBH3CN CO2Me Me CO2Me O NaOMe Me CO2Me Chem 634 Exam 3 May 21 2004 2 Your Name continued 1 mCPBA e Me Et SPh H f H 2 P OMe 3 MeOH H H O Et OH H LiAlH4 H H HO Me H Chem 634 Exam 3 May 21 2004 Your Name 3 Provide a detailed arrow pushing mechanism N 1 BuLi NHTs 2 H 15 pts Chem 634 Exam 3 May 21 2004 Your Name 4 Provide a detailed arrow pushing mechanism 2 equiv Ph Cp2Ti O O O O Cl AlMe2 Ph O O O 15 pts Chem 634 Exam 3 May 21 2004 Your Name 5 Consider the following reaction Et Et 1 LiHMDS N 2 H NH O LiHMDS TMS 2NLi O a b c Provide an arrow pushing mechanism 5 pts Propose a transition state model for the transformation 7 pts Based on your answer to b what does the relative stereochemistry of the product tell you about the stereochemistry of the enolization In otherwords do you form the E or Z enolate Explain your answer 7 pts Chem 634 Exam 3 May 21 2004 Your Name 5 Propose a synthesis using any acyclic materials MeO2C N 15 pts H3C CH3 O
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