Chem 634 Exam 1 Fa11 2006 Your Name 1. Show the products of the following transformations. Mechanistic details are not required, but be sure to indicate relative stereochemistry where necessary (four parts; I points each) Y a k 1 ) LDA, -78 "C b 2) Mel MeMgBr then H30+ H CI b rcChem 634 Exam 1 Fa11 2006 Your Name h/ 1. (continued)Chem 634 Exam 1 Fa11 2006 Your Name Y 2. The reactions below would not proceed as indicated. 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 ($ points each). A YChem 634 Exam 1 Fa11 2006 Your Name 2. (continued). d + E* 1) NaOEt EtO 2) H30+, A 1 equiv 1 equiv E*wChem 634 Exam 1 Fa11 2006 Your Name Y 3. Propose a reasonable mechanism. 1 p+5Chem 634 Exam 1 Your Name Fa11 2006 1 0 4a. Propose a mechanism for formation of B (m points) 0 1) A 0 Pr + CI2MeSiH cat Rh(l) 0 , A 2) H30+ HO? b p r 6 C 4b. Propose a structure for intermediate A. Be sure to indicate the double bond geometry (E or Z) and provide a rationale for the stereochemical assignment (Y points) 9Chem 634 Exam 1 Fa11 2006 Your Name 6. Propose a multistep synthesis starting with any materials that contain 6 carbons or less. Reagents that contain more than 6 carbons but do not get incorporated into the product (e.g. PPh3) may also be used. 2" F>
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