07FH3ans - 1-((1R)-1-methylpropoxy)-3-hexanone OH B is more...

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b. Which is more stable, C or D? Why? 1. (12 points) Write out IUPAC names for each of the following: a. 2. (12 points) a. Which is more stable, A or B? Why? b. 3. (6 points) Reduction of E with Bu 3 SnH gives F . Deduce the structure of F , and draw an arrow- pushing mechanism for the transformation of E to F . Fall 2007 Homework #3 due: 10 a.m. Monday, September 17th c. d. Name ___________________ Chem 331 E O H O OH O O O OH Cl AIBN A B C D Bu 3 SnH F OH OH Cl Br C 8 H 14 13 C NMR 135, d 129, d 46, d 32, t (2) 35, t (2) 19, q (3S)-3,4-dimethyl-1-pentanol (1S, 2R)-2-methylcyclopentanecarbaldehyde 2-ethyl-2-propenyl (2S)-2-hydroxypropanoate
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Unformatted text preview: 1-((1R)-1-methylpropoxy)-3-hexanone OH B is more stable. In more stable chairs, methyl group is equatorial, so in A, OH is axial, in B, OH is equatorial = more stable. A B OH D is more stable. In the more stable chairs, the Cl is equatorial, so no difference. In the less stable chairs, the Cl is axial. In C, it would be 1,3-diaxial to one of the methyl groups. In the less stable chair of D, the Cl would only be 1, 3 diaxial to H's. D C Cl Cl R H-SnBu 3 Bu 3 Sn H-SnBu 3 + F Bu 3 Sn...
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This note was uploaded on 07/08/2008 for the course CHEM 331 taught by Professor Kramer during the Spring '08 term at University of Delaware.

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