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Unit%204_32_2008 - h Isoprenyl pyrophosphate synthesis(page...

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C HEMISTRY 0320 - O RGANIC C HEMISTRY II Prof. C. S. Wilcox - University of Pittsburgh Unit 4 Reading: Chapter 18 + 14-10 + page 1066-67 I. Mechanisms. a. The aldol reaction. (Enolate addition to aldehydes and ketonesRobinson ring annulation. b. Acid and based catalyzed keto-enol equilibration. c. Acid catalyzed halogenation of ketones and aldehydes. d. Base catalyzed isomerization of α− substituted ketones. e. α -Halogenation of ketones. (Acid and base catalyzed.) f. Geranyl pyrophosphate synthesis (page 641). g. 3-Oxobutanoic acid thiol ester synthesis (page 887).
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Unformatted text preview: h. Isoprenyl pyrophosphate synthesis (page 1067). II. Reactions. a. You should be able to provide examples of reactions and reagents described in the following list. i. Robinson ring annulation. ii. CH 3 Li – 1,2-addition iii. (CH 3 ) 2 CuLi – 1,4-addition iv. Br 2 , H + – halogenation v. Michael addition vi. KCN, H + – 1,4-addition vii. Crossed aldol reaction viii. Enamine alkylation III. Synthesis. Homework problems 18-56 to 18-58 provide good practice in applying these reactions....
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