1. Chemistry 125: Lecture 69 April 16, 2010 Decarboxylation (Ch. 17) and Acyl Compounds (Ch. 18) This For copyright notice see final page of this file

2. Decarboxylation (sec. 17.7g) malonic acid  acid (concerted) OH 2 HO OH C O H O -CO 2 enol

3. Decarboxylation (sec. 17.7g) also  -keto acids  ketone OH 2 HO R C O H O -CO 2 enol

4. Decarboxylation (sec. 17.7g) or CO 2 as leaving group from XCO 2 - or RCO 2 (pp. 859-861) RCO 2 Ag Br 2 RBr + AgBr + CO 2 “Hunsdiecker Reaction” RCO 2 H Ag 2 O ? 1833-1887 Tony award 1954 Alexander Porfiryevich Borodin

5. Spectroscopy pp. 888-889

6. acyclic anhydride in phaseout of phase

7. cyclic imide in phase

8. A/D Substitution via Tetrahedral Intermediate pp. 890 (Fig. 18.22) 886 (Fig 18.17)

9. Going All the Way to C-OH pp. 891, 898-9, 903 (C-NH 2 )

10. Stopping Part Way to Preserve C=O pp. 892-893 (Fig. 18.22) 900 (Fig 18.38)

11. Acidic / Basic Hydrolysis of RCN pp. 904-905 C-OH O

12. Acidic Hydrolysis of RCN

13. Basic Hydrolysis of RCN

14. End of Lecture 69 April 16, 2010 Copyright © J. M. McBride 2010. Some rights reserved. Except for cited third-party materials, and those used by visiting speakers, all content is licensed under a Creative Commons License (Attribution-NonCommercial-ShareAlike 3.0).Creative Commons License (Attribution-NonCommercial-ShareAlike 3.0) Use of this content constitutes your acceptance of the noted license and the terms and conditions of use. Materials from Wikimedia Commons are denoted by the symbol. Third party materials may be subject to additional intellectual property notices, information, or restrictions. The following attribution may be used when reusing material that is not identified as third-party content: J. M. McBride, Chem 125. License: Creative Commons BY-NC-SA 3.0