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Unformatted text preview: a. if an amine can donate its e-‘s into a resonance form it has a lower p K a e.g. 4. Sterics a. less freedom of motion from constituents the greater the p K a e.g. Mechanism and Retrosynthetic Analysis 1. Number the carbons 2. Identify key features (functional groups, α , β unsaturations) 3. If you know a reaction that can be done forward (decarboxilation, reduction) than you can add functionality to barren positions of a molecule in retrosynthesis. 4. Look for key intermediates of known reactions e.g. 5. 1,2 v. 1,4 Add’n O R R 1 2 3 4 Hard Nucleophiles go 1,2 MeMgBr MeLi Soft Nucleophiles go 1,4 H 3 COOC H 3 COOC Me 2 CuLi Na Practice Problem for Ch. 19 O O base? 2 A A base? MVK B Decarboxilate 1. [ ? ] 2. [ ? ] 3. [ ? ] C D NaOH D D 1,4 Me Add'n 1,2 Me Add'n ? ? E F...
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This note was uploaded on 08/21/2010 for the course CHEM 30C taught by Professor Kwon during the Winter '08 term at UCLA.
- Winter '08