review1 - a. if an amine can donate its e-‘s into a...

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Order of Precedence for Functional Group Nomenclature Ether < Amine < Thiol < Alcohol < Ketone < Aldehyde Prefex R–oxy amino– mercapto– hydroxy– oxo– oxo– Suffex ether amine –thiol –ol –one –al < Nitrile < Ester < Amide < Carboxilic Acid Prefex cyano– R–oxy R' amido– carboxy– Suffex –nitrile R–yl R'–ate –amide –oic acid 1. Identify stereochemistry 2. Identify functional groups and their priorities – func. Grp1 is lower priority than func. Grp2 3. Identify longest alkyl chain (#R, #S) – #–func. Grp1 Alkyl chain #–func. Grp2 Trends in Basicity of Amines 1. Inductive Effect a. e - donating groups (e.g. alkyl) increase p K a b. e - withdrawing groups (e.g. halogen) decrease p K a 2. Geometry a. greater S character lowers p K a by being more e - withdrawing sp3 > sp2 > sp by the relative p K a ’s 3. Resonance Stabilization
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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.

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review1 - a. if an amine can donate its e-‘s into a...

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