ReviewSet1 - -s into a resonance form it has a lower p K a...

Info iconThis preview shows pages 1–5. Sign up to view the full content.

View Full Document Right Arrow Icon
Chem 30C Winter 2008 Review Set #01 Chapters 19/23 By Tioga Martin
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
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 a. if an amine can donate its e
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
Background image of page 5
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: -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, , 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 Addn 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 O O 2 MVK Decarboxilate 1. [ NaOH (aq) ] 2. [ HCl (aq) ] 3. [ heat ] NaOH 1,4 Add'n 1,2 Add'n MeMgBr or MeLi NaOH NaOH Me 2 CuLi O O O O O O O O O O O O HO...
View Full Document

Page1 / 5

ReviewSet1 - -s into a resonance form it has a lower p K a...

This preview shows document pages 1 - 5. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online