ES_Chem233_MT_UBC - Chm233 Study Sheet PART I – BASIC...

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Unformatted text preview: Chm233 Study Sheet PART I – BASIC ORGANIC CHEMISTRY STRUCTURE, BONDING AND PROPERTIES C Markovnikov addition happens via the most stable carbocation. C R know orbital shapes electron configurations, valencies, Lewis structures C ESPECIALLY MECHANISMS C R/S designation Difference between enantiomers and diastereomers Meso compounds H RESONANCE AND AROMATICITY CH3 Huckel’s rules Resonance structure drawing H OH O OH H radical halogenation hydrogenation Br2, hν H H R 1 R4 R H H H OH R 2 Br diastereomers 3 Br HBr 1 R R4 R OH 1 R R 4 Br2 1 R 3 H R4 R R 2 R 2 H 3 bromination Base 2 R R3 dehydrohalogenation FUNCTIONAL GROUPS Br H2/Pd halohydarion O OH R H synthesis and reactions C H2 BrH2C HO H R ALKYNES enantiomers O R H Br R CH3 CH3 C H2 BrH2C R H R H H R HBr C ISOMERISM AND STEREOCHEMISTRY H3C R C meso compound hydration need to be able to recognize all of these nomenclature of all organic compounds base (R2, R4 = H) H3O+ OH H dehydration CHEMICAL REACTIONS AND EQUILIBRIUM 1 equilibrium equations and activation energy know how to draw reaction coordinate diagrams ACIDS AND BASES know certain pKa values understand how the apply to equilibrium reactions know the difference between Bronsted/Lewis acid Brønsted-Lowry Acids and Bases – A Classic Definition An acid is a proton donor. A base is a proton acceptor. Lewis Acids and Bases An acid is an electron-pair acceptor. A base is an electron-pair donor. Any electron deficient centre will be able to act as a Lewis acid (eg carbocations). The dissociation constant Ka for any weak acid in water is: Large Ka = strong acid (highly dissociated) pKa = -ive log Ka small pKa = strong acid Strong acid = weak conjugate base Strong base = weak conjugate acid and vice versa PART II – REACTIONS OF ALKANES, ALKENSE AND ALKYNES double dehydrohalogenation Base 1 R R4 R R 3 R 2 R 3 PART III – CARBONYL CHEMISTRY CARBONYL CHEMISTRY preparation addition reaction CARBOXYLIC ACIDS Properties and preparation of carboxylic acids Reactions of carboxylic acids LiAlH4 R OH alcohols O CrO3 H+/heat O CrO3 C N R O R'OH H+ R R H aldyhydes R O anhydrides carboxylic acids R'NH2 H+ H2O + H2O R' N H amides + H2O O esters O R R nitriles + R' OH R H+/ H2O O O SOCl2 ALKANES synthesis and reactions ALKENES synthesis and reactions O O Nucleophilic acyl substitutions Nu R Cl R Nu acid chlorides We’ve helped over 50,000 students get better grades since 1999! Need help for exams? Check out our classroom prep sessions - customized to your exact course - at CARBOXYLIC ACIDS DERIVATIVES The aldol condensation between two aldehydes to give a β-hydoxy aldehyde Nucleophilic acyl substitutions Anhydride preparations and reactions LiAlH4 R OH alcohols O CrO3 H+/heat O CrO3 R R H aldyhydes O R' OH carboxylic acids H+/ H2O R R + O H R 1 H3C 3 3 2 5 4 O R aldol reactions can occur intramoleuclarly to give cyclic products (favouring 5 or 6 membered rings) 2 1 H 4 5 H O Nucleophilic acyl substitutions Nu aldol products can dehydrate under acidic or basic conditions to give the conjugated product H O O amides Cl H O R H2O N H SOCl2 O R H w H2O OH R' R H O R nitriles O mild base H2O + + O esters R'NH2 H+ OH O H R N C R O anhydrides R R'OH H+ OH O O HO Nu Claisen condensation is similar to the aldol reaction, with esters as the starting material acid chlorides CARBOHYDRATES – (IGNORE IF NOT COVERED) PROPERTIES OH REACTIONS AND OEt OAc OAc ester formation OCH3 Ac2O pyridine OCH3 OCH3 ether formation NaBH4 R OH OH reduction OH Br2/H2O O HO HO OH OH mild oxidation O HO HO OH MeOH H+ OH HO HO OH CH3I Ag2O O OCH3 OH glycoside formation O O HNO3 HO O HO HO OEt OH O H3CO H3CO R OH OAc OH HO strong oxidation HO O mild base Fisher, Haworth and chair conformations Reactions, including Kiliani-Fisher and Wohl AcO AcO O O O OH OH PART IV – RADICAL α TO THE CARBONYL ENOLATE CHEMISTRY Enol tautomerization and structure Reactions at the α position of carbonyls (β) Elimination of malonic esters CARBONYL CONDENSATION REACTIONS Aldol condensation (mixed, intramolecular, etc) Claisen condensation (mixed, cyclizations, etc Our Course Booklets - free at prep sessions - are the “Perfect Study Guides.” OEt ...
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This note was uploaded on 10/24/2011 for the course CHEMISTRY chem taught by Professor David during the Spring '11 term at UBC.

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