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Organic Chemistry II

by: Columbus Kerluke

Organic Chemistry II CHEM 2020

Columbus Kerluke
GPA 3.83

Yu-Lin Jiang

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Yu-Lin Jiang
Class Notes
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This 7 page Class Notes was uploaded by Columbus Kerluke on Sunday October 11, 2015. The Class Notes belongs to CHEM 2020 at East Tennessee State University taught by Yu-Lin Jiang in Fall. Since its upload, it has received 23 views. For similar materials see /class/221420/chem-2020-east-tennessee-state-university in Chemistry at East Tennessee State University.


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Date Created: 10/11/15
EXAM IV STudy Guide ChapTer 18 Recognize The eTher39 funcTionaliTy group Know how eThers are made UndersTand when To use a parTicular preparaTive meThod SynThesis of eTherconTaining compounds Recognize The sulfurconTaining funcTionaliTy groups ChapTer 20 Recognize carboxylic acid funcTionaliTy UndersTand why carboxylic acids are acidic Recall The ways To make carboxylic acids Recognized niTrile funcTionaliTy Recall The ways To make niTriles Review reacTions of niTriles O O O Hydrolysis ReducTion Grignard reacTions wiTh niTriles Review use of niTriles and carboxylic acids in synTheses ChapTer 21 Review carboxylic acid derivaTives O O O CarboxylaTe salTs Carboxylic acid halides acyl halides EsTers LacTones Anhydrides I SymmeTrical and mixed Amides primary secondary and TerTiary LacTams Review relaTive reacTiviTies of carboxylic acid derivaTives Recall how To converT one carboxylic acid derivaTive inTo anoTher Know how To separaTe a carboxylic acid from a mixTure of neuTral organic compounds ReacTions of carboxylic acid derivaTives 0 OOO NeuTralizaTion of carboxylic acids Hydrolysis saponificaTion for esTers ReducTion liThium aluminum hydride sodium borohydrideNOT hydroboraTionll Grignard reagenT addiTion To carboxlic acid derivaTives ChapTer 24 o Recognize primary secondary TerTiary amines open chain and heTerocyclic amines 0 Know why amines are alkaline in waTer o Recognize whaT affecTs The basiciTy of alkyl and aromaTic amineswhy some amines are sTronger Than oThers for example 0 Know how To make amines o NiTrile reducTion Amide reducTion Nucleophilic subsTiTuTion Gabriel synThesis ReducTive aminaTion o Hoffman and CurTius rearrangemenTs isocyanaTe inTermediaTe in boTh o Hoffman eliminaTionleasT subsTiTuTed alkene formed 0 Recognize The diazo funcTional group 0 Know how diazo compounds are formed 0 Sandmeyer reacTions of diazo compounds 0 Be able To recognize an azo compound 0 Recognize The funcTionaliTy of an azo compound dyes for example 0 Know how To make an azo dye o BasiciTy of heTerocyclic amines predicT The relaTive alkaliniTy of various heTerocyclic amines OOO Exam I STudy Guide ChapTer 14 Resonance sTabilizaTion of dienes ElecTrophilic addiTions To dienes 12 and 14 addiTion for dienes PredicTing major producTs for elecTrophilic addiTions To dienes consider relaTivie sTabiliTy of carbocaTion inTermediaTes and ZaiTsev producTs Use reacTion progress charTs To describe formaTion of Thermodynamic and kineTicallyfavored producTs Diels Alder reacTions whaT They are mechanism concerTed sTereochemisTry of The addiTionsTereospecific reacTion design experimenTs To invesTigaTe This UndersTand The difference beTween a diene and a dienophile ImporTance of S Trans versus S cis confirmaTion in open chain diene Endo versus exo addiTion Given a Diels Alder producT work backwards To idenTify The diene and dienophile ChapTer 15 Name basic aromaTic compounds menTioned in ecTures UndersTand why benzene is so sTable compared To an open chain Trienes for example UndersTand HLickel Rule and how To apply iT To deTermine if a compound is aromaTic or anTiaromaTic UndersTand The difference beTween aromaTic nonaromaTic and anTi aromaTic compounds Be able To recognize Them for example Learn To recognize if a heTerocycle or ion is aromaTic or noT ChapTer 16 Be able To wriTe The general mechanism for an elecTrophilic aromaTic subsTiTuTion reacTion Know The basic reacTions of aromaTic compounds halogenaTion sulfonaTion niTraTion Friedel CrafTs alkylaTion and acylaTiondon T forgeT The caTalysTs and possible rearrangemenTs for FC alkylaTionll UndersTand The limiTaTions of The Friedel CrafTs alkylaTion and acylaTion reacTions Be able To propose syn rheses for Targe r compounds using FC alkyla rion and acyla rion reac rionsdon r forge r The u rili ry of combining a Clemmensen reduc rion Wi l l l FC acyla rion Unders rand why a subs ri ruen r deac riva res or ac riva res The ring rela rive To benzene in elec rrophilic aroma ric subs ri ru rion reac rions Unders rand why ring deac riva rors are me radirec rors and why ring ac riva rors are op direc rorsremember halogens are excep rions Be able To use resonance con rribu rors To suppor r your discussions above Be able To use EAS reac rions To prepare diand Trisubs ri ru red benzene Targe r molecules STudy Guide for Exam II ChapTer 19 NaTure of carbonyl group why iT undergoes nucleophilic reacTions PreparaTion of aldehydes and keTones OxidaTion of alcohols To yield aldehydes and keTones eg PCC whaT do These iniTials sTand for TeTrahedral inTermediaTewhaT iT iswhaT iT does eTc ReacTions of aldehydes and keTones o Aldehydes are more reacTive Than keToneswhy HydraTion good idea To know mechanism 0 o Cyanohydrin formaTion and The uTiliTy of cyanohydrins o Grignard reagenT addiTion To carbonyls and limiTaTions of These reacTions o ReducTion wiTh LiAlH4 and NaBH4 ReacTions wiTh amines I Imines I Enamines I Oximes I Semicarbazides o AceTal and keTal formaTionuTiliTy of Thesebase sTable proTecTing group buT can be removed wiTh aqueous acid ChapTer 22 TauTomerism consequences of eg change of sTereochemisTry on The carbon adjacenT To The carbonyl carbon EnolaTe anion formaTion why are proTons on The carbon adjacenT To The carbonyl acidic AlkylaTion of enolaTe anions o KineTic versus Thermodynamic reacTion condiTions and how To use To make TargeT molecules ChapTer 23 Aldol condensaTionrecognize whaT an aldol is and how To dissecT a TargeT molecule To give The reacTanTs used To make The aldol Crossed aldol condensaTionhow many producTs How To force a crossed aldol condensaTion To give a major desired producT WhaT is an enone Learn To dissecT an enone To give The reacTans used To make The enone In rr39amolecular39 aldol r39eac rion and limi ra rions Ther e of Claisen condensa rionbe able ro dis ringuish a Claisen condensa rion from an aldol condensa rion for example 0 Mixed or crossed Claisen r eac rionssimilar39 ro crossed aldol r eac rions Dieckman cycliza rion in rr amolecular Claisen condensa rion Conjuga re addi rion r eac rions Michael r39eac rion Learn To dis ringuish a Michael condensa rion pr oduc r Robinson Annula rion r eac rionMADMichaelaldoldehydr a rion sequence Know how To recognize a Robinson annula rion pr oduc r r ing enone 1 5 dicar bonxlsl STudy Guide Exam III ChapTer 13 0 NMR basic Theory 0 EffecT of a magneTic field on nuclei focus on 13C and 1H 0 EffecT of field sTrengTh on energy sTaTes 0 Chemical shifTs shielding and deshielding 0 Be able To recognize The difference beTween 13C and 1H specTra 0 Be able To idenTify equivalenT carbons and proTons 0 Given a chemical sTrucTure be able To predicT how many signals There should be in The 13C and 1H specTra 0 Be able To apply The n 1 rule To decide upon The mulTipliciTy of carbons and proTons in 13C and 1H specTra 0 Index of hydrogen deficiency 0 Know where The infrared absorpTions occur for alcohols amines and carbonyl conTaining compounds 0 UndersTand how To deduce ThaT an oxygenconTaining compound mighT be an eTher aceTal or keTal absence of carbonyl and alcohol absorpTions 0 Given nmr and specTral daTa deduce The sTrucTure of a chemical compound 0 TMS and why iT is used as a sTandard in 13C and 1H specTra o SuiTable nmr solvenTs ChapTer 17 0 EffecTs of hydrogen bonding on physical properTies of alcohols o Acidbase properTies of alcoholssimilar To waTer 0 Know The ways To make alcohols 0 Know The reacTions of alcohols ThaT we discussed 0 Know reagenTs To inTerconverT alcohols wiTh alkenes alkl halides carbonylconTaining compounds 0 SynThesis problems uTilizing alcohols as reagenTs and producTs o AromaTic reacTions halogenaTion niTraTion Friedel CrafTs reacTions and Their characTerisTics o Grignard reagenTs addiTion To aldehydes keTones formaldehyde esTers 0 EffecTs of compounds conTaining acTive hydrogen on Grignard reagenTsalcohols amines waTer eTc


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