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Fund of Organic Chemistry II

by: Dominic Kling

Fund of Organic Chemistry II CHEM 3332

Marketplace > University of Houston > Chemistry > CHEM 3332 > Fund of Organic Chemistry II
Dominic Kling
GPA 3.71

Thomas Albright

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Thomas Albright
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This 27 page Class Notes was uploaded by Dominic Kling on Saturday September 19, 2015. The Class Notes belongs to CHEM 3332 at University of Houston taught by Thomas Albright in Fall. Since its upload, it has received 53 views. For similar materials see /class/208158/chem-3332-university-of-houston in Chemistry at University of Houston.


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Date Created: 09/19/15
1 Common names use alkyl name ether HSC CHg Dimethyl ether Q Hsc b CHECHS Fu ran Ethyl methyl ether CHBCHg b CH2CH3 l 5 Diethyl ether ether 0 Tetrahyclrofuran THF emacizoiicHg tert Butyl methyl ether iCHa CHSCH2 CHCH2 Ethyl vinyl ether Methyl phenyl ether anisole 2 IUPAC nomenclature name the most complicated part as the alkane and add the rest as an alkoxy substituent in alkyl name drop yl add oxy Remember the alkoxy name is only a higher priority than the halides It is even lower than the alkyl substiuent 4 3 2 1 CHs IDH CHz CHz OCHs Br 3Bromo1methoxy butane cis3t butoxy 1methylcyclopentane actually the SR enantiomer as drawn 3 Cyclic ethers a common names 0 H H CH2 CH2 H CH3 ethylene oxide propylene oxide Chapter 14 2 b IUPAC tWO ways 4 a Name as an epOXide Name as an 0X1rane H 2 I lPh CH3 EH 2CH3 Best 1 5 E2ethyl3methyl2phenyloxirane E23epoxy3phenypentane o o 1 5 A 0 Eihylene oxide Trimethylene oxide Furan oxirane oxacyclobutane oxetane 0 E0 0 o o Tetrahydrofuran Tetrahydropyran ioxan THF peniamethylene oxide 14 dioxacyclohexane oxacyclohexane 0A0 O O k J O 13Dioxolane 135Trioxane 3 mavdioxacyclopemane 13Svtrioxacyclohexane an acetal of formaldehyde paraldehyde B Uses 1 solvents have moderate polarity and are unreactive for the most part 0 CHscHz O CHZCHa lt 7 THF Et20 2 feedstock chemicals O o CHz CHZ A CH3 3 polymers Igt part of epoxy glue CH2 CH CHZCI Chapter 14 4 biological we ll see some more later H CH3 I OCH3 f C CHzCH2 H Juvenile hormone prevents maturation of insect larvae Chapter 14 5 forming complexes 21 6 electron reagents storage Mg R CI R Mg Cl o 5lt F B39 gt a b crown ethers etc 2 1 E 1 w KIOIQ 1270rown4 18 Crown6 p m N Q o o 39 390 0 C5 I o u I x ON 0 I Na A lt Na7773 xx I guest 0 O C i quotQ Li a K x KQ I N j I i ost inclusion compound 0 q 390 r O Cavity Ji Ia ecrown7722 A w I K 5 2 TH F CH3CH2CH2CH2 OTS KF CH3CH2CH2CH2 F 1 8 crown 6 A cryptand Chapter 1 4 7 1 IR naming w Biff if Gig g wiS I D Synthesis of ethers 1 Industrial bimolecular dehydration a overall reaction A a o a H2304 R s must be the same b mechanism CH3O4H CH3E cH3OH H CHs O CHs ms 56m H29 H H30 Chapter 14 2 Williamson Synthesis a overall reaction M 3N2 only ROH gt n039M Rx gt ROR39 MNaK X Cl Br I OTs etc OH gtKOH 0 pxylene 140 DC 7 h Br 33 H IC CH3 HaC CH H C CH k Na OCHgCH 3 3 OH gt39 3 c CH HOCHQCHS I Br H OCHECHS E2 3N2 75 25 CIHE HJC5fct39l 48 3N2 lmpossible on quot l quot ternary halide CH3 CH3 CH3 I s 2 l chiT g Hac Kjg Lgt H307C70CH3 9 CH3 CH3 The Williamson ether symhesls cannol 10 be used to make cliren bulyl ether CHaJaCOCCH33 3 Oxymercuration demercuration 21 overall reaction 1 HgOAc2H20 H OH gt 85 2 NaBH4 And so using ROH in place of H20 1 HgOAc2ROH H OR Markovnikov addition anti addition gt 2 NaBH4 Markovnikov addition anti addition b mechanlsm Issues HQOAC H 0A R 9 C HgOAc Hg0Ac F v R R cCH2 gt CiCHZ CiCHZ lt gt CicHz H20 H H H H ESHZ A mercurinium ion addition R HQOAE R HgOAc 1 deprotonaiion I H T CHz gt H T CHZ H30 0 OH HgtH6Hq 11 Ring opening by breaking the Initiai isolable weaker carbonrmercun bond c examples 1 HgOAc2CHSCHEOH W 25 CC 10 min 2 NaBmNaOH OCHaCHa 2 h quot 98 E Reactions of ethers not many 1 Cleavage by strong acids a overall ROR39 HX gt RX R39X b mechanism excess47HBr 0 8h O klrlv I ilr 1L HE could be SNl Chapter 14 In some cases 12 c examples 0 h 39 O 2 AutOXidation a overall reaction 90H R39O CH2R39 Ogt RoCHR39 R OO39CH2R39 2 hydroperoxide peroxide b partial mechanism H H H Stable 6 Hb I H free radical Chapter 14 13 0 5 H log Hydroperoxides 6 ask b39 gt abifo Peroxides NOW R39OO39CHZR39 gt RO39 R39CH2039 gt ETC heat given Off H BE VERY CAREFUL IN STORING ETHERS H Chapter 14 14 F Sulfides l Nomenclature a common drop ether add sulfide l g j ch S CHg H3C S CH2 CH3 gt SquotS lt Dimethyl sul de Ethyl methyl sul de tenButyl cyclopentyl sulfide Dicyclopropyl disulfide b IUPAC replace alkoxy name With alkylthio 2 Reactions a oxidation Chapter 14 15 The general case 0 H203 H202 R S R gt R S S R Sulfide Sulfoxide ll Sulfone Specific exam ples O 30 H202 gt 39 CH OH NaOH s s 39s O 90 gt CHSCOOH 6 S 50 0 20 76 Chapter 14 b preparation using thiols The general case HES H j HES RBEr its H ng H u Hfe H A s pem c examp e Jr GHSGHE CHECHQGEHECHE K KBE CHH CHECHECH2 CHECHS Mama C reactlons substltutlon SNZ 1H C CH CH CH3 S 2 3 2 3 3 s 2 HBC E CH3 III mgrECTElt 7 wig CHE f EHq CH3 CH3 WEEK h A su mmum 10M NH3 301 NH2 N N 3 2 Rg Ec Us lt O gt HQCHS CH2 0 N N H H Ch HO OH Sj Adie nosyilmethinnine G EpOXides 1 Preparation 21 Reaction of Olefins With peracids gtlt WA 812 RCOsH o RCH3 ops Cl MCPBA H CHNCOOOH o 20 Dc 3 h C C n C C one step H quotquotH CH3CH27 CH27COOH syn addition CH3CHQ7 CH27COOH Oleic acid 82 Chapter 14 18 b Reaction with halohyd ns X2 H20 x Cl Br I mom R Base 39OH etc H NaOHHEO 25 1 h quotaquot 3 N2 Chapter 14 S An OXIrane 73 X base gt Ai F gt W I o OH 9 39 39 3N2 9 91 epoxide H26 2 Reactions of epOXides 0 ring strain Free energy ethylene oxide 25 kcalmol 105 kJmol diethyl ether Progress of the reactionr a Acid catalyzed ring opening general H o H Ho0 O N 8N2 normally 20 Chapter 1 4 The mechanism of epoxide opening in acid H5 H 6Ha H f lJr S d H0 rotonation 0 2 e rotonation 9 ij i P H35 H20 q H H gH H20 H20 This weaker carbon oxygen bond wil be the major bond broken by an adding nucleophile The general case Hac A specific example 7i THE f f CI H36 C CH2 Hn ch f CHZ HscC CH2 H30 9 H30 0 55 45 21 Chapter 14 b Ring opening under basic conditions H o39H C L 0 bH 02 S 2 i 139 C N pro aria Ion H9 0 H9 H0 Alkoxide 6 quot57 0 0 gt 1 gt lr Ho39 H9 HQ Transition state the ring is partly opened The general case 20 6 5H H C i HNLJ I 3 c CH2 4 HSC C CHQ a HSC l Cl 12 Nu HsC N H30 NU H30 N A speci c example 0 6 6 Na N H202 n HaCc CHZ quot sc C CHZ Hac C CHQ H9 HZOdinxane l i H30 80 C H30 N3 H30 N3 41 0 7b H Na quotQCHS chr I3 C CHE gt H IC CHZ gt H HOCH CH3 quot 3 CH3 IQCHa Ph Q 5 HC CH 1PhMgBr I C 2 H26 gt gt 2 350020h H I 3 CH3 CH3 Ph Ph V 1LiAIH4 O ether 25 C 3 h H 2 H20 Igt Intermediate alkoxides EID39H f C12 bCH3 CH3 QCHB 5H H C CH2 CH3 Ph 60 Eh OVOH H An aside into the land of barbequeH Y OH I Y Q 4 Bad reactlon O arene oxides 6 addition product OH E i 4 OK reaction rearranged product Chapter 14 24 gt 9 gt I P7450mono pOXIde oxygenase hydratase Haw Benzapyrene O OH quot C NI W N SUgar Guanine P450m0n0 oxygenase 9H 20 c n N W a u u N N Suar S 9 H0 ugar HQ QH A segment of DNA H Summary 1 Ethers a nomenclature amp spectroscopy b preparation i Williamson synthesis ii alkoxymercuration demecuration c reactions i acid catalysed cleavage ii auto oxidation 2 Sulfides a nomenclature b oxidation reactions to sulfones sulfoxides c preparation analog to Williamson synthesis d sulfides as nucleophiles Chapter 14 26 3 Epoxides synthesis a reaction of olefins With peracids b cyclization of halohydrins 4 Epoxides reactions a acid catalyzed ring opening b nucleophilic ring opening under basic conditions Chapter 14 27


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