Vogel's TEXTBOOK OF PRACTICAL ORGANIC CHEMISTRY 5th ED Revised PDF
Preview Vogel's TEXTBOOK OF PRACTICAL ORGANIC CHEMISTRY 5th ED Revised
TEXTBOOK OF PRACTICAL ORGANIC CHEMISTRY FIFTH EDITION B.S.FURNISS + A.J.HANNAFDRD * P.W.G.SIMITH * A.R.TATCHELL VOGEL’s TEXTBOOK OF PRACTICAL ORGANIC CHEMISTRY ITH EDITION [Revised by focmer und curren! members of The Setoo! of Chemisty, eames Pelylechme, | ond Brian §. Furniss Antony J. Thannaford Pour W. smith Austin R, ‘Yatchell Ploneme Groep tins 169 inc perm fra ne ee aga ikea of Comes Calan Pabst Dace Trot tn ape waren Wh seen i ie sae lw 8 Ba Sass Fe Se peaine cee aca Te CONTENTS CHAPTER 1 GRGAWI SYNTHESIS 4.1 mtRORUCTION 412. STRUCTURE OF THE TAREET MOLECULE 1.3 ACTION MECHA AND THE ETHADOLOGY OF SHNTHESIS 1 EAETION MEZHARIGM AND THE ATHATEGY OF SYNTHESIS 1.5, CORDLUSION FEFCRENCES CHAPTER 2 EXPERIMENTAL TECHNIQUES: 24, GENERAL WSTBUCTIONS FOR SAFE WOERING PW RBRWC CHEMICAL ahonarones 22 PLANNING OF EXPEEINENTS AN RECORDING OF HESIKIS 23. HAZARDS IW ORGANIC UHEUSTRY LABORATORIES 21 Intodetin 332 Explosion and fre harands 38 233 Reactive morgane feagents 2 2134 Hanae duet tonle chemicals 44 233 Elect eatery 31 236 Lltravioet radiation $2 APPARATUS AND REACTION PROCEDURES 24 INTERCAAGEABLE ENONND LASE J0UKTS 25 TYPES OF GROWAD GLASS AOUHTE 26 CARE AND KAINTENAWCE OF EROUKD GLASS JOUNTS ‘27. APPAMATUS WITH INTERCHPMEANLE GROUAR GLASS JOINTS SUITABLE FOE GEMERAL USE 1M PHEFARATIVE OBGAAIC CHEMISTRY 25 THER TYPES OF ANTEECHAMGEABLE JOINTS ANU STORCUCKE ‘Zp THE USE OF CORKS AND HUBBER STOPPERS ‘21H CATTME AND BERDING OF LASS TUBING 0 Oa 241 GENERAL LASORATOEY APPAEATUS 242 COOLUNE OF REACTION ROCTORES 2.12 HEATING OF REACTION WAKTORES 216 MECHANICAL ACTA 245 TYPICAL GROWRD GLASS JOUNT ASSEMBLIES FOR STANDARD REACTION PROCEDURES 245- PRECAUTIONS FON URATTENDED HEACTIONE 217 arvana fon seo neacronTcamaUES ‘neotalye and catalysed tayour phase reactions 99 Oronotysis (08 TIDE Organte photichemisry 106 ING Electrolyte (andl) syntheses. (15 E07 Liguit ammonia tecaiques LG TS Reactions lmabing aicserste compounds. 120 ISOLATION AND PURIFICATION PROCESSES IE. GENERAL CONSIDERATIONS 2214 FALTERMON TECHRIDUES 20 RECRYETALUSATION TECHMOUES 221 SUBLIMATION TECHMIGUES FREEZE ARYINE 222 SOLVENT EATRACTION 2223 DIVING OF LIUIBG OR OF SOLUTIONS OF ORGANIC CUMPOUADS IN oveauic SOLVENTS 224 DISTWLLATION AT ATROSPAERUC PRESSURE 225 STEAM UISTILLATION 222K FRACTIONAL DISTILLATION AT ATIADSPHEEIE PRESSURE ‘227 NSTLLATOW UNDE OIBAMISHED PRESSURE {YACLN’OBsTHLATION) 122% HCH VACUUM BISTILLATION — MOLECULAR DSTILLATION 223 VACUUM PONDS 230 ANOWETENS, VACUSTATS, ACU GAUGES AND MANOSTATS. 231. CHNOBATOSRAPHT 1232. STORAGE OF RARPLES DETERMINATION OF PHYSICAL CONSTANTS 2:3 RELTING POINT — MUCED MELTING POTS 234 DETERMINATION OF BOWLING POINT 2.3% DETERMINATION OF MOLECHLAR WEGRT 23% DETERMINATION OF OPTICAL ROTATOR PORER ‘237 BETERMMATION OF REFRACTIVE (VER EFERENCES eas oyag CHAPTER 3. SPECTROSCOPIC METHODS AND THE INTERPRETATION OF SPECTRA ms Inrotction 254 The efeceomugueti ypectrum 285 ‘2t wmanen soecTenscoPy Bi Tstramentalfetares of infered spoctrophotometers 258 Determination of trad spectra 250 Sample prapareion 260 Feature ofan Iafared spectrum 258 Interpretation of am ifiared spectra 271 Characteriie group frequenctes 213 232 NUCLEAR MAGHETIC HESONANCE sPécTRaSEOPY sme Fearne ofthe macear magic resmance spectrum 8 he eheareal ifr 34 Splespin splicing 338 ‘Prato attaches heterstoms SR ‘Simplifearon of spectra 360 “erpretation of he pn. specerume 399 ter information from Capecoa 0 ‘83. mass SPECTEORERY m The muss cram 362 Anpcaronce ofthe mass pect 372 Titerctation of thr mans Spectrom 3T3 ast spectra of lasses af organi compounds 313 ‘M4 UTRRMOLET VisMLE sPECTRDSZOFY as Increnta fecaeee of elnarelet siitespectropheometers 384 Determination of wlio ite spectra 384 Saver of he absorption S88 Schnts for alravotlspecroscuny 386 Sotto preparation 386 (Optica cele and toh crs 387 Feauurs of an wlravolt-tbespeciam 388, FEFERENCES an CHAPTER 4 SOLVENTS AND REAGENTS 15 \AL_ THE PURIFICATION BE COMMON CRGARIC SOLVENTS 5 Saturated allphatte hyeocathons 397 Atomare hydrocarhane 39% Nitrogee containing solvents 409 Suiphur-conaining solvents 411 Phosphorescomtating solcats 412 (42. THE PREPARATION AHO PUIFCATION OF REAGENTS cy REFERENCES - CHAPTER 5 ALIPHATIC COMPOUNDS ™ 51 ALKANES ™ ‘Sieve 40 ‘Snmry of prepartine methods and ofretvoynthotesratles $11 ‘Spectroseopis features “472 Sun Thr eatalyleRydrogsnasion and chencal reduction of alkenes 72 5.12. The hydrolysis of allvinagacsiam bales and the Aydrogenoljsisof ale hales and oF aly mac elven poulphunates 74 5:3 Tne roduction af aifenpdes and betones 476 S14 Comping renetons (a sing ongamometalc compounds, und 7 52 AIMEE ue ‘Serctere 484 ‘Summary af preparetve methods and of ceroxpnheticsrateies 88 ‘Spoetascops footres 85 ‘52. 2 Flimbnartos processes (Blnination) 456 522 ‘the paral hydrogenation of alkynes 4193 S23 Wits and reed reaction: 395. B21. Gulceted wenreangements of nlbyees tv allonce S04 a ALKYmes wr Siciare $07 ‘Sermmary of preparative methods and of retropubic strateies SOB Of nes and gemalthabdes 519 ‘The oxidation of hydrazones of ketones $12 Aliglaon of terminal alkyne 13 3.3 Coupling reaclons coding to dynes S15 EO ALPANTIC ALCONDIS a7 Spemtare 512 ‘Semmary of prepartine methods unl af retvacsmthetic wraegies S17 Spectrocoplefatores $19 EAU The redacton af allen, Ketones aol esters S19 42 The lneractina of carbony-conianing omponis with seganonaetalc esgents 1 5.43 The bedroborationoxldatn of alkenes 502 Sd Tee oxgmercuraton-demercuratin of alkenes S48 SAS The hsdrosglation of alkenss 547 SAS. Methods tor the protection af the hydroxy! gap 550 55 ALPHATIC HALIDES = Srmctire 553 ‘Semonary af proparotive mothods and of tetrosputhete swathes S84 Srectrwconi fetes 34 3 Prepacition of alll chlorides fom alcohols 588 Prepivaton of alkyl bromides fom akohols S59 Preparation of wks] foes fom nbebels S68 [Displaceren! resins mols legen atom S70 P1 resctlonsInvlviy a ethanephensloey 56 Dinplacsmcutscactonstvolsiy the anne stony 4 5.87 Adiiton of drogen hallo or halogens to alles. 74 5.88 The eepacenent of reardveallyle Hydrogen ats by bromine 577 6 AUUTIC ETaERS va Sirnsnie 79 ‘Susnney of preporeive methods and of vetrospmhete sraugles 580 ‘Specroscpis features $89 [SET The formation of ether from alcohols under aciic ian ofa aleshal with halogen compound under base canals. 83 ‘AD AMIPRATIC ALDEITRES sts ‘Siructie 588 ‘Suowny of preparative methods and of tetrosymhetleseateies SBE Sercraropt feaanes 9 ‘The contra oxidation or dehydrogenation af primary sleohole 587 5:12 The oxldathe deavage of 1.2-dols 590 [ET The exanolyss of sallably substtate alkenes $82 EVA The reduction of wells, eadboxylic ulde and carboxy seid chlorides 54 53.8. Methods based upon alkyl halides £96 528 The hydatyis and decarboxylation of epoxy eters elvsilic eter) 598 5.77 The onidatve hydrolysis of wonate salts derived from primary eitroathunes 599 5.78 Maths tr the skslaion uf che carbon chin 600 ‘EE AUPHKTIC KETONES om Srrurrere 4 ‘Sinory of preparative methods andl ofretrozythaicwraegier 0S Specrocenie features 006 S81 The oxidation of swcondary alohols 607 SB2 The hydration of ayes 612 SBS The thereal decbosyhlian of wcde oor & ctl oxi cara 2 ‘Ra The imeracrign af organometsiecompounss with carbone acd cadide and NN iaetisiearlveymites 616 585 The hydrolyse and decaelnylation of frhnta ery Hod the hydeoias of Bedetones 619 586 Te acdcataaed rearrangement of Dll 623 587 The oxdstiveiydrolyas af mlieonate <a ram seemiry nitroatkones 623 S88 Methods forthe protection of the carbonyl gu tn naohsdes and Keto 23 5.2 DIEAREOM. COMPOUNS 25 ‘Srnctne 426 58112 Diowbuoy! compounds 627 52 1kDjenrtme| compounds 632 593 1 Abicarhony| compounds: 635 ‘10 camnmuronares oo Sirature 12 101 Corbahydrate ntercomersons, 642 S193 sua S104 AUPHSTIC CARSORYLIC ACIDS oy Siructre Go ‘Susamery of prepartie inethads ond ofvetrsyniterde sitategice 864 ‘Specroscopisfectures 866 SILT Oxidative methods 667 S102 Updeotyin af gl cyenides 671 SILS Carbasvltion of Grignard reugenes 673 SCA The Arndt Fister mathe 8 SULA Blestrolite (andl) counting. 677 SING Methods using dicthel malonate 620 SULT Tae spmtsi of opialy active carboxybe aids 687 5.11.8 Motwods for fhe protection ofthe carboxy! yramp 690 ‘RN2_ CARFOXYLIC ACID BERVATIES a Sirueare 1 ‘Stomary of recrosymbetic stratsgles 692 Spremancop feres 682. 5123 Baer Oe SUPA Add amides 708 AL AUPaRTic mEMLES na Sammacy of preparative methods and of retrocputhvc rateges 710 Spentrscapi features 711 SUS Diuplacomont milk anid Som ono ay] hal S132. Degaesinent ith cite fo man arslanpboushyarazone 712 533 Dehydration of andes and aMloximes 715 e711 om a at Bo an sa 5.184. Cyanocthylnin proves andthe sites 717 SUASTIUTED CAEROXYLIC ACIDS ANIL TRER DERTEATIVES Siractare 118 ‘Shestronsunie fearon 720 SiLAU Habpgene aces 720 S42 Hydroxy aelds and lactones 728 S143 Keo sede and extere 735 54a Aimino acs un peptides. 748 sare LAME Siracare TE ateyaton of omy ne ™ ‘Sammury of prepartine methods and of retroymtheic strategies Ted Spectentapi feature 768 SHS The esplacemem of «halogen by a wibite fon in an alkyl ate Tout 5182 The exidaton of aces and arnes 765: S183 C-Alkglation of eitvoakanes snd other homilogtion procedures. 768 AQIPMATIC AMINES Swactere 768 Sunanary of preparative methods and of retronpntbete strateges 770 Shrernscops featmee 7 AGS Lhe reluete alguien of ammvaia or amines. 76 GA The alksalion afm SAGs nine a 386. Moca troup 74 AUPARTIC SULPHUK COMPOUNDS Srowture 6 Specrosopis forex 789 7.1 Took wad inoctale 787 5.172, aly solghites‘ioetes) nd tilkyeniphoniun, salis 169 S73 Salphonldes and salphones 791 SU74 O,S-Dialiyl ditiocerbnates (anthale esters} 792 ‘UNSATURATED COMPOUHDS S181 Unssturted stcobole 794 S482. Unsutrated cwbonpl componnds 798 S183 avsturated acids aod eters 820 FESOLUTIOW OF RACERATES REFERENCES ™ ne
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