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NO AU mae CoM ered Om a le)eKe)H Wala Ch) (Oe ee Daflbucclar FIO Arkagucrr AlkHHBE oH CAMHOE R-3neKTpOHHOC Tipeneanmie panaxama CHy—CH,— CHy—CH,— CH,— oma nporma CH,—CH,— CH,—CH,— 5 ipa cHs wsorponua CH,—CH,— i= GH emop-6yma CH; CH,—CH—CH,— ws0Gymn CH; ! Ci CH mpem-6ym ‘Henpezeenme paauxasibs CH,=CH— cH ©- cbenma (Ph) CH= Apomaruveckue panuxa:tbt H—CH,— Ove | (ranoren-) Tasorexo- mpousBon- HBIC CHa oparait oO” GpomGexsoa Tiapox- Compra C,H,;—OH ‘ranon Keron c=0 CH,;—C—CH Kap6o- R- 3 5 Sc=0 | nnapHas = poranou (anteror) (Kap6oHn) 0 oO R ch Anwaernaet cuy—cQ, oTaHas (yKcycHbtit ‘abaler¥ia) pee Ps ee Kap6oropsie| CH,COOH Son | ceo | aatcnona | yecycrtan xncaore Doupras 5 Mpoctsie | CH3—~O—C>Hs ®)R—C-RRY eTHAsTHIOBBI aNKOKeH oxbupet =a a zs 4 | . 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B Kure 7aHo YeTKoe pasieneHHe MaTepHiana No ABYM ypOBHAM CTOXHOCTH: o6ueoGpasoBarenbHOMy Ht TIpo*pHIbHOMy. Aloctynweiii 13b1K v3sI0xXeHHs, GSoraTbii WuHOcTpaTHBHBIi MaTepuan, PasHOObpasHble 3as1aiM — BCe STO NOMOXET Y¥ALMCs NOHATS OCHOBEI XHMHH. ‘YueSunx akmoueH p Dexeparbibiit epee Y4eGHHKOB, peKOMEHLOBAHHBIX ‘Mutuicrepcrsom o6pasonanns 1 Haykn PocchiicKolt DestepalHi. BBK 24.2 9721 © Hosowmuckuii W.H., Hopoumuckas H.C., 2008 © 000 «THA «Pycckoe e100 — PC», 2007, 2008 ISBN 978-5-9932-0076-7 Bee mpana samnmernst Npegancnosue Hens He yinsastica, ornusipa- sich Hasan, Kakoil orpoMHetii war cea a opranieckasi XHMHs 3a BpeMsl cBoero cyulecrsonanns. Hecpasrenso Goniue, ouHako, npencTour efi BhepenH. A.M. Bymaepos Kype opraHueckort XiMHH TocrpoeH ¢ Onopoli Ha Te 3HaHMsa, KOTO- Pbie BLI NpHobpenm Npw w3syIeHHH Obwuel HW HeopraHWueckol XHMUM 8 8—9-x u ocoGeHHo B 10-M Kaccax. 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Bomuincrso Heopranuse- CKHX BeUecTB Hezopiow (HE Tops Ha Boalyxe) BonbiruHicTpo opranHyeckHx BemtecTs 2oprow (ropsr Ha Bosayxe) B Heopranieckux coenmHe- HUSX (38 HKOTOPBIMH HCK- JWOUCHHSIMH) BAICHTHOCTS oueMeHTa WHCAeHHO pasta ero crenenu oKHereHUa. Hanpumep: HO, 20? Ht—0275"“No2 BanerrHocts Bonopona I, crenexs oxucnenus +1; BaleHTHOCTS KHCsOpora II, cTeneHb OKHCIeHMA —2; BaleHTHocrs cept! VI, crenenb oKncnenna +6 B womeKysrax opraHi\ieckHx coemmHeHnit BaJIeHTHOCTS yriepona BCerma paBxa IV, a cTe- TeHb OKHCIeHUs| MOXeT NPAHMMATD sHAveHHA or—4n10 +4, Hanpumep: Ltt bpd H H H BavicHTHOCTb BCex Tpex aToMos yrieposa IV, CTeneHb OKCIeHHA KpaliHx aTOMOB yrulepona pasHa —3, a cpemHero — —2 Heopranwyeckve coennHe- HS SIBIGOTCH OCHOBHEIM MaTepualloM HEKHBOR npuponss Opraruyeckne coenHHeHMa sBISLOTCS OCHOB- HBIM MaTepHayloM, H3 KOTOporo MOcrpoeHB! OpraHMsMbl paceHHii 4 KHBOTHBIX (KHBAA mpHpona) °? Sananns 1. Tlepeuncaute ocoGeHHOCTH OpraHMYeCKHX BeLIeCTB B CpaBHeHun ¢ HeopraHHuecKHMUH BeuecTBaMH. 2. O6bacHuTe, NOYeMy OpraHHYeCKyIo XHMMIO BLUIETHIIH B OTENbHbIt pasiien XAMMM. @ 3. B ornuune of Heopranmuecknx BenrecTs opranMyeckne a) XOpOllo pacTBopsloTes B BOE ) pawlaraioTca Ha cBeTy ©) nerye Bosayxa 1) NouTH BCe ropsT 1 @4. Monexynaprioe ctpoenme uMetor ce BemiecTBa HaGopa a) CaCl, SO,, CH,,C,H,OH 8) CH,, HCI, NaCl, CO, 6)C,H,, NH;,CH,COOH, CO, _r) C,H,0H, Ca(OH), NH;, SO, (@5. Hemonexyasproe crpoeHve umeror Bce BeulectBa Ha6opa a) CH;COONa, Ca(OH),, NaCl, MgO. ©) MgO, C,H,OH, Na,SO,, C;Hs 8) Ca(OH), CH,COOH, CH,, KCI 1) C)H,, CO,, KCI, CH;,COONa @ 6. Han6onutee konnyectso BeutectBa (Mom) conepxar 200 r a) CO 6) H,S 8) CH, 1) CH § 3. Teopua xumuyeckoro crpoeHua oprannyueckux Coegunennii A. M. Bytneposa ! Tloemopume: 2nekrponHple 4 CTpyktypHbie (opMysbI coenHHeHHii, 3HaYEHHE NepHoOnMyeckoro 3aKOHA. Npeanocbinkn BosHnkHOBeHKA Teopun K cepenune XIX b. oprannueckas xAMus MpencraBaaa coborK cymMMy Pa3pO3HEHHBIX CBELEHUI 0 KOOCCABHOM KOHYECTBE OPraHMYeCKHX CO- enuHeHHit. Kaxaoe HoBoe BellIeCTBO H3yyaIv HE3aBMCHMO OT PyrHx. bilo U3BeCTHO MHOFO (pakTOB, KOTOPbIe YUeHBIe He MOTH OOBACHHTb. Hanpumep, novemy yriepog oOpasyet Takoe GONbILOe KONUYECTBO CO- €MHHEHH (BAM HSBeCTHO, 4TO OpraHHYeCKHX BELECTB 3HadHTEbHO Sombie, 4eM HeopraHHyecknx); NoueMy BeILeCTBAa, UMEIOLKE ODKH H TOT 2K€ KaYecTBeHHbIii H KOAMYECTBEHHBIi CocTaB, paxIMYaloTca 110 CBOHCT- bam. Takne weuecrsa 1. Bepuenuyc Ha3Bai wsomepamu. HanpuMep, u3- BECTHBI€ BaM IIOKO3a KH cppyKTO3a KMEIOT OMHaKOBbIit COcTaB CH 20, HO pasiMunble cBoiictBa. HescHo 6bin0, KaKOBa BANeHTHOcT yrnepona 10 B OpraHUyecKHX COeAMHEHHAX, TaK KaK KOMYCCTBEHHBIM COCTaB MHOFMX CoemMHeHHit, Ka3a/lOCb, H€ COOTBETCTBYeT BaleHTHOCTH yrviepona: CoH, CjHg, C)H,, C)H, 47. 1. MHorve yueHble orpHuai BOSMOXHOCTS N10- 3HaHMs CTpOCHUA MoneKyI, a 3a4acTy!o He NPUSHaBAH H peambHoro cy- L\eCTROBAHMA MOJIEKy/ K aTOMOB. OAHOMY H TOMy Xe BeLecTBy Npunu- CBIBAI He ORHY (POPMYIIY, 4 CTOMLKO, CKONILKO pa3IMYHbIX NpeBpallleHHit OHO TipeTepnieBaio, HalpHMep yKCyCHOH KHCAOTe B 3ABHCHMOCTH OT Npo- ABASEMBIX XMMMYECKHX CBONCTB NIPHMMcbIBaM Ba DecsTKa ¢bopMyll. Baecte c TeM pa3BUBalOllIMecs MPOMbILLICHHOCTb H TOproBis Tpe6osanu MONYYEHUA BELIECTB, KOTOPLIX He MOMIa MaTb YeOBeKy Npupona. Tak, TEKCTWIbHOM MPOMbILLWICHHOCTH HYKHbI ObLIM KPaCHTesIM, MENMIMHe — JKAPCTBEHHbIe Mpeniapatbl, HEOOXONHMO Olio COBepIeHCTBOBATE Me- TOMEI NepepaGOTKH CesMLCKOXO3sIHiCTBEHHO! NponyKUMH HT. 0. Ho pasev- ‘THIO HOBBIX METONOB CHHTE3a OPraHHYECKHX BeLECTB Mela HemocTa- TOYHOE TeopeTHYeCKOe OGOCHOBAHHE NpakTHYeCKUX 3alla4. B S0-e rr. XIX b. Gbi1H chenaHbl BaxXHbIC OTKPLITHS, KOTOPbIe COsLaTH MpeAMOcELIKH Wis paspaGoTKH TeOpHH XHMHYeCKOrO CTPOeHHA OpraHH- 4eCKHX CoeqHHeHHii. Auriuiicknit XuMuK 9. DpaHkSHT BEN NOHATHE «BaIeHTHOCTb>. PasBuBasl yueHHe © BaeHTHOCTH, HeMelIKHe XHMHKH ®, Kexyne 4 A. Komb6e o60cHoBai YeTbIpexBaleHTHOCT yriepona B OpraHuyecKUX coenuHenvax. Llotnanackuii uccreqosatenb A. Kynep 4 HemenikHit XH- MuK ®, Kexysle He3aBHCHMo sipyr OT Apyra ycTaHOBMAK crocoGHocTb aTo- MOB yrvlepOjla COMHATECA [pyr Cc Apyrom c OOpa3z0BaHiem ueneii. B 1860 r. B Hemenkom ropone Kapacpys Ha MexayHaposHoM cbesye XHMHKOB ObUIM OKOHYAaTEHO OMIpeNeseHbI NOHATHS «ATOM» H «MOJIEKYsa>, Onnako 970 6bUIM NH OTENBHBIE cakTEI, Meu. A HyKHa ObuIa TeO- PHA, KoTOpad MOrsIa Obl He TONbKO OGbACHATb HAKOMMBILIKECA thakTbI, HO Anexcannp Muxaiinosus Bytnepoa (1828-1886) Pyccxni xumisk, npocpeccop KasaHcKoro mu Nerep6yprcko- FO yHnBEpCHTeToR, akaneMMk POCCHIICKON aKANEMMM HayK, ‘TBOPeL| TEOPHM XMMM4ECKOTO CTPORHIA, CTABLUEH dbyHAa- MeHTOM OpraHi4eckoit xnMiNn; CosaTenb KpynHeliWwelt OTeYeCTeeHHOA WkONbI xAMMKOB-OpraHnKos. A. M. Byt- nepoe Hanvican «Beezenne k NonHOMYy M3yHeHINIO Opra- HMYECKON XHMM> — NepBOE B MCTOPMM HayKN PykOBOn- TBO, OCHOBAHHOE Ha TEOPHN XHMUYECKOTO CTPOeHHAA. Webi npenckasan v wayann v3OMepHio MHOMHx Opra- HMYECKHX COeAMHeHMI, peakuio NONMMepusaliMn, 3a- TOXUN OCHOBE CHHTESA BLICOKOMONeKynAPHbIX COepM- HeHvi4. CunTesmpoBan MHOrve OpraHiueckne seuyecTea. iW H Mpelicka3bibaTs CBOHiCTBA H CTpOcHHs BeLllecTB. Takylo TeopHio, ONMpacb Ha TPys1bl CBOUX pe ALUECTBEHHUKOB, CO31a/ BhUAIOUIMiicA pyccKHii XAMHK Agexcanap Muxaiinosny Bytiepos. OH Gb yOexKeH B TOM, TO aTOMBI B MOJIEKyJ1aX COEMMHEHBI B OMIpeseNeHHOM MOpANKe, 4TO CTpoeHHe Moze- KyJIbI TO3HABAEMO H YTO AMEHHO OHO OnlperesiseT CBOHCTBa BeLIeCTBA. OchosHble nonoxeHus Teopuu xuMu4ecKoro CTpoeHHA opraniyecknx coeguHeHnit OchosHble Wien cosnaHHoOH uM TeopHu A. M. Bytnepos H310KH B Nokane «O XHMHYECKOM CTPOEHHH BELICCTBA> Ha Cbe3Ie HEMELIKHX ecrecrBoucnbirarenei 4 Bpaveii B LUIneitepe 19 centa6ps 1861 r.: «...xH- MHNCCKasl HaTypa CIOKHOH YacTHUbI ONIpenesAeTCA HaTypol QIeMeHTap- HbIX COCTABHBIX YaCTeii, KOAM4ECTBOM HX H XMMHYECKHM CTPOeHHEM>. C ucnonb30paHHemM coBpeMeHHoi TepMHHONOrHM cyTb TeopHi A. M. Bytilepopa MOxKHO BbIPasHTb B BHC HECKONIBKHX MONOxKeHHit, 1. Amows 6 monexynax opeanuuectux eewecme coedunent: meaKdy coboit XUMUMECKUMU CBABAMU 6 ONpedeneHHOil NocnedosamenbHOCMU CozNaCHO UX eaneHmuocmu. Tlopanok cea3v aToMos B Mosekyne Byriepos Ha3Ban xuMuneckum* cmpoenuem. XUMMYecKoe CTpoeHHe MOMeKYsIbI OpraHUYecKOro COeMHHEHHA BbIpa- 2xaloT Cmpykmypuoit opmyaoit (pasvepHyToit HU CoKpallleHHOll), KOTO pad AA WaHHoro BeWecTBa ABIAETCA eOUHCMBeHHOU. B pasBepHyTOH dop- Mysle YepTOUKaMH OGO3HayAaIOT BCe CBASH (T. €. YHICO YePTOUeK PaBHO Ba- JIEHTHOCTH aToMa), a B COKpallleHHOH — TONbKO CBASH ME@KZy aTOMaMH yriepona. 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Teopia crpocHs opraHMuecKHX CoeMHeHHii NOSBONHa yaeHbIM: e32naHymb Ha MOAeKyAy KaK Ha cucmemy, B KOTOpOM cyuiecTByeT CTporMit NOps10K BASE MeXsy aTOMaMH, MOKa3aTb BO3MOXHOCTb NO- 3HaHHA STHX CBA3ei; cuctmemamusuposam BeCb HaKOTIMBLIMiicA MaTepHall H o606qumb O- CTWKeHMA B OOaCTH OpraHHyeckoit XHMHU; HE TONBKO O6sscHamb V3BECTHbIe B HayKe ¢pakTbI, HOH npedcKasbi- 6am (npozHosupoeame) cile HeH3BECTHbIe — CYIeCTBOBaHHe HOBbIX Be- AeCTB, HX CBOHCTBa M NyTH CHHTE3a. Teopus A. M. Bytneposa ycrpanwaa xaoc, cyttecrBopaalunit B opra- Heveckoli xuMHH. Henapom B nicbMe K M1. Beprieanycy B 1835 r. . Bé- Jlep Tak XapakTepv30Ball MomOxeHHe en: «Opranvyeckas XHMUs MOET ceiiuac Koro yronHo cpecrH c yma. Ona npecrapnseTca MHe apemy4HM ACCOM, TIOAHDIM YAMBHTEIbHbIX Bellel, GesrpaHHHOH yalleli, 43 KOTO- 15 poli Henb3s BbIOpaTbca, Kyla He OCMENMBACLUBCA NPOHUKHyTb>. Teopus XHMHYCCKOFO CTPOcHHs! OObACHWIa CyLHOCTb ABIEHHA H30MepHH. Oc- HOBBIBaACb Ha paspaOoTaHHOii HM TeopuH, A. M. ByTsepos npencKasai CyllecTBOBaHHe HEH3BECTHEIX B TO BpeMA OPraHHYeCKHX BelecTB. TaK, To 1861 r. 6bINO H3BECTHO JMUIb OAHO BeULECTBO cocTaBa C,H j)— GytaH. A. M. Bytepos npencka3ai1, 470 LOKHO CylleCTBOBATb eLile OHO COeHH- HeHHe c maxoli se MonexynspHoi opmynoil, Ho ¢ Opyeoit nocnedogamenbHo- cmet0 coeduxeHua amomos 6 MoneKyne. FTO BEULCCTBO OH HasBan H306yTa- HOM (T. €. H30MepoM 6yTaHa) H MpesIoxKW MeTON ero CHHTe3a, KOTOPbIHi caM BCKope H OcyliecTBHI. MonyseHHoe KM BeLIeCTBO HMEN0 TOT Ke CO- crab CHyo, Ho Apyrue cBolicrBa, B YacTHOCTH, Gonee HaKyIO TeMTIepaTy- py Kunenus: CH;—CH,—CH,—CH, .{C GYTAH (fy = 0,5 °C) MIOGYTAH (fen = —U1,7 °C) PaccmarpuBad BO3MOxHOe CTpoeHKe nenTaHa CsH,,, A. M. Byepos NPHUEN K BEIBOMY, ITO HOJDKHBI CyLIECTBOBATb TPH yrsI¢BOROpoLa TAKOO coctaba. Boe 97 BeulecTBa ObLTH MOyYeHbI ero YAeHHKOM M. J]. JIBBOBBIM. Tak 6b HaligeHbI yOequTeNbHbIe MOKa3aTeENLCTBa CNpaBeANHBOCTH reopuu A. M. Bytiepona. Teopua crpoenna cnoco6ctBopala GypHOmy Ppa3BHTHIO CHHTE3a pa3- Hoo6pasHbIX OpraHH4ecKHX BeLeCTB: eKapcTBEHHbIX NpenapaTos, Kpa- CHTeNeH 2A TEKCTHIbHOM MpOMbILLUICHHOCTH, HCKYCCTBCHHbIX BOJOKOH UT. a. Cefiyac 6e3 NPonYKUMH OpraHhyecKoro CHHTe3a He MOXET CYLIECT- BOBaTb HU OLHA OTPacib HapOLHOTO XO3siiCTBa. Kax u npensunen A. M. Bytiepos, Teopua XAMHYeCKOrO CTpOeHHA He octalach Hev3MeHHOi. JlanbHeiiiiee ee pasBUTHe LWIO MaBHbIM 06pa30M. Mo JByM HanpagieHusM: W3yYeHHe azexmpoxHozo cmpoenua (cpopMu- PoBaHHe 3/leKTPOHHBIX NpeACTAaBCHHii O mpHpose XAMHYECKHX CBA3ei) npocmpancmeennozo cmpoeHun MoneKya (peanbHOrO PacnhO1OKeHHA aTo- MOB B TIpoctpaHcrse). Yxe B 1874 r. cppakuy3scKHii XAMHK XX. Jle Benb u Hugepmanicknit yaenbiit 1. Bart-Tod paspaGoTaiH OCHOBEI cmepeoxu- MUU — HaYKM O TIPOCTPaHCTBEHHOM PacriolOXeHHH aTOMOB B MONEKys1aX. Teopusa XHMHMECKOrO CTPOCHHA BLIABMa TIPHYHHbl MHOroobpa3sva OpraHwyeckHx CoenHHeHuit: 1. 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Onpeaenute paneHTHOCTh M cTeferHb OKHCIeHHA yrepona no opmyzaM coequHeHuii 4 pacnovloxuTe UX B NOpsaKe BOSpacTaHHs cTe- TeHH OKHceHHs atToma yruiepoma: C;Hg, CH,, CH;Cl, CH,0H, CCl, 3. Ms06pasute crpykTypHbie (bopMys1bI TMAPOKCHa HaTpHa vl THI- poKcuia cepbi(VI) — cepHoii KHcnOTbI — H YK@KUTe, Kak BIMAeT TIpuposla aToma, Cc KOTOpbIM CBA3aHa FMApOKcorpymna, Ha CBOlicTBa STHX COeHHHEHH. 4, Pacnonoxure opmysbI B MOpsAAKe yBeNUYeHUA CHI KUCIOT: HCIO,, HCIO, HCIO,, HCIO,. O6nacHure NoBpMueHHe cumbI KUC- JIOT B341MHEIM BIMAHHEM aTOMOB B MOsIKyIIe. («) 5. Ha MoMenrT cosiaHua TeopHl XHMU4eCKOrO CTpoeHHs opraHHue- CKHX COeKHEHH OTCYTCTBOBAIO a) yueHHe 0 BasleHTHOCTH 6) mpegcTaBreHne O CoeMHHeHHH aTOMOB yrulepoza B Len B) pasrpaHnycHHe NOHATHH «ATOM» H «MONIeKysIa> 1) MOHATHE 06 3/1eKTPOHHOM CTPOCHHH aTOMOB 3/IeEMEHTOB 6. CpaBHute pouib UIA HayKH NepvogMueckoro 3aKoHa J. HW. Menie- Jieeba HW TeOpuK XnMMYECKOrO CTpoeHHa A. M. Bytneposa. 2 Opranmoceas xmas. 11 xn § 4. Knaccudukauna peakyni B OpraHnyeckon XuMUn ! Tlosmopume: knaccudpuKaumo Hi Teriosble apekTbl XHMHYCCKHX peak- Ui, BIIKAHHE TIpHpOLb pearHpyrOlHX BellleCTB Ha CKOPOCTb peaKUHH. PeakWHH OpraHH4ecKHX COeLHHEHHH MORYHHAIOTCA TEM Ke 3aKOHaM, 4TO H peakUHH HeEOpraHHYecKHX BELECTB, HO AMEIOT HEKOTOPHic OcobeH- HOcTH (cxema 1): ¢ B PeakLMAX HEOPraHMYECKHX COCAMHEHHIi YacTO yyacTByIOT HOHbI, NosTOMy peakHH MPOTeKaIOT OveHb Hbicmpo, UHOzOa MeHOBEHHO, NDU KOM- Hamuoii memnepamype; Cxema 1 Cpabrenne XHMHY€CKHX peak ¢ yuaCTHeM HeOpraHH4eCKHX H OpraHHYeCKUX BemIeCTB PEATEHTbI Heoprariueckne coemnenia Oprannueckne coenuHeHHia v = Beuyectaa ¢ HORHBIMM H TIoAp- Bemecrsa c MaionionapHEiMnt HBIMH KOB@1EHTHBIMH CBSI3SMIL H HeTIOSIpHEIMH CBSI3aMu. v y Beuecrsa nemonexyaspHoro Bemtecrna MoneKysipHoro crpoenna ctpoenua 22 Y Bsanozeticrayior HoHt Bosmmoneficreyior wonexyma | Y y Peakuiin nporexator 6bicTpo Peakun nporekaior MesuieHHO. M pH KOMHATHOH Temtiepatype Zs yexoperus Tpe6yeTcs noBbi- CHT TeMnepatypy, YBeAMIHTS JABIeHMe, BBECTH KaTaTH3aTOp Bat* + SO? = BaSO,L ‘cu, + 20, ++ Co, + 2H,0 CH,OH+CH,COoH 248%, —+ CH,COOCH, + H,0 18 ¢ B peaKLMAX OpraHHyecKHXx COCAHHEHHH, KaK MpaBMO, ydaCTByIOT MOJICKYJIbI; TIP 9TOM MPOHCXOLHT Pa3spbIB ONHHX KOBAICHTHBIX CBASEH H o6pasopaHve Apyrux, Takve peaKMl MpoTeKaloT MeMIeHHO, H JIA HX yc- kopeHus TpeGyeTcs noseicums memnepamypy, uHoz0a yeeauuumb daenenue, obaeum> Kamaausamop. Nlostomy B ypaBHeHUsXx peakuMit c yuacTHem op- TaHHYeCKHX BeLIECTB, KaK NpaBHlo, yKasbieqiom ycnosua WX TIPoTeKaHUs; ® peaKUMH OpraHH4ecKHX BeLECTB OOLIYHO COMpoBOxAalOTCs TOGOU- HBIMH MpOleccaMH, NOSTOMY BbIXOL LeeBOrO NponykTa HH3KHH (MHOra mexee 50%); @ PeakUMH OpraHH4eckuX CoOeMHeEHH NpoTeKaloT, KaK MpaBusio, BHECKONBKO CTaMit Yepes O6pa3s0BaHHe NPOMEXYTOYHBIX COCAMHCHHI, nogTomy B OpraHHyeckoii XAMHH OOpalllaloT GoNbUIOe BHUMAaHHe Ha Me- X@HU3M Npomekanun peaxyuu. Mexanuzm peaxyuu — amo nocaedosamessnocms 92emenmapnex cmaduil, “epes Komopwie npoxodam peazenmot, npespawmance 6 npodyKmet Peaxyuu. Tlo MexaHu3my pa3pbipa KOBaIeHTHOM cBA3H pazIMYaloT peaKWHH PalWKaNbHble HW HOHHBIE. Paduxaseneie peaxyuu viyt c roMonuTH4eckvM (cBobonHOpanKanb- HbIM) Pa3spbIBOM KOBaTeHTHON cBA3H. IT1pH 3ToM OOLiaa Napa 31CKTPOHOB JeMMTCA TOpOBHY (CHMMETPHNHO) Mexkay ABYMA YacTHLlaMH, KaxKIaA 43 KOTOPEIX NouYAaeT TO ODHOMY HechapeHHOMy 3/1eKTPOHy: B hy wt Ao +008 cBo6oansle pannkansi YacTuupt, o6pasyioulveca B pesysbTaTe TOMONMTHYeCKOrO paspbIBa CBA3H, Ha3bIBaloT caob00ntLmu paduKasamu — 3mo HelImpanbHble amoMbL Wau epynnbl AMOMO6 C HECnapeHHeiM aAeKMpOHOM. Cso6omHile pagHKarbi O1eHb peakUHOHHOCNOCOOHEI, OHH cyllecTBy- 10T JIMIDb MWUIKOHHBIe M DaxXe MHJUIMApAHble 0s CeKYHIbI (T. €. B TO MIHOBeHHe, KOTa MPOKCXOAHT pa3pbIB CBA3H) H GbICTpo BCTyMaloT BAabHeliwue Mpespalenus. TakoMy pa3pHBy NOsBepraloTcsa Henonap- Hole WIM ManononspHEle Koeanenmuxwe cenzu (C—C, C—H u ap.) nog aei- CTBKeM CBeTa KJ BICOKOM TeMNepatypbi. Honnsie peaxyuu wayT c retepoMTHYeCKKM pa3spbIBOM KOBQICHTHOH cpa3n, B 9TOM Cily4ae CBA3YIOUIAA 31€KTPOHHas Mapa MepexOgHT K ODHO ¥3 YaCTHL, KOTOpad NpeBpallaeTCA B OTPHLATesIbHO 3apsXeHHbIi HOH (aHMoH); BTOpad YacTHuA, JIMUIMBLIMCh 3eKTPOHA, MpeBpauyaetcs B r0- JOXKMTCABHO 3apsKEHHBI HOH (KaTHOH): Aj? Bo— At + 2B KaTHOH aHMOH e 19 Takomy pa3pbiBy NosBepraioTcs MoampHbie U Nezko NoAspusyemble Koea- aeHmuvie censu. OGpasoBaBuivecA W3 MONEKYsJI OpraHHYeCKHX BELECTB HOHbI Tak Xe, KaK H CBOGOMHBIE palMKalIbl, ABLAIOTCA NPOMEXYTOYHBIMH YaCTHUaMH; OHM CYLIECTBYIOT TOKO B MOMEHT peaKUMH. STAM OHH OT- JIMYAOTCA OT HOHOB, O6pas0BaBLMxcA Np AMCCOLMALMM HeOpraHH- YECKHX BEIECTB. ITH MOHBI NPHCYTCTBYIOT B pacTBOpaX NOCTOAHHO — JO peakuu Mi mocmle Hee. Jaa HavGonee pacnpocrpaHeHHbIx MexaHv3MOB peakUHii B opra- HHYECKO! XHMMH HCHONL3YIOT CHMBOJIBI, COCTOALIME 13 JIBYX TIporc- HBIX 6YKB, OHA 3 KOTOPBIX NOMeLaeTCA B HWKHHit HHAeKc. Hanpu- Mep, PeaKLMM FAIOTEHMPOBAHHA MPeMCBHbIX YIEBOLOPOLOB Mpo- TeKaloT NO MexaHH3My Sp, 4TO O3HAaeT PalMKa/IbHOE 3aMeLLEHHe: S — substitution (samemerme), R — radicalic (panuKan). Peakumn c y¥uacTvem opraHHuecKHx BeLeCTB paCCMaTPHBaIOT Kak aTa- Ky cy6cmpama peazenmom. Kak npasuao, cy6crpat Gore croxrI0e 1 CTpoeHHo BeulecTBo. ECs 43 ABYX HCXOMHBIX BELECTB OHO OpraHH- yeckoe, a Apyroe HeopraHMyecKoe, TO cy6cTpaTOM CuMTalOoT OpraHH- MHeECKOE BELECTBO. Peakunn OpraHWYeCKHX BELIECTB MOKHO KiaCCHHUMpOBaTs M110 ‘TEM Xe MpH3HAKAM, TO H B HEOpraHH4eCKOit XMMMH, TOKO C HCNOsE30- BaHHeM B pale cay4aen CheuMdH4eckHnx HaspaHinit. Tak, peakUMH CoeaH- HeHMS B OpfaHHYeCKON XMMHM Ha3bIBaloT peaKUMAMH MpPHCOEAHHEHHA, peakUWM pasiOxeHHA — peakUHaMH oTIeNJeHHA (937MMHHHpOBaHHA) ura. °? Sapanna 1. 3akonunre ypaBHeHMa XHMMYECKHX peakUHii H MeTONOM 37IeKTPOH- Horo GaslaHca pacctaBbTe Ko3ppuUMeHTbI. YKAKUTE OKHC/MTEIb H BOC- CTAHOBMTENb, NPOUECCHI OKHCIIEHMA H BOCCTAHOBICHHA: a) NH; + 0,—; b) H,S + O,—+; 6) C,Hg + O,—+; r) CsHy + O,—+, 2. Hanmuinte MonekyyApHbIe, NOJHbIe M COKpaLeHHbIe MOHHO-MOre- KYAApHbIe ypaBHeHHA peakunit Heitpanusauyn axoTHO! yKCyCHOH KHCJOT. Ykaxue, B Kakoii #3 HUX yuacTByeT OpraHHYeCKOE BELUICCTBO. Pasgen! YT NEBOAOPOAbI OsHakoMIeHMe C OTIEIbHBIMM MpeACTABHTEAMM OpraH4eCKHX Be- leCTB HauHeM c yreBonoposos. M3 kypca xMMuu 9-ro Knacca BbI 3HaeTe, uTo yenesodopodes — 3TO npocTeiitiine No KayecTBeHHOMY COCTaBy opra- HMYECKHE COCAMHEHMA, MONEKYIEI KOTOPbIX COCTOAT TOBKO 13 aTOMOB yenepoda u eodopoda. B 3aBMCMMOCTH OT CTPOCHHsA YINepoAHOTO CKeAeTA YIVICBOLOPOAbI NompasiiensoT Ha ayukauyeckue (anuamuyeckue) 4 KapGouuKauneckue. B sapvicvmoctn or THMa cBa3eli MexXAY aTOMaMH YTIepolla YFIEBOLOPOABI jesat Ha npedensnwe u Henpedenbuute. Tnasa 1 NPEAENbHbBIE YYNEBOAOPOAbI Mpedensneie yenesodopods: — 370 yrieBOAOpOnbl, B MOsIeKyyIax KOTO- pbIX Be TOMB! YIVICpOLla COCIMHEHbI MEKAY COBO! OAMHApHOii (0) cBASBIO. Tlpeneabiible yrneBosoponet C He3aMKHYTOM LeNbIO ATOMOB yrvIepoyla Ha- SbIBAIOT @iKanaMu. § 5. SnexTponHoe uv npoctpancTBeHHOe cTpoenne ankaHoB ! © Hoemopume: ru6pwavzaunio aTomHbix opbuTaeli, reomerpHyecKHe (popMBI MonleKysI. Mpoctetimii npencrasutes» alkaHos — meTaH CH,. Paccmorpum cTpoeHne ero MonekyyibI. BI 3HaeTe, YTO ATOM yreposla B BOSOYKEHHOM COCTOSHMM Meer YeTLIPe HECMapeHHbIX 31CKTPOHA — OAH 2s-3IeKTPOH Mt TpH 2p-anekKTpoHa — H 4YTO B MOJIeKysI€ MeTAHa ATOM yrieposa Haxo- AMTCA B CocTOAHMH sp3-rvGpransaunn. YeTbipe oAMHakoBbie rMOpHAHBIE op6vTain pacnoyioxeHbt nog yrom 109°28' apyr K Apyry M HanpaBieHbt K BepuIHHaM TeTpas/pa, B LEHTPe KOTOPOTO HaXONTCA Apo aTOMa yTyIe- 21 ® @ 4) ‘ a 6 Puc. 1. OGpazopanive HMMYECKHX CBASeH B MoeKYsIe MeTaHat a — veruipe sp*-16puabie opSurann atoa yriepona H Yerbipe 1s-opGHTanH aToMos Bonopoila; 6 — Tetpasupyeckaal MoeKys1a Metal; ¢ —‘TerpasapHve- ckoe Hantpannenie ceazeli C—H 8 monexyne MeTatia pola. Tpv Tako pacnonoxeHnu op6uTaI MaKcuMalbHO yaaneHbt Apyr or apyra (pu. |, a). O6pa3zoBaHve KoBaeHTHBIX CBaA3eit C—H nponcxognt 3a cuet nepe- KpbipaHa YeTbipex sp*-rHOpHAHbIx opouTarteii aroma yrnepoua Ht 1s-op6H- ‘Tavteli YeTEIpeX aTOMoB Boropona (puc. I, 6). B o6pasosasulelica Mosekyne MeTaHa spa aTOMOB Bogopoda seat B BepLUMHaXx Terpagapa, ATMHa BCex cBa3eii C—H onMHaKopa u paBHa 0,109 iM, BaneHTHBIe yrnbi Mexay cBa3amn C—H coctapamor 109°28’ (puc. 1, 6). Boe cas B MonleKyse MeTatHia o6pa3yiorca 3a cueT nepekpbi- Balin opOuTaei dar nunuu, cocdunstoweii dpa ® amowmos. Nonobrbtiit BY CBA3H, KaK BaM W3BeCT- HO, HaSBIBaIOT 6-céx3b10. Terpagapu4eckoe crpoerine MoseKyibi MeTa- Ha HesaBHCHMoO JIpyr OT apyra ycTaHoBHIM (ppaH- uy3cKHH XMMUK OK. JIe Benb 4 HunepmanacKnii xumuk A. Bart-Todep B 1874 r. Crpocrine Monekysbt MeTaHia MOKHO BbIpa- a S3MTb 3ICKTPOHHOH (a) HM CrpykTypHoii (6) op- MysiaMit: H Io Heston H 6 a 6 Puc. 2. Mose Mome- “roGbi Haris1HO npencraBuTb npocrpancr- KysIbI MeTaHa: BeHHOe CTpoeHMe MeTaHa M Apyrux opraHHue- @—wapoctepxHeBaa; cKYX COeMMHeHMi, HCNOAb3yIoT WapocTepxKHe- 6 —macurrabuas BBIE H MaCLUTaGHBle MONeNIM MOseKysI (PHC. 2). 22 LJapoctepxkHeBble MO/eIH CTPOAT M3 WapHKOB, AMUTHPYIOLMX aTO- Mbl, # CTepXHeii, MMUTHPYIOIMX XHMHYECKHE CBA3H MEXy HHMH. OHH Har/IAAHO OTpaxator NPOCTPaHCTBEHHOE PAaCniOsOKeHHe ATOMOB B MOsIe- Kysl€, MOKA3bIBAIOT TIOCENOBATEABHOCTS MX COENMHEHHA, HO HE na\oT TipeacTaBacHHsA 06 OTHOCHTeENBHBIX pa3Mepax aTOMOB H MEX bAEpHbIX pacctosHnsax. B peanbHoi MOJeKysIe aTOMbI He HaXOMATCA TaK /aleKO ApyF oT Apyra, Kak WapvikH Ha Mose, OHM TIOTHO yMaKOBaHbl. Bone peatbHoe npeficranicnne faiot MacurTaGHble MonesH (momen Crwapra — Bpurne6a), B KoTOpbIx JeTaM, H306parkaloulive aTOMbI, BbI- TOMHEHEI B ONpeseNeHHOM MacuuTaGe NO OTHOLWEHHIO K JeCTBUTeEIBHEIM pasMepaM. Take MOJEJIM MO3BONHIOT 3pMO NpeACTaBHTb MOJIEKysy Op- TaHHYeCKOTO BeUeCTBa (OGbEM H OTHOCHTE/IbHEIC pasMepbi ce yacTeii). B Moviekyle STaHa XHMHYECKaA CBASb MeXKily ATOMAMH yriepoyla OGpa- 3yeTca MepeKpbIBaHHeM DByx THOPHEHLIX sp’-opOuTaneii (nO OLHO! OT Kaxk0ro aToMa) (puc. 3). B oGpazopabuleiicn MoneKys1¢ 3TaHa CCMb KOBA/ICHTHBIX O-CBASCH, H3 KOTOPEIX LecTb — 3TO cBa3v C—H u ona cBasb C—C: a 6 6 Puc. 3. CrpoetiHe Mozekysibi 9TaHa: 4 — o6pasopalive XAMHYECKOH CBASH MEKAY aToMaMH yrlepona M BoxOpoNa; 6 — wapOCTepxHEBAA MONCH» MOEKYsIBI; 6 — MacuITa6Has MOLIeb MONEKYIIbI 23 TaGauya 2 Kosmuectsennbie XapaktepucTHxu casei Bun ceasa | Alawna, um ‘Suepras, KDK/momb ] Tloaspnocts, cc | oos4 353,6 ~-Henosspuas CH 0,109 4179 Caa6ononapraa Tak kak ru6puniibte op6uTaiH aroMos yrnepoa Harlpapnertbi K Bep- ulnHaM TeTpazitpa, TO B MONeKysie nporiaria CH, BAIeHTHEIH yron paBeHt 109°28', Kak 1 B MOvIeKyyle MeraHa (puc. 4). Ton Takuan oke yrnamu mpH- COCAMHAWTCA B MOJIeKyyaX APyMMX aKaHOB ‘eTBepTbli, naTbii Wn NOCIEAYIOMINe aTOMbI yrVIeposa, OSTOMY yrepomHaA Len’ NpMHuMaer suesazo06pasnyro (popmy. B anekTpoHHEIX 4 CTPYKTYpHBIX cbopmyslax 3TH YFUIbI He NOKaSbIBaIOT: CH,—CH,—CH,. Takum 06pa30m, 6 npedenbHtix yenesodopodax: ¢ aTOMbI yrmepora HaxonsTca B sp}-rMGpHAHOM COCTOAHKN; * BCe CBASH aTOMa yrvIeposla HanpaBNeHbI K BeplMHaM TeTpagnpa; ¢ BCe aTOMbI yrneposla coenuHeHbI Mexay coGoii OAMHapHOii (oc) CBASHIO; ¢ ama cBisn C—C cocrasnset 0,154 HM, BAIeHTHBI yro 109°28'; ¢ HadMHas C nportata C;Hg, aToMbl yrsiepona pacnomoxkeribl He 10 Npamoii Mun, a 3MrsarooGpasHo. 109°28" 6 a Puc. 4. Crpoerme Mostekysibi nporiatia: 4 — Hanpapnenve XMMHYECKHX CBa3eit B MovleKysie; 6 — wapoctep>kHeBas Mone; 6 — MacuuTaOHas Moles MOsIEKYsIbI 6 4 os Jla6oparopHbii orbit (BbiIrIOnHseTCA LOMA). Usrotosnenve mopeneii Monekyn yrneBonopopoB UW ranoreHonpousBogHDix Ucnonpsys naactusimi 1 nepensntible WM MeTasiMueckne cTepxHH, MSrOTOBETe Moses MOLIeKysI. 1. Wapocrep»xtepas Mone MoseKysbI MeTaHa. M3 nacrununa onHo- TO LBETA FIpHrOTOBbTe YeTEIPe LUaPHKa OAMHAKOBOFO pa3Mepa (MMHTHpy- JOT aTOMbI BOQOpona), a M3 MWacTHIMHa Apyroro uBeTa — OM WapHK (umutupyeT atom yrnepofa), aMameTp KoToporo B 1,5 pa3a Sombie npe- Abylyuinx. Ha nopepxtocTu Wapnka Odabiero pasMepa HaMeTsTe YeTbIpe ‘TOUKH H BCTABLTE B STHX MECTAX CTEpKHH NpHMepHO Now yrI0M 109° or- HOCHTEbHO Apyr Apyra. K cBoOOsHIM KOHUAM CTepkHei npuKpenuTe NeTbIPe M@IEHBKHX WapHka. MBICeHHO 11M NIpK NOMOLIM HHTH CoeqH- HHTe kHeByl0 H MaciuTaGHyto Moflean. M3meHioce 1H MpoctpaHicTBeHHOe crpoeHHe Monekynbt MeTaHa? Kakan Moses Gosee TOYHO nepenaet ee cTpocHHe? 3. Mogeam Mosexya mponana, Gyrana 4 w306yrana. Vis Tpex wapo- CTepKHEBHIX MOMeNeH MONeKy.jbI MeTaHa (M43 Tpex TeTpazzpoB) coGepuTe MOME/b MOJEKYIbI Nponaka, a 43 YeTbIPex — MOEN MOJIeKyJI GyTaHa w3o6yTana. Yka@kHTe, KaKoli 20/DKeH ObITb BaeHTHbIi yron. Mouemy Mosie- kylibI aikaHoB, HaunHas C nporaHa, AMe1oT 3uT3aroobpasHoe crpoeHne? t Saganua 1. Ykaxkue (c nomoubIo cTpeno4yek) CMCLICHHe 3NeKTPOHHO! MIOT- HOcTH (a1eKTPOHHOH naps) B MoneKysax: H,O, CHCl, CO,, C;Hg, HCIO,. 2. B Monekysax aikaHop aTOMbI yrviepona pacnosoxKeHbI a) no Kpyry B) 3ur3aro06pa3Ho 6) no npamofi nun 1) CoeAMHeHbI B LK 3. Onpenenure Bum xuMMuecKoi CBA3H B MoneKysaX aMMMaKa H MeTaHa, COCTABbTE HX SICKTPOHHbIC CbopMysibI H M30Gpa3HTe Cxe- Mbi N€peKpbiBaHHA aTOMHbIX OpOuTaei. VKaxkKHTe, YEM OHM OTJIM- ‘alOTCsI No CTPOeHMO M KaKasl M3 MONIEKY! HenonsipHas. 2s 4. B us6pirKe KHcAopona Coxran 6,72 1 (H.y.) MeTaria. Bbruncante oGbeM MH KONMYECTBO BelllecTBa NOsyYeHHoro OKcuiza yrneporia(IV), ecm BEIXOM NposykTa peakUHH CocTaBIsAeT 95%. § 6. Tomonormyecknii pap, HOMeHK/NaTypa 4 M30OMepua ankaHOB Tomonoruyeckuii pag ankaHoB K npefenbybim yrneponoponam oTHocaT meman CH,, 9mau C,H,, npo- nau C,H, ¥ ap. (ta6n. 3). Paccmarpnpasd coctaB yreBoloposos, BHMM, STO KaKAbI NOcMeAyIOWIM YeH STOTO pala OTIMYAeTCA OT MpebLyLLe- ro Ha rpynny CH. Ta6auya 3 Tomonornyecknii psy mpenembHbIx yreBonOpon0B ‘H @JIKHJIDHBIX PAHKAIOB Hasnanne | Moatexyaspnan | Yncso | meal yenesogo- | dbopmysa anKana | BO3MOKHDIX —MY.1a PaNNKaa ona Have | waomepon | —CyHoyss = Meran CH, I —CH; Merus Oran CH, 1 | —cH, | rus Tponan oH. 1 | —oH, Tportus Byran Cs 2 —CiHy | Byrua Terran CcHie ) 30 | —OyHy Tlerrru (amma) Texcan CHy (5 | = CyHis Texcus Ferrran Cie | 9 —CHs Tents Oxtan CH |B —cH, — | orm | Honan CoH 35 —CHiy Honma Dexan Cpl, 5 CH, Tene | iwosan | Coot | 366319 Cag Siikosus 26 Bewecmea, cxodneie no cmpoenuto u xumuneckum ceolicmeam, Ho omau- uaromuecs Opye om Opyea no cocmagy moseKya na OOHy WAU HECKOABKO zpynn CH), na3tiearom zomoaozamu: TOMOJIOrH ia, CH;—CH, CH;—CH,—CH, ran nponan Tomosorn, pacnonoxeHHLie B nopsake BospacTaHHA Ux OTHOCHTENb- Holi MOJeKYJAPHOH Maccbl, O6pasyioT zomonoeu4eckuii pad. Tpynny CH, Ha3blBaloT 2omanoeuuecKkoll pasHocmero. Ecnv 4vcno aTOMoB yrsiepona o60sHauHTb 1, TO COCTAB BCEX YEHOB TOMONOFHYECKOFO psa wIKAHOB MOXHO BbIpasvTb OGuueH dopmyioit: CyHana2, 221 | Hanpumep, npu n= 7 ankari umeet cocras C,H, — renran. A1kanbt — amo yeaesodopodbi, 6 MoAeyAaxX KOMOPbIX BCE AMOMEI yerepo- Qa naxodamca ¢ sp'-2ubpudnom cocmonnuu, coedunensi memdy coboit moavko O-cenzamu u umerom obwuyro popmyay C,H o_ +42 B mostekysiax npenesbHbIXx yeBoLOposoB, HayMHas C Mponaria, Kaxk- Abii aTOM yruiepofa MOxeT GbITb CBAZAH C O/HHM, ABYMA, TpeMA HIM 4e- TbIPbMA ATOMaMH YTIepomla, NOSTOMY pawIM4aloT aTOMBI YrIeposla: ¢ nepeuuneie (CBA3AHBI TOSEKO C ONHUM aTOMOM yrnepona); ¢ emopuunere (CBA3AHbI C ABYMA [[pyTHMM aTOMaMH yryiepona); ‘¢mpemuyneie (CBAZAHbI C TPeMA aTOMaMH yrviepona); ¢uemeepmuuneie (CBA3AHEI C YETbIPbMA ATOMAMH yrvieposia). Nlepswunpiii = Broprunbiit arom atom Merpeprsineiit Tepsyursii arom arom CH, | GH —CH- CECH CH; _CH, Tlepewannic atomer ‘Tpernunniii arom Heo6xogumo yunTbiBaTb, YTO CBOMCTBA ATOMOB BOsOpona Mi Mpyrux @TOMOB 3aBHCAT OT TOTO, C KAKHM ATOMOM Yryleposa OHH CBASAHBI: C Nep- BMYHBIM, BTOPHYHBIM, TPeTHYHBIM. 27 Ecau yriepomHas enh HopmManexaa (nepaz6emeneHHaa), TO B Heit WMe- 1oTCA TONBKO TePBMYHbIe M BTOPHUHBIe ATOMBI yrnepona. Hanwune Tpe- THYHBIX M (WIM) YETBEPTHYHBIX ATOMOB yruiepofla OOycOBNEHO paseeme- AeHuem yrepoaHon WenH: H,;—CH,—CH,—CH, CH;—CH-CH, CH, Hepa3peTaveHHaa wer pasBeTBieHHas Lent Homenknatypa ankaHoB OrnmuntenbHoit OcobeHHOcTbIO OpraHvueckoii XMMHH AB/IAeTCH Or- POMHOE 4MCIIO COEAMHEHHi, KOTOpbIe MoxeT OGpas0BbIBaTb yriepon. Bo w36@KkaHHe NyTabHMUbl, BOSHMKAIOUeli 13-3a HETOUHIX HasBaHHii, B Ha- CTOSLEe BPEMA NOMBIylOTCA MemcdyHapodHoil cucmemamuyecKoil HoMeHK- famypoil, paspaborasHoit MIONAK — MexkayHaponHbim co130M Teope- THYecKOH MW NpHKaaHoOl xuMuN. HaspaHns, CocTaBeHHbie No npaBwiaM STO HOMEHKaTYpbl, OTpaxkaloT CTpyKTYPy COC¢AMHCHHA, NOSTOMY MO Ha- 3BaHHIO MOXKHO OAHOSHAYHO NpeACTAaBUTb CTpyKTypy HK Haobopor. Ho- MeHKlaTypa aikaHOB — OCHOBA JL Ha3BAHUA MHOTHX OpraHMYecKHX CO- eannennit. Paccmorpy ee nogpobxo. Ha3parine mo6oro ankaHa uMeeT CydbipuKc -aH. Tleppite verbipe wera TOMOTOTHYeCKOTO palia MMeIoT HCTOpHHECKHt CAOXMBLWMECA Ha3BaHHA: MemaH, 3maH, nponak, Gyman. Ha3BaHMa cie- AYIOWWAX YIEBOLOpOOB C HOpMaIbHO! (HepasBeTBAeHHOIt) yrneponHoi UENbIO NPOKCXOAAT OT COOTBETCTBYIOWIMX [PeYeCKHX YHC/IMTEJIbHBIX* coGapneHnem cydbuKca -an. Tak, rpeyeckoe Ha3BaHHe Yona 5 — a Hj —CH,—CH,—CH, «CH ->CH,—CH—CH, w-6yran so6yrax (2-Mer#uinportatt) Bewecmea, umerouue odunaxostiit cocmae, Ho pashoe cmpoenue, Hazbi- eatom cmpykmypnoLmu usomepamu. 3 a 6 Puc. 5. Moen moxexys1 6yraHOB: a — HOpManBHOrO cTpoeHHs; 6 — pasneTanenHioro crpoeHust W3o6ytat 4 x-GyTaH — CTpykTypHble H30MeppI (pu. 5). Ecaw y GyraHa ToabKo Apa H30Mepa, To y neHTaHa C5Hj) ux Tpu, ay renrana C,H, —aepate. Vrnesonopon coctapa CygH,) (eKaHl) Meet 75 W30MEpoB, a 9H1KO3aH CyoH4) — 366 319. CrlenoBaTesbHO, YHC.10 130- MepoB GLICTpo pacteT MO Mepe yBeMYeHMA YMCA aTOMOB yriepona B MOJleKysle yrvieponopona (cm. Ta6n. 3). CpoiicrBa M30MepoB pazIHYHEI (ra6x1. 4). Ta6auya 4 usnueckHe cBoiicTBa H3OMepHbIX 6yTaHOB Dopmynnt ‘Temneparypa, °C Moowep | one a aes | napeas erpykrypnaa ax | + a |__—_|_. 1 Byran CyHig | CH;—CH,—CH,—CH,, -138 | 05 Tas Hoobytan | C,Hyp CHy—CH—CH, |=159,6! —11,7| res | | CH, B ta6n. 5 npweefena cpaBHHTesbHan xapakTepCTHKa FOMOJIOFOB KH M30MepoB. TaGauya 5 (Cpanienie roMo.10roB H H30MepoB = Kavecrmennstit Koamvectacnnmiit Xumarseckoe | Xmmmaveckue cocTaB cocTaB cTpoenne caolicraa | 1 Crone Tomonorop |= Onuuakospliit PasnwuHeiit | ‘CxomHoe Vzomepon | Onunaxoss | Onunakoenit | Pasnwunoe | Pasnwuneie | 32 JL palukasiop Takxke xapakTepHo sBIEHHE H30Mepun. CrpykTyp- Hasl M30Mepus OGycIORNeHa CmpoeHuem yenepodHoeo cKenema VK No- MOKEHUEM HecnapeHHozO aneKmpoHA. ITO NPMBOAMT K YBCAMYeHMIO YNC/la H3OMEPOB M0 CPpaBHEHHWO C COOTBETCTBYIOLIMM aiKaHom. Ha- npuMep, Mporiat #30MepoR He HMeeT, a palMKan Nponwi —C;H, uMe- eT 48a H30Mepa: E 3H, | SL CH,—CH,—CH,— CH uch nporwen wsonponwa Tlo nonoxkeHHio HecNapeHHOro 9eKTpOHa BIKWJIbI KaCCHMUH- pylor Ha: ¢ nepeuxnee (O6pa3z0Bakibl NYTeM OTPbIBa ATOM BOJOPOsa OT nep- BHYHOFO aToMa yryiepofla): CH;— GHs— CH;—CH,—CH,— Nenu orm port i CH;—CH,—CH,—CH,— — CH;—CH—CH,— 6yniur w306yTHA * emopuuneie (O6paz0Balibl IlyTEM OTPbIBa ATOMA BOMOPONa OT BTO- pH4yHoro aToma yryieposia): CH,—CH—CH, CHy—CH—CH,—CH WSOTIporit emop-Gyrun ¢ mpemuuneie (oOpaz0BaHbl NyTeM OTPbIBa aTOMa BOLOPONa OT ‘TPeTHYHOTO aTOMa yriepoa): cH, CH;-C— CH; mpem-6y rw 3 Oprawmeckan Xuan, 11 xn. 33 HaspaHnn 3THx paluKailoe Hal 3HaTb, yTOGbI Ha3bIBaTb yrIeBO- AOposbl cox Horo crpoenua. Hanpumep: GH CH; CH, Ret, 2 5 ie BOM ee CHy—CH,~CH—CH-CH_CH_CH CH-CHs CH, CH, 3.mpem- 6ytw.1-4-va0nponiun-2,5-nuMerHarerttaH Xapakreprian oco6eriHocTs 6-cBa3eii — cummeTpHHoe pacnos0- OKEHHE MaKCHMYMa BIEKTPOHHO MIOTHOCTH OTHOCHTEBHO OCH, CO- eAMHMOUE! sAlpa cBA3bIBAeMbIX aTOMOB. Tlo3TOMy BOKpyT STOH OCH BO3MOXHO BpalieHHe OLHON Cpyriiibl ATOMOB OTHOCHTEAbHO Apyroii, O-CBA3b TIpH 3TOM He pa3pbiBaeTca. B pe3yibTaTe BpallleHHs yre- PouHad Lens MOXeT MpHHsTE CaMble paxIMyHble TeoMerpHyeckne (PopMbI: 3ursar, nozKoBa Ht sp. (puc. 6). [Ip stom He usMeHstomca HU OnuHe! Cex3ei, HU BANeKMHBIE yeNbi, T. e. HE COBEpLAaIOTCA NeiicTBHA, Tpe6youme 3HayHTeAbHO 3aTpaTbl 9Hepruu. MosTomy BpauienHe BOKPyYT O-CBASCHi MPOMCXOLHT JerKO; AIA Hero AOCTATOYHO Toi 3HEp- THM, KOTOpOii MoneKysbI OGNasaloT NpH OGbIYHOi TeMnepaType. Tipocmpancmeennwe opmei odnoii mosekyavt, obpasyromuecn np epawmenuu epynn amomos (@pazmenmos moaexyavi) eoKpy2 O-cen3zell, Ha- seieaiom Konopmayuamu (Konbopmepamu), a unozda — nosopomnemmu usomepamu. Takue cbopmbi MOueKysI HeycTOMYMBEI, OHH ObICTPO HK NOcTOAHHO MeHsloTes, Tlepexoa pyr B Apyra. J O6pamume exumanue: rp o6paz0BaKVuu KOHqpopMauMit XuMHye- CKOe CTpoeHHe MOsEKYbI (MOCIELOBATeEMBHOCTh CBASH ATOMOB) ocTaeTca HeM3MeHHBIM. Puc. 6, Mone HeKoropsix KoHcopMaliMt MoneKysnbI rleHTaHa Coctasnenve cTpykTypHbix @opmyn u3s0MepoB Z1a coctaBlleHHa CrpyKTyPHEIX (OpMys1 H3OMEPOB, PaaH4YalOLIMXcs 110- ‘CiELOBaTEMbHOCTHIO CBA3EIi ATOMOB YTsIepona B MOsIeKy.1e, HEOBXOAMMO: 1. Coctaputs crpyktypHyto (bopmysly yriepomHoro cKeneTa yrieBon0- Pola HOpMabHOzO cmpoeHuA C 3aaHHbIM YMCOM aTOMOB yriepona. 2. MocrenenHio ykopaunears uenb (Kaxapiii paz Ha ONMH ATOM yrnepo- 2a) H NpOU3BOAMT BCEBO3MOXHbIC NepeCTAHOBKH OAHOTO WIM HECKOSIb- KMX palHKasioB. 3 Mpumep. Cocraputs cbopmysibt Bcex H30MepoB yrleBoxopona cocTa- ba C,H, (reKcat!) 1 Ha3BaTb MX No CHCTeEMaTHYECKOH HOMEHKaType. 1. Coctasum (bopmysty yrieBonopona HOpMasibHOrO crpoeHus: (CH,;—CH,—CH,—CH,—CH,—CH, wereKca WIM reKcaHt 2. YKOpoTHM LeMb Ha OHH aTOM yrepona H OCyLeCTBAM BCEBO3MOx- Hble NepecraHoBKH patukasla —CH, Takum o6pa30M, YTOGbI HCKIOUNTS BOSMOXHOCTb NOYYEHHA HICHTHYHBIX COeIMHeHH (iA Gobel Ha- TAALHOCTH aTOMbI BOMOPOAa MOXHO ONYCTHTE): a, eke par de c-F-ee-c CH) CH—CHy-CH,—CH, € CH, \ 2-meTwanessTaxt ccc teed . 1 2 3 4 5 Cree eae CHC HCH Cis c CH, 3-mermanensTan 3. Ykopotwm yrnepozHyto LeMb ellie Ha O0MH ATOM yrviepona (BCero Ha Ba aroma C) v cile/laeM Bce BO3MOXHBIE NepecTaHOBKH JBYXx pallMkaslos —CH;: c—c—c-C , C4040—C—C-C 1 2 3 4 CH,;—CH~ CH-CH, cule HH, CH; 2,3-numeTun6yran \ t oe moe sos da ce ie CH;—CH,—C—CH, c | CH, 2,2-numerua6yTaH Alanbxeiiuiee ykopaunpative yrneponHoi uen HeEBOSMOXHO, KaK KH He1b3A BMCCTO AByX panHKasoB —CH, B3aTb omni —C,H.. Monymaiite nlowemy. TakHM 06pa30M, COCTaBNeHBI CTpyKTypHbIe (OpMysIEI BCEX H30- Mepos reKcaHa — HX NsiTb. 1 O6pamume enumanue: npoussonbHoe HCKpHBNIEHHe yrneBoOpoAHOH Wen He NpHBOANT K NOABIEHHWO HOBBIX H3OMepos. Tak, (POpMYJIBI CH;—CH,—CH,—CH,—CH,—CH,__ CH,;—CH, CH;-CH, CH=CH, COOTBETCTBYIOT OMHOMY 1 TOMY 2e COEMHEHKIO — FeKCaHy HOpMaJIbHOrO. crpoenna. °? Sananua 1. CocrapsTe MoneKyssipryto m cTpykTypHyto cbopmy.1bI ankatia, B MO- Jlekyie KOTOporo coxepxkaTcs 8 aTomoB yriepoa. Mpnpegute bopmysy roMolOra 3TOTO aiKaHa, MMEIOUETO Ha O/H aTOM yriepoyia MeHbue. Ha- 3OBHTe Be YIMeBOOposIEI. 2. Coctapste crpyktypribie bopmysibi: a) 2-meTwirekcaHa; B) 2,3,3-TpuMeTHsneHTana; 6) 3-MeTwarentana; 1) 2,2-numMerwanponana. YkaXUTE, KAKHE H3 YPIEBOAOPOOB ABIAIOTCA H30MepaMH. (@3. Uncno pemecrs, o603HayeHHbIX (popmysaMHu CH, CH,—CH,—CH,—CH,—CH, CH,;—C—CH, “cH; CH;—CH, CH;— CH CH,—CH,, CH, CH, CH,—CH, paBHO: a)2 6)3 s)l n4 4, Hasopure cnenyioulne yreBonoponbi 4 ykaxuTe dbopmMysIbI FOMONO- TOB H H30MepoB: 36 cH, a) cH,—o— CH; b) CH;—CH—CH, bn, CH, CH; CH, CH, 6) cH,—CH-cH, nD cHy—t— CH,—CH; on, 5. Coctapste crpyktypHbie cbopmysbr: a) 4-emop-6yTw1-3,5- Anmetusirentana; 6) 4-u30nponvi-3-sTunrenTaHa. 6. Ucnonbsys miacTwiM, H3roTOBbTe MOseM KOH(pOpMepoB oTaHa M GyraHa M HapHcyiite ux. OGbacHHTe HEBO3MOXHOCTE Cy- UWeCTBOBAHHA CTPyKTYPHbIX M3OMEPOB MH BO3MOXKHOCTH CyLLeCTBO- BaHs KOH(bopMepos 3TaHa. 7. W306pa3uTe Tp KOH¢popmepa rekcaHa. 8. Cpean dopmys, KoTOpbie npHBepeHbI HYKe (aTOMbI BOO- pona onyuenet sui Gonbiei HarnsgHocTH pucyrka), HaiiquTe HM BBITIMUIMTe CpOpMysIbI CTPyKTYpHEIX H3OMcpoB (Ha3OBHTe HX) H Konopmepos. JJonnuinTe ONYLICHHbIe aTOMbI BOLOpora. 5 c £ c c Cc oS NL cS eo coe e RG eg ¢ \, cc” Sc ae Xe ey ce Ce c—c—c 9. B coctaB yrnepogopoma KOAWYECTBOM BeeCTBa 4 MOJIb BXOLHT 1,2* 105 atomos yrepona H 2,88 - 105 aromos Bonopona. OnpeneazuTe Mo- JlekysspHywo (popmysy yrepozopona, COCTaBbTe CTpyKTypHyl0 cbopmyly ero H30Mepa, MMeIOUeTO YETBepTHYHEIHi aTOM yruepoma, M Ha30BHTE ero. © 10. Maccosas pons yrulepona B yrieBponopose cocrannaer 83,3%, or- HOCHTebHaA TWIOTHOCTS NapoB 3TOTO BelilecTBa NO BOMOpOy paBHa 36. MoviexyapHas cbopmysa yriesonopona a) C,Hy 6) CaHip B) CsHyp NGHp »

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