Onbra Bepezan = ueete) eae ha L=jFate) [olen a * pO3paxyHKoOBl 3aga4i Scions]: jie: Mi cie)siies-|-set- LT Kitac z a =| Pobounit SOWMUM-NOCIOHUK Cxpaneno Ana BMKOpCTaHHA 2 y 3aranbHOOCBITHIX HABYANbHMX Saknagax «__, ; TMOBTOPEHHA HAMBAKJIMBILUHX DMMTAHB KYPCY XIMIi 9 KJIACY Ypox Ne 1. Mosropenusa novarkoBux noHAT, po opraniuni pewonunn Opzaniuna ximin — ye posdin ximii, axuii eusuae cnonyku Kap6ony, ixnio Gydoay, exacmu- socmi ma nepemeopenna. Tepmix opeaniuna ximin me 1808 poxy 3anpononysas meencexnit ysennii 1. Bepueniyc. JJo usore pevoRmAn KnacudikyBaiH 3a TOXO/pKEHHAM, a ODKe pospi3HAIM pocauAHy, meapuHHy i “ixepanony xiniro. Tpurapaiimo ocHopui Binwinnocri Mik THNoBMMH OpranivauMn i TanoBHMH Heopranivnumu pevosunamn (ra6a. 1.1). Ta6auya 1.1. Bracmusocmi opeaniunux i neopeaniunux pexooun Tunosi neopranisni pesosunn Tunosi opraniaui peyosHAH Juia Oliwiiocti 3 HH xapaxtepHi Hion- xi (KCI, K,0) ta nonspui xopamenrni | mictars Kopancntsi sB's3KM 3n’s3Kn (HCI, H;0) MaIOTS MONeKY:NPHY (Oz, HCI) i Hemo- | maiors Hue MoneKyaapHy OyaoBy i MoneKynapHi sexynapuy (atomny, Hionny) 6yn0- kpucratiui rparku, a TOMy YacTO MalOTS Sarlax ay (SiO, Zn, NaCl . ‘C,H;OH, CH;COOH) 2 OF 3Ha4Ha YaCTHHAa PeYOBHH € esIeKTPoMi- ‘ , H,SO,, KOH, NaCl Ginsuticts € Heenextpoairamu (C)H;0H, CoH) Ginbuiers posumamomeca y BOM GimpusicTs He posnnmorees y nomi (CHy, CoHys GiaeuticTs — ne piawnn a60 TRepIi pevOBHHH 3 HH- 3bKUMH TeMnepatypamu tuiasaenns (CH;COOH, CH;OH) a GiubulicTs TopHT 3a TeMnepatypu, noHaa 500 °C, 6e3 nocTyny KUCHIO poskiayaiorEcs (CsHis) GinbuticTs € TReEPAHMH peyOBHHaMH 3 BHCOKMMM TeMneparypaMH TaaBieHAA Ginsmticts pesosnn € Heroprommnm Haiinpocrinsi 3 opranianux pevonun, Bix aKUX HOXonATe yci inuti — eyenesodni. Ix momexy- am mictaTs mame pa exementa — Kap6on i Tiaporex. Tomy icuye BusHa4eHHa: opeaniuna ximin —ye ximin eyenesodnie ma ixnix noxidnux. Byrnesogxi noginmors Ha nacuveni (axkanu) i nenacuveni (ra6n. 1.2). TaGauya 1.2. Dopuynu ma munu 36’a3kie y Monexynax deaKux eyenesoOuis Byrate- Soe - sommi | MOY: | crexrponni | erpykrypnt | _ Hanin- = aspui ps Li expystypui aT HH aa yei 38°s3KH Mix ao- CH. H-C-C-H | CH;-CH, | mawn Kap6ony onn- “aeni io at i HH we f-c-C-n MICTATS OHH NOspiii- CH, i CH=CH, | muti 38’a30 mixx ato- wenacu- el awn Kap6oxy enti Micra ommi mOTpili- Cath H-C=C-H | CH=CH _| nmi an’s20x mix aro- Mann KapOouy.Tipmranaiire susnaenua comoxoeiviozo prdy, comonozie, zomonoziunoi pisnuyi, Tipuranaitre opmyzy romonorisoro pazy ankanis. Hanmmits Ha3BM NepmmMx JecaTH Horo wWeHiB. Moxexysm opranisuux cnonyx, xpim avomis Kap6ony ii Tiaporeny, Moxyrs icturH ax inUMX exemenmis-opzanorenis (Oxcureny, Hirporeny, Cynmtpypy, Poctopy), Tax it aroun cux iHIMHX eeMeHTiB (Taz 1.3). Tabauyn 1.3. Moaexyripni ma naniecmpyxmypui bopmyau ocHoenux npedcmasnuxie pisnucx 6 ocuteno- i as opeaniunux cnoayk @yaxnionaaeni | vo oe cae f= ocopeeneehtaeais uni | eranon | GH,OH | CHy-CH-OH | omny abo xinoxa C3Hs03 CH,-CH-CH, | Timpoxenatbms rpyn | enon | C3Hs(OH)s on on OH |-OH oO Monexyaa MicTaTs Kap6onosi eTaHoBa, 4a 60 Katenora 02 CBC kapOoxcubuy rpyny Semmens ise alain arama P eapen emu foo re Dee sso | ee MoueKys1a MiCTHTB rinpoxcussi rpynm Monexyza Micrute Kap- Goxcumny —COOH ii aminorpyny -NH, Xapaxmepucmiuni (qbynxuiondavni) epynu— ye amon wu epyna amonis, wo symoexo- yom xapakmepui enacmusocmi opeaniunux cnoayk. Buxouaiime sasdanna 1, Hanmnivs kaniscrpykrypui dopmyan Gyrany, nesrany, retary, re O2. OGanenit» macy cymimi syrnesonnip, aKa MictHTL 0,75 moms erany, 5,61 ereny ra 1680 nx ermny (a. y). 3. Yeaxirs Macy riinepoy, ny; B) 7,2 r KapOony. T pp | I eres ehh lows aicae. + T { i i 4, Buxopucronyroan intepner-pecypen, nigroryiire nopixommenHa Mpo 3acTocysaHHa ByrCBOA- Hip (Metany, etany, eteny, eTHy), crmpris (MeTanomy, eraHomy. ritepomy), eTAHOBO! KACHO- TH, ByTIeBOiB i AHpiB. 5, Jo 300 r posumny 3 Maconoro yacrKo10 20% eranopoi KucnoTH noaamH 0,5 Monb dHCTO! eTa- Hosoi KucnoTH, OOuMcHiTh MacoRy ¥aCTKY KHCHOTH B OTPHMaHOMY po34HHi. Seaeni tal Peal Ped t ct t eo 6. Ins npurotysanis possnny BaKopuctana 2,2 Moms rainepony i 6,5 Moss BoaH. OOancmiTS wa ‘copy sactky (%) pewoBuHH B IpHroToRTeHOMy possHtti. all r ce ee fiz |A | Pee Eo oie i aus 53 i t “Macy posdHHy 3 MacoBolo YacTKoO 60 % etaHomy noTpi6Ho ZomHTH no 500 r ixuoro posuHAy “seeacono10 uacrkor0 10% eraxomy, 106 orpuMaTH posHHH 3 MacoBOIO HACTKOIO 20 % eTaHOmy? acy BosHOrO posHMHy 3 MacoBoI sacTKOIO 80 % eraxony ToTpI6HO zOmMTH 10 200 Mar ‘S0aH, 1106 orpHMatn posaHH 3 MacoBo10 4acTKOH 30 % etaHony? 06’em BomH noTpiGHO DommTH 10 200 r posHMHy 3 MacoBOrO YacTKOIO 8 % eTaHOBOi KH- ezoTH, 1106 smenmutu Macosy YacrKy KucHOTH 20 5%? TOBIJOMAeHHA mpo 306yTKH yKpaiHiChKMX XiMiKiB-opraHiKiB y po3BHTKy opra- ‘sisnoi xiii. Ypox Ne 2. Ximiani pnactusocti syrresoqHis Ta eranoBoi KUCAOTH. 3nauenns opranivnnx pesosnn ‘Tipuranaiimo sinomi vam ximivni snacrapocti syrmesomnis (aque. Ta6n. 2.1 i 2.2). L_ Yei syraesogui ropats (peakutia noBHoro oKHCHeHHa), yrBopioio4n Kap6on([V) oKcHy i Bony. TaGauua 2.1. Peaxyii nosnozo oxucnenna nacurenux i nenacuuenux eyenesodnie Tpynu Peakuia ropinna Byriepoanis (noBHOro oKHCHeHHA) | i amare eran CH, + 30, — 2CO, + 2H,0 ere 2C,H2 + 50; — 4CO, + 2H;0 erm T i HenacHueHi 2. Peaxuii samiyenna (nanpuknag, xnopyRaHia) npHTaManni ankanam, a peaxuii npuednan- (rasorenysanus, rigporenisaia) — HeHacH4eHHM ByrieBomHAM. TaGnuys 2.2. Peaxyii samiyenna i npucdnanna __Tpymu pyraesoauis ‘Xapaxrepai peaxuil cH.+ Ch ”S cHCl+ Hel nacuyenti samimenna iy CH, +2Cl, ——> CH,Cl, + 2HCI CoH, + Ha > CoH, CyHy + Ch > CoHsChe Ci, + Hz > C2Hy CyH2 + 2H2 > CoH, Henacu4eni MpHenHaHHA Baxmpum mpeqcrasnuKom oxcurevopMicHux opraHivHUx pe4oBHH € emanoea Kucnoma ‘CH.COOH. Y sonnnx posunax BoHa YacTKOBO AHCOMi0e, Ha BiAMinY Bia ByreBOAIB, CHupTIB | syraesogis, roGro € enexrpostirom, xoya i caaGKum: CH;COOH = CH;COO + H*Onxe, y Boquomy posunui etatonoi KucoTH aaKmyc i MeTHOBHi oparxesuit 3MiniOrOTS cpoc sa0apanenus. Matirxe sci comi eranonoi kucaoTH (emanodmu) A06pe pos4HHHi Y BOM, a TO- MY € CHIIBHMMH esiextposiramn: CHyCOOK = CH;COO” + K* (CH;COO);Ca = 2CH;COO" + Ca” Tipuragaiimo ximiuni Bractusocti eranonoi KucaoTH (Ta6a. 2.3). Tabnuys 2.3. Ximiuni enacmueocmi emanogol Kucnomt Pearye Pipnsnus peaxuii | 3 MeraiaMu 2CH,COOH + Mg — (CH;COO),Mg + Hat CH3COOH + KOH — CH;COOK + H;0 3 ayramn CH;,COOH + K* + OH’ — CH,;COO +K'+H,0 | CH,COOH + OH — CH,;COO +H;0 2CH;COOH + K,CO; — 2CHsCOOK + CO2t + H,O 2CH;COOH + 2K" + CO} — 2CH;COO + 2K" + CO;} + H;,0 2CH,;COOH + CO? — 2CH;COOK + CO,t + H,0 is coummn Buxonaiime sasdanna 1, OGuncnits Macy opranisHoro mponyKty peakuii xmopypanHa 33,6 1 Metany (H. y.) TaKHM ca- MuM 06’emom xsopy (ycHo). 2. Stxnit 06°em Kuomo (x. y.) Heo6xizunit Ut cnamozanns: a) 200 ma ereHty; 6) 0,8 w° erany (ycHo)? 3. OGuncnits kinpKicTs perosnH eTeHy, mo Mpopearye 3 14,2 r xnopy (ycHo). 4. Yuacnizox cnamosanus Meraxony yrsopwrocs 448 ma KapOon(IV) oxcmay (x. y.). xy Macy cnupry cram? 7 pennyDo 6r cymimi marnizo ii Mini aomum xocratio KinbkicTs eranonoi xncnoTH. Onepaxamt 1120 wan rasy (1. y.). OGsmenits Macony sacry (%) mini 8 cymimi eranin. Jas vosnoi Heitrpanisanii 250 r posunuy eranonol KucnoTH zogasn 0,4 Moms Harpili KapGo- nary. OGunczirs macozy uacrky (%) craHoxol KHCHOTH B HOUATKOBOMY posHHi. ‘10. Jonmmirs cxesm peaxuiti ta neperopirs ix ua ximiuni pisnanna: a) CH,COOH+ Na,O—-. 6) CH;COOH+ CaO 3) CH;COOH+ K,CO;— tT) CH,COOH+ Zn— Ti. Hasenins 78a nprxnagu pisnans peaxuili yrsopenna Kanbuili eranoaty. el Lt al epee —— errors ——- Sas 1 si 1 ba decd, i I ade haiti 4 a) 12*. Y 120r posumny 3 Macoporo yactKo1o 60 % eTaHonoi KHCHOTH MOMicTHAM MeBHy Macy Ha- ‘Tpiii kapOonaty. Onepxann 8,96 1 rasy (u. y.). O6sucaiTe Macosy yacTKy (%) eTaHoOBoi KH- CHOTH B OepkKaHOMy pos4HHi. 13*. Yuacuizox xuopyeanus na cairn 11 r ogoro 3 ankania onepaann 28,25 r auxnopoankany: a) yraHonits hopmyzy syrienogmo; 6) oOuncaiTs, aKuii 06°eM saline 22 r uboro anKany. TEMA I. TEOPIA BY JOBH OPFAHIYHHX CHOTYK Ypox Ne 3. Teopis 6yx0Bu opraniunnx cnozyK. BeranoBseHus MoseKky.1ipHoi ¢opMy.14 pewosuun 3a MacoBUMH YacTKaMH enemMeHTIB Ocuosni nonoswenna meopit 6ydoeu opzaniunux cnonyk Tporsrom. 1858-1861 pp susvauni ximixn-opranixu ©, Kexyse, A, Kynep, O. Bytaepos ‘HesaI€KHO OLMH BIJ OANOTO ONPHOAHHAM cCBOi Teopii, TKHMH HaMaramuca NoscHHTH XximidHy Gyzony opraniunux cnoayx. Ocnosni nonoxenna caoei Teopii O. Byrepos suronocus y 1861 p. sa 3'isai HiMeubkux npmporzogocnianuxis i aixapis. Bin suctynme 3 ZoroBigzmo «IIpo Teopito xi- sisnoi 6yz0B" i sanpontonysas yBecTH B xiMi1o Hone NOHATTA — «eTpyKTypa». Ocb ocHOBHI Ti0- aoxKeHHA uiei Teopii: 1, AToMM enemenTiB y Mouekysax OpranitHMx peioBHH cHory4eHi OHH 3 OAHHM y Te- Bui nocaigosuocti 3rimno 3 ixubow Banentuictio. Baxenruicrs Kap6ony 8 opranimux enonykax — IV. Tlocnidosnicmy cnoaywenna amomia y monexyni Hasueaiom ximiunow 6ydoeow (cmpyxmy- pot) Monexyau. Pistoeud ximivno’ @opmyau, wyo epadiuno eidoOpasicae posmauyeannn amonie inopadox 36’23kie y MoneKy.ti, nazuéaioms empykmypHoro. Ti pisnosnaom © naniecmpyxmypua @opuyna, y axiii 38°a3Ku Mix atomamn KapGony ti Tin- poreny He no3Hayeni, a cumpon atoma Pinporeny mumyrs Gina cmmpony atoma KapOony: H JH ¢ ene CH,=CH; H-C=C-H CH=CH ere ern Atomn Kap6ony MaloTb 3aTHicTh Clony4aTHcA OAMH 3 OMHHM, YTBOPIOOH TaHUKOrH pi3- nux Tunis (ra6x. 3.1).TaGnuys 3.1. Kap6onosi nanyoeu pisnux munie 2, Baacrusocri opranivnux pevoBHH 3anexath He amue Bin ix cKagy, ase ii Bix Gy;0- bu ixnix Moxexys. Tax, icnye Bi pissi pevoruen, xi Marors onMaKoBnii cxnax; ximintia (bopmyna KoxHO! 3 nx — ©,H;O. Ane cnonyks BinpisnmoTecs GyzoBo10 Monexy.t i, BianoBiHO, MaloTs pisni crpyK- Typui i waniacrpyxrypai dopmymu: CH;-CH;-OH CH;-O-CH; ceranon (pizmna) aumerimoauii erep (a3) tran: = 784°C tran: = -24,9 °C Haseaemo inmuii npuxnay: pesoumnn, aKi maoTs Momekyaspny dopmymy C:! CH;-COOH HCOO-CH; eraHora xucmoTa ean = 118,1°C Cnoayxu, Monexynu akux Maromb oduaxosy Monexynapny opmyay (Maioms odnaKoeutl xiC~ nuit i KitexicHuit cxrad), odnaK eidpisnsiomeca 6yOoso1 (cmpyxmypor) Monexya, nasueaiom Bomepamu. Aauye icnyeania maxux pevoeun nasueaioms izomepiero. 3. Y Moaekysax opranivnux cnosy« avon i rpynu aTomis BIAMBAIOTS OHH Ha O1HO- FO, HO BH3HAaYae BAACTHROCTI pedOBHH. Bemanosnenna monexyaapnot popmyau pevosunu sa macocumu wacmxanu enemenmie Moaexyaspua (ieramua) hopmy.ia oprarisnoi cnonyxu nae intbopmauito mpo: © acicrmit cxxay pevorusn (roGrTo npo enemexTH, axi € y cKsani ii MomteKys14); © xispkicuuii cktaq MonekyaH peyosunu (TOGTO cKimbKH aTOMiB KoxHOTO XiMiuHOrO eme- MeHTa MiCTHTS O2Ha MOsIeKys1a CHONyKH); © niqnommeHHa KinbKocTi aTOMiB KOKHOTO BuAY, MO € B MoneKyzi (a60 BiMHOMeHHa KinB- KocteH peyosnan exementis y cnonynt). Tax, is bopmyam masnexoi kucnoTH — C>H,O, — nizomo, mo: ‘© Mosexysia pesormun mictHt aromu KapGouy, Tinporerry it Oxcureny (axicnmii exam); * Mouexyaa MicrHTs Ba arom Kap6ony, aBa atom Finporeny 1a ¥orupu arom“ Oxcure- ny (KimbKicuuit cxnag); © siquomenus kimKocri atomis exementis y Monexyri N(C): NH): N(O)=2:2:4=1:1:2 © BiTHOMeHHA KiMbKOCTE! peyORMHM eveMeHTIB y CNOYHi n(C): n(H) : n(O)=2:2:4=1:1 3abaaKH BINHOMIeHMO MoxHa BCTAHOBHTH Haiinpocmiury dbopmyzy, To6TO Taky Mopmyzy, ¥ axili inmexcn € Haiimemmmn 3 ycix MoamBnx. Tyr — CHO}. Aux oprasivaux pesosm, ictanni dopmyinm xxux C3Hy, CyHg, CsHio, naiinpoctimow € dopmyna CH; ockimkn: 101)N@:N(H)=2: 2) N(C): N(H) =4 3) N(C): N(H)=5:1 Posp’smyroun sanaui Ha BeTaHoBNeHHA hopMyan, cHowaTKY BCTaHOBMOITS Haiinpocrimy Gopmyny. Axwo Bona 6iraetsca 3 icruHHOW MOneKysapHO! opMyzor0, To B yMoBi 3anaui He- sae nonatKonoi inopmanii, ska Zana 6 sMory OSuNCHHTH MOnSpHY 4H BiMHOCHY MomeKynapHy macy. Slamo x ictHHHa Momexysapxa popmyza BippisHaersca Big Haimpoctimoi, 10 B yMoBi 3a- aaui 0608"a3K0BO Gysle BKAIAHO O”MH i3 NapamerpiR: © rycrmua rasy; © rycruma rasy (a6o sumapis pinkoi pevosun) 3a BomHeM, TOBiTpsM, inMIMM rasom; © Maca mesHoro 06’emy rasy. 3anaya 1. Haiimpoctima dopmysa syrnesozmo CH, a ryeruaa sunapie nici pevosunn 3a somueM cranoBurs 42. Ycranonirs Monexys1apHy (icrHHHy) bopmyay ByrICBOTHIO. Haxo: Pose’xsanna Haiinpocrima dbopwrysta — CH MC Hy) DufCH,) = 42 1. Buxopuicrasunm opuryary Dyz(CxHy) = 7T->— » O68He- GHy—? JOEMO MONAPHY Macy ByTIEBOAHIO: M(C,H,) = Dy,(CxHy) + M(H) = 42 + 2 = 84 (r/mome) 2. OSanemoemo, y cKinbKH pain MonspHa Maca ByreBogto (84 r/Moms) € GisbuIOIO 3a MO- aspxy macy rpyrm aromis CH;, M(CH2) = 14 r/monp: M(CHy) _ 84 r/wome _ (CH) ~ 147/Mom Monexyssapua dopmysia syrnesoniio — CsHy2. Bignosign: CoH. 3agaua 2. Ycranosirs MonexyrspHy opmymy ByrmeBoqHi0, Macona yactka KapOony B axomy cTaHoBHTs 83,33 %. Flan Po3e’azanua C) = 83,33 % 1, OSunemwemo Macosy 4actky I'igporeny 8 cromyui: A, —? w(H) = 100 — 83,33 = 16,67 (%) 2.Tipanycramo, mo Maca syraesoamo cranosuTs 1001. Bukopucrapmm dopmyay m(C) w(C)= (C,H) , BH3HayaeMo: m(C) = w(C) + m(C,H,) = 0, 8333 « 100 = 83,33 (0). Toni: m(H) = 100 ~ 83,33 = 76,67 (r) 3. OGuncmoemo Kinsxocti pevosnun KapGony ii Pigporeny p mit pesonnni: c n(Q)= eye = BS - 6.94 (om) m(Ht n(H) = AED = 165-1667 (wom) 4, Tou nusnasenna inzexcin y Moxexyzspniit (bopmyni— a ue Maors Gyr nimi esa — samcyemo BisHomenta KimbKocTeli pewoBMH enemenTi n(C) : n(H) = 6,94 : 16,67 22,4=5:12. Bianosias: Monexynspua bopmy.1a Byrssesoamne — CsHy2.Sagaua 3. Ycranonirs (bopmyny opranivnoi pesoanuu, Macosi yacTKH KapGony, Tiaporesy ta Xnopy 8 sxili, ninnoniano, cranosnats 24,24, 4,041 71,72 %. Fycrana sunapin wiet peroommn 3a BoaHEM — 49,5, Jano: w(C) = 24,24 % 04 % w(Cl) = 71,72 % Dy,(C.H,Cl,) = 49,5 Poxe’asannn 1. Hpunyeramo, mo € 100 C.HyCl,. Toni: m(C) = 100 - 0,2424 = 24,24 (r) m(H) = 100 + 0,0404 = 4,04 (r) m(Cl) = 100 - 0,7172 = 71,72 (r) CHCl, —? 2. O6snemoemo KimekocTi peYosuNM KOxHOTO esTeMeHTA: m(C) 24,24 MO) Ga(Gy = AE = 202 (som) mH) 4,04 mH) = aay = yp = 4.04 (wom) mC) 71,72 n(Cl) = M(Cl) ~ 3557202 (om) 3. Sanucyemo Bignomenus KinsKocreii perouma enemextis: n(C) : n(H) : n(Cl) = 2,02 : 4,04 : 2,02 Haiinpoctima @opmyna — CHCl. 4. O6ancmoemo Mossapry Macy oprawisHoi pesosunn: M(C,H,Cl,) = Dy,(C,H,Cl,) + M(H) = 49,5 + 2 = 99 (r/moas). 5. Mopisinoemo monapry macy Hesixomoi cnonykH (M(C,H,Cl,) = 99 r/woms) i momspay Macy, oOsHcaeHy 3 Haiinpocrimoi dbopmy: (M(CH2Cl) = 49,5 r/moz): MICH Clade sg. far MCHC) = 49,5 Tajekcu 8 Halinpoctimii dbopmyni caiq nOMAO:xKHTH Ha HBA. Binnosia: ictunna hopmyna perosnan — C,H,Cl>. 3agaya 4. Yoranonirs hopmyay rasysaroro Byrnepommio, Macosa yacrka KapOony B aKOMY cranosuTt 88,89 %, a rycrHHa crionyku 3a HOpMamEHAX ymon — 2,41 r/n, Alan: Po3e’asanna w(C) = 88,89 % 1, Tpunyexaemo, mo pevosurm C,H, € 100 r. Toni: m(C) = 100 - 0,8889 = 88,89 (r) m(H) = 100 ~ 88,89 = 11,11 (r) 2. Obancaioemo xixbKocri pesornan KapOony ii Tinporeny 8 erromyui: = m(C) ~ 88,89 2 n(C) Fey Tan 7 741 om) ny = 2) = ML = 43,11 (vom) M(H) 1 3. Sanneyemo signomenna kitsKocreli pevosun Kap6ony ii Tinporeny. nC): nH) = 7,41: 11,11 =1:1,5=2:3 Onxe, naiinpocrima bopmysa cnoayxu — CoH). 4, na oGunenena MonapHoi acu, 110 siztioBizae Monexynapuiti hopmysti cnonykH, BEKO Puctonyemo dopmysy M(CxHy) = p(C,Hy) « Vy (Vue = 22,4 w/Mons): M(C,H,) = 2,41 + 22,4 = 54 (r/wozs) 125, OGunemoemo Mouspuy Macy, mo Bixnoninac ualinpocrimtiit bopmyai CyHs: M(CoH3) = 12» 2 +3 = 27 (r/wom) 6. Hlopismoemo Monsapry Macy HeBixomoi cnonyxu (M(C,H,) = 54 rimomp) i moaspry Macy, ‘eSsncaery 3 naiimpoctimoi bopmyn (M(C2H,) = 27 r/momp): 54:27=2 Tlomuoxxusiun ingexcu naiinpoctimoi opmyan Ha 18a, OTpHMyeMO MoueKysapHy dopmyny pesosman — C,H,. Bignonigan: monexynxpua dopmyna perosuan — C\Ho. Buxonatime sasdanna L Tlopisisiire rimoxicnnit ra axicrnit cxnan i Gynony MoseKya ereny it exmy (ycuo). 2. O6uncaits Monapry macy 6yrany 7a foro rycTuHy 3a HOpMaNBHMX yMoB. a ea T Pepe pry Pepe set j | +. 4 | | Bt 1 | | | Ce eee ee : 3. Hanuurirs mosexysspyy i crpyxtypay dopmyaam eranomy ta oGancairs Macopy sacrky OxcH- Tewy 8 cupti. 4 a ope | sbeotaetsctestest 1 LTT Ue ces ok aad 4 3 posrailyxXeHHM KapOOHOBHM JaHIVOTOM J14 peyoBHH, Sa ; ~ o end joa pce i Piseritt ime 5, OGanenirs renew. ¥ Fee ory palhs peeet este | it te tet | sos | | ene y } Tre tre i j Bei ells L eet, L Ls CH, 5 a) CH-CH- wets i i ace CH, 6) CH,-CH-CH-CH: HCE i -CH-CH: OH OH OH OH be HOH OH Bianosigp noscnit (ycxo). 7. Haseaits popmy.m BinoMHXx BaM ByrneBOmHiB, mKi He MaloTS i30MepiB (ycHO). 138*. KapOou(IV) oxcwn, onepxxantii yuacninox cnamosanns wnkcroGyrany one mponycTa- CH, AM Kpi3b pO34HH, IO MicTHTS HazMUIOK Kaniii rigpoKxcuay. Ha Bsaemosiro 3 Onep»aHOH cin- mo BurpaTH 50T pos¥HHy 3 MacoBo1o YacTKoo 30% eraHonoi KucHOTH. Sky Macy muxno6yrany cham? 9. Bukopucrosyroun intepHeT-pecypcn, niqroryiire nosixomaenna nmpo 3navenua Teopii ximivnoi 6ydoeu opeaniunux cnonyK. Ypox Ne 4. Ipakraune 3ansatTs. Beranopsenna MOJIeKY1ApHOi OpMy.IH pe4OBHHH 3a MACOBAMH 4acTKaMH esleMeHTiB Posrnaemo we ofHy sanayy. Y wil 119 BcraHoBmeHHA MoueKysspHoi opMysm pexoBHHH nnkopuctonyerees inpopmania mpo 06’eM nennoi MacH ByrneBomM0. 3agaua. Yctanosits cbopmyay rasysaroro ByrneBomHio, Macosa 4actka Timporery B aKOMy cranosuTs 14,29 %. Bigomo, mo 168 r fioro 3aiimae 06’ 67,2 31 (#. y.) Tax Po36’azanna w(H) = 14,29 % m(C.H,) = 168 ‘C,H,) = 67,2. GA, T cnoci6 1. Tipnnycrazmn, mo € 100 r cnonyku C,Hy, o6uncmoemo: m(H) = 100 + 0,1429 = 14,29 (r) m(C) = 100 - 14,29 = 85,71 (0) 2. O6ancmoemo ximbKocri pesonu KapOony ii Tiaporeny: _ mC) _ 85,71 _ n(O)= ™M(c)~ “Tp = Tl4 (tome) _ (A) _ 14,29 _ mH) = Figay 7 7 1429 (won) 3. 3amvcyemo BiqHoMIeHHa KimbKocTeii perosuH KapOony ii Tigporery i mpuBogumo Horo 10 uismax uuces: n(C) : n(H) = 7,14 : 14,29= 1: 2. Haiinpocrima dopmyna cnonyxu — CH). 4, [Ina o6anicnenua MonspHoi Macu cnonykH B ymosi 2aqa4i ¢ zaHi mpo o6’eM TeBHO! MacH ByrieBoaHio. OOancm0eMo KinbKicT PeYOBHHH BYTNCBONHIO: VC.Hy) 67,2 (GH) = Se =3 (wom) 5 Se 2 an aca 1 opaym m(CaH) = cay napry macy C,H: m(C,Hy) M(C,Hy) = TCH) i = 56 (r/momp) 6. OG4nemoemo, y ckimKH pasin MoaspHa Maca (icrHHHa, 56 r/Moms) € GinBMIOIO 3a MomAp- uy Macy CH; (14 r/moap): 36 = 14 7.Tlomuoxusum ingexcu nalinpocrimot opmysu Wa yorHpH, OTPHMyeMo MosIeKynApHy opmyny peroBuun — C4Hs. Tl enoci6é 1, [laa oO4ncaenHa MonapHoi Mach cnonykH B yMoBi 3aqa4i € Jani Mpo 06’em neBHOI MacH BYTNeBOAHIO. OGUHCIOEMO KLIBKICTS PeYOBMHH BYTEBOHIO: 14V(C.Hy) _ 67,2 A(C,H,) = —2 = S12 = 3 Quons) (C.Hy) Tar a Tt m(C,Hy ) 2. Ib dopmym (CH) = 37 (GH, y oSwHeatoeo Monspury Macy CyH;: mCeHy) 16g MICAH) = GH) = “5 = 56 lon) 3. O6unemoemo macosy yactky Kap6ony y cnonyni: w(C) = 100 — w(H) = 100 — 14,29 = 85,71 (%) Ay (C)* NI 4. 3a opmystoi0 w(C) = oe o6aucmoeno Kinbkicrs aromin Kap6ony 8 Monexysi BYrmeBOnHW: _ M(C,Hy)xW(C) _ 0,8571x56 _ a 4© BT <= Ar (A) * NA) sehen aches 5. Ananoriuno 3a bopmyato10 w(H) = “M(CH,) oOunemoemo KimbKicts atomis Tigpo- y TeHy B Mouekyni ByreBOHIO: M(CyHy)xw(H) _ 0,1429x56 Ne) = eae a te 4-(H) 1 Bianopige: ictauua dbopmyaa perosann — C,H. Buxonaiime sasdanna 1, Haiinpoctima dopmyaia pesosnun CH, a monapHa maca — 78 r/moms. Yeranonits wonexynap- Hy opmysy pevosnnu (ycHo). 2, HaiineSesneanimun sa0pyarionayamn nopKizaa € xnopoopranini cromyku. Cepen HAX € Ta- xi, mo Mictars 14 atomis Kap6ony: CyyHoCls, CysHsCla, CraHioCls. Mopisusiire ui pesos sa sxicnum i xinexicnim cenayom. Y axiii 3 Hux Macona vactka Xnopy HaliGinsuza? Un Tpariaore- ca cepem Hux Taxi, naiinpoctinti hopmysn aKHx € onHaKOBHMH? (YeHO). 3. Yeranonirs Monexyaapny @opmysy rasyBaroro ByruieBomHio, FyCTHHa #KOTO 3a HOPMAmbHHX yon cranosntt 1,964 r/n. T pera ayy i Jas 1Sere ee | t i 3. Tyermia simapis pesosmi 3a sommem craonnrs 45. Macosi Oxenreny y cnoayni, niqnonigao, cranopasts 0,2667, 0,0224 i 0,7109. Yeranosirs momexy- aapny bopwysty croaysn. e TTT TI [at | ae r so ! 7*, Maconi actkn KapGouy ii Oxcureny Sauna choayui, BumoniqHo, cranopnaTe 55,81 i 37,21 %. Tycruna sunapis peyosmi 3a nome craHonurs 43, Ycranosits MoneKyaapay ¢op- Mysly cHoayKn. 8*. Yeranonins dopmyny oxcurenosMicuoi opraniuuoi cnonyKu, aKa yrBopIocTscs Nii, Yac KRAIICHER xanycrn. Macosi wactxu KapGouy ii Piaporeny y cnoayui, simoninno, craronnsts 40 i 6,67 % Monapaa waca pesosunt» 1,5 pany Oimsura 3a Monspay macy craonoi xucroTH. 9*, Monapua Maca omniei 3 opranisaux xcaor y mats pasis Ginsiia, nix MonspHa Maca erasly, Haiinpocrima hopmyna pexonnan C)H;03. Yetanonits moxexyaspry dopmysry pewonnan. Tecmoei 3aedanna 1. Hatimpoctimy dbopwryy CH; mae Gararo opraniummx pesosma. Yeaoxirs (bopmymn TaKHx cnonyK: 1) CsHy; 2) Cag; 3) CrHa; 4) CoH; 5) CoH 25 6) CoH A1,2,3 B 2,45 B 4,5,6 T 1,3,6 Anco 2. Vann napy pesonun, natimpocrimi bopmysn aKHX € onHaKkoRAMH: A CsHs i CigH29 B GyHe i CsHe ABBLC B C.H,O, i CH,O T C,He02 i CsH,O O00 163. Yeaxirs Monexynspay hopysly rasysaroro Byrnewosio, rycTHHa aKOTO 3a BoAHEM craHoBUT 15 A GH, B GH B GH, r CH, Aba 4. Yeaxirs cymapny Kimbkictb aromis y MoueKyni crloxyKH, Haiimpoctima dopmyna akoi CH;0, a rycTHHa BrmapiB 3a BOAHEM CTaHOBHTS 31 AS B8 BO T 10 S.Ywxirs hopmyny oxcurenosmicuoi oprasinot perosmiim, rycraxa sunapis 3a restien Koi cTaHOBHTE 8 A C3H,02 B C,H,O B CH;0 T CH,O Ypox Ne 5. Xapaxrep ximivnnx 3B’ s3KiB y MOJeKyAax OpranidHHx cnomyK Atom Kap6oxy B cnosykax yrsopioe JMIe KOBANCHTHI 3B°a3KH. 3aBaxKH 3naTHOCTI aTOMiB Kap6ony cnonyyatucs o2HH 3 ODHHM ii yrBoproBaTH KapOonosi zanyiozu icHye Tye BeNMKA KiTb- ict opranivnux pevosuHax. PosrisHbMo pi3Hi BHNAIKH yTBOpeHHA KapOou-KapOOHOBHX 3B’s3KiB. 1, Ipoctnii 38’s30K Ximiunuii 36’930K Mio d60aa amomamu, wo ymeopioemeca oduicio cniteno1w napoio enexm- pouié, nazueaiomb npocmum (odunapnum, opdunapnum). Y monexyzi Merany CH, € ornpn npocri 3n’s3KH. ¥ Monexyzi erany CH, ¢ cim mpocrax 35°93KiB, ONHH 3 HAX — Kap6oH-KapGouoBnil: x i HH I1-C-CH H HH HCH H H 2, Monpiiinnii 38’s30K Ximiunuii 36’230K ioe 060ma amomamu, ymeopenuit 3a donomozow deox cninenux exeKm- pouuux nap, Hazusaiom» nodeilinum. Yrsopenus monexynu eteny C,H, Moxna posrmainytn sk pe3ymbTaT BimmeMeHHA ABOx atomis Tigporeny nig pisnmx atomis KapSony B Momexysi erany. Mix atomamu KapSony yrBo- pHOcTECs MomBiiiHMii 3B’ n30K: HOCH HH 3. Horpiiinnii 3n’n30% Ximiunuii 36’a30x sine O6oma amomamu, ymeopenuti 3a donomozo!w mpsox cnineHux enex- mpounux nap, Hasueaiome nompilinum. Yreopenua monexysm eruny C,H, MoxkHa posraaHyTH aK pesysbTaT BiNMeMeHHA DBOX eromis Tigporeny sig pisuux atomis Kap6ouy B Monexymi erany. Mix aromamu Kap6ony yTBo- pioersca norpiiinuii 3B’930K: Tlodeitinuit i nompiiinuit s6'asxu Hasusaioms Kpamnunu. Xapaxmepucmuxu Kosanenmnux 36’asxie 6 opzaniunux cnonykax 1. Kpamnicme 36’a3xy euznavae xineKicme cniaenux enexmponnux nap, aKi 36’azyiome amonu. Binosizuo, Kowatenrunit s8’x30K Gysae npoctam (oAMHapHEM), HoaBiltHAM i norpili- sux, [logpiitni Ta norpiiini 38’a3KH yTBOpIOITECA, AKIO aTOMH YIBOPIOIOTS OHA omy cnimbny mapy enekrpouis; ix We Ha3HBaIOTb KpamHwMU, a MOIIEKYJIM 3 TAKHMH 3B’ s3KAMH — HeHacuyeHUMU, 2. Alossicuna 36 "a3sKy — ye sidcmanb amione yenmpamu dep amomié, Axi yméoprowme 22 '330%. li susipiowors y Hanomerpax (1 HM = 10° m). Ha nomxnny 3n’saxy ictorHo BrulMBae Kpa~ THICTS 3B’A3Ky: MO BHIa KpaTHiCTs 3B’x3Ky, TO MeHUa Horo 1oBxKHHA. 3i 36imbMIeHHAM pastiycin STOMiB, Mix sKHMH BHHMKa€ 3B°930K, 30L1BINYETECA i loro AOwKHHA. 17 “2 Bepesan O. Xintis. Soumr-nociGuux. 10 xx.3. Enepein 20’ asky — ye enepein, axy nompi6uo sumpamumu, 406 spyiinysamu 36'a20K, a60 enepein, aka eudimemeca nid vac ymeopenna 2e‘asky. li smipwowre y KinompKoysax Ha Moa (KJbx/moms). Ha eneprito 35’a3xy icTOTHo BrLinBac KpaTHicte: 110 BHIIa KpaTHicTS 38”x3Ky, TO Ginswa Horo enepria (stinnicrs). 3i 36immenniaM Minnocri 32’ssKy Horo oHKUHA SMeHUIYETSCA. Buxonaiime sasdanna 1. O6suonits rycruuy Byrsenopmio 3a BOAHEM, y cKAaLi MoneKysH sKOrO € TpH atomH KapOony. Monexysia micrurre onus norpitinuait 38°30. [ected a als 4 3. ¥ exami opranissol crionyxu © arowu Kap6ouy, Pinporeny Hi Oxcureny, maconi sacran skux cranosasrs, Bignosinio, 39,13, 8,7 1 52,17 %. Biuioca MomexynapHa Maca pevosuHH BaBiai eTanoay. ¥eranosire nonexyypay dopmyy pesos ee at Hi 4. Yeaokire saranbuy KuILKict» upoctux i nogpilitmx 3B's3KiB y cHlomyni, W yaa axoi CH,-CH-CH=CH-CH, (ycuo). CH=CH, 5. Yeoxite saranbuy Kinbxicrs KOBANeHTHUX 38"a3KiB y cHOnyui, HamiBcTpyKTypHa hopmysia aKoi ¢-CH, > CH-CH=CH, (CHO) cH, I, (ycuo). 6*, Yeranosirs Monexyaapuy hopmyay ByrsieKosHi0, MoxspHia Maca sKOrO CTaxOBHTS 56 T/Moxs, a Monexysia MicTHTL OaMH NoZBiitHHit 3B°s30K. 7*, Yorantonirs monexyaapry opMy:ly rasysaToro ByrsieBomHo, MacoBa YacTKa atoMin KapGoHy B aKoMY craHoBHTs 82,76 %, a 11,6 r foro 3a 1. y. salimae 06'eM 4,48 1, OGuncains rycruny WbOTO BYTIEBOTHIO 3a remieM. 18Tecmosi sasdanna 1. Yeaxite dopmyny pesooman, aKa MictrTs i nonpitinHi, i norpitinit 38’s30K. A CH;-C=C-CH;-CH; B H-C=C-CH=CH ABBY B CH;-CH=CH-CH=CH, I’ CH;-CH;,-CH=CH, 2. Yeaxite bopmysy peyonen, y aKili yci 3B’a3KH npocti A CH)=CH-CH=CH; B CH=C-CH; CH, CH, CH, B CH,-CH-CH-CH, T CHy-C=C-CH, CH; 3. Sixi Tana 5p’ askin icnyrore y cnomyni, naninerpyxrypua dopmy:a sxol CH;=CH-CH— CH, ? CH,-CH, A onmuapni B noni B ogunapui ta norpilinuit T ogueapsi va nozpiiinnit 4. Yaxirs saranny Kinskicts ommnapaux i noxsiiiaMx 3B’a3Kip y cnomyni, HamiscrpyxtypHa hopmyna axoi CH,-CH-CH-CH, CH, CH, A 18 B19 B 20 r2i 5. Yxaxits KimbKicTs KpaTHEX 38's3KiB y cnomyui, HaniserpyKtypHa dpopmyzia KOI CH,=CH-CH=CH-C=CH A2 B3 B4 F-9 Ypox N 6. Knacnixania opraniunux cnonyK Knacuixauin dynxuionansuux noxidnux eyenesodnie Opraniuni peyosann pospisnaioTs 3a HasBHicrio neBANx xapaxmepucmusnux (bynxyiona- ‘abnux) epyn, ix Kimbxicrio i posramysannam. Xapaxmepucmuunorw (dynxuionansnow) zpynow Hazucaome odux amom abo cyKynuicms amonis, wo 3ymoauoe xapaxmepni ximivni enacmusocmi Knacy opeani4unux cnoayK. Vueni pospisnmors ronan 100 yaxnionamsaux rpyn (HB. Ta6x. 6.1). TaGauys 6.1. Xapaxmepucmuuni epynu pisnux Kaacie opeaniunux pewosun Xapaxrepuermana rpyna Kaac opraniuuax cnonye hopmyaia wa3zpa garaabua @opmyaa Haspa -F,-Cl, bayopo-, xs10po-, R-Hal rajloreHoankann -Br, -1 Gpomo-, iion0- Ar-Hal ranorenoapen: } R-OH chupm —OH riagpokcmibna ArOH enom, aco R oe? ; alt) —( Sa nerigaa Sy ampqeriga ace? 601 Rc? GoHOB: SOH KapOoxcw1bHa “OH kap6oxosi KHcHOTH O 0 a oA R-C coe ecrepna So ti ectepu —-NH; aminorpyma R-NH);, Ar-NH> aminTonye Gararo pesonun, Monexysn axux Mictars Ginsne, Hix omy bynKnionansny rpyny; HasHBAWOTS zemepopynxyionansnumu, Jo HHX, HanpUKIaZ, HanexHTS Knac GidyyaKyionam cilonyk — aminioKHcsoT, aKi MictaTs amino--NH) i kap6oxcussny rpyny -COOH: NH;-CH;-COOH B ocuosy kxacupixanii syrnenoanis noxiayeno THI 38’s3KiB Mix aTomamn Kap6ony i aosy kapGoHoBoro JaHuora. Aumecainni nyrenoani Uuxctisuti syrnesoani apomaratni animist (apexn) | aaKeH : CH,-CH-CH,-CH, newacuueni CH-CH, akin HacHeHi CH-CH, CH=C-CH,-CH, (wenoanxann) ?. Sarai HCH, ‘CH,=CH-CH=CH, CH,-CH, Buxonatime sasdanna z S-on A “OH 0. . JIumonny Kucsoty Hoo CH C-CH-C. is coky wecTuraux mmMonis 1784p. suainue OH uipeqcekuii xiMix-cbapManest Kapn [[eene. Cxnazits monexyaspry opmyzy KHcnoTH, onn- nite ii axicunii 1a kinsxicuuli cag, Hassire bynxuionansui rpynm, wo mictute ii MomeKys1a, yaxirs ix eee CI pS PoE SBSEe uHCHITE, eb Aftab pease. espera etry fr Sree eo | 3. ¥ cusani monexyam nitporenosicuoi opraiswoi cnonyxa € aromu Kap6ouy, Fixporeny i Hi- tporeny, Maconi yactkn aKHx, niqnonimHo, cratoanaTs 55,81, 11,63 i 32,56 %. Tyermna suna- pis pedonuan 3a nonirpsm cranosHrs 2,966. YcraHonie bopmyny pexonuin, 20cole slasher Kalil bl chi bodied wscler) 5. Tlix vac irrrencusxot diswanoi po6or y M’asax HeTpenosaviol m0/IMHM HaKORYyeTseR MomO“HA HH Tpynu Mictuts ii Momexyna? Yn Moxa 3apaxyparu ff 10 Gidbyrxuionamumx cromyK? (YcHo). 6*. Ximivnnii ckaaq BHHHO! KUCHOTH MoxHa ONHCaTH 3arabHOIO bopmyno10 CyH,Og+2. Monsapua Maca KHCHOTH cTaHOBHTS 148 r/mom, Yerawonit» ii Monexyaapxy dbopmyzy. ° xucqoTa CHy-GH-C » ka 3yMoBMmoe cheudi4Hnit M’s30Bni Gimp. Sixi xapaxrepuctaanti OH Tecmosi sasdanna 1. Yeaxirs bopmyny au6pomonoxinuoi nponany ACHB: = BGHyBn BOHBn —T GHsBr Aeac 2. Yeaxits hopmyny oKcHreHoRMicHoi opraniynoi cTOyKH A C3HsCl; B CjH,0, B C.H,N T CeHiz 3. Yeamirs kapGoxcwsny xaparrepucrusny rpyny A -OH B -NH, B -CHO T -Coou 4. Yeaoxins nanivctpyerypay dbopmyay newacuyenoro ayrnenonmio ; A CH;-CH-CH, 5 H,C-CH, B Ga T CH,-C-CH, A cH, CH, CH, b 5. Yxaxire nanisetpyxtypay opmyay empty y 50H, CHy ABBr A CH,-CH,-C% B CH; oe oooo B CH,-CH-On BE el CH, CH,-CH,Ypox Ne 7, Mousarrsa npo ssuine isomepii Ta isomepu Tromepu — ye peroeunu, xi maiome oduaxosuil axicnuit i kinoxicnuil cxrad, ane pisny ay monexya. Aeutye icnyeanun ixomepnux cnoayK nazueaiome Bomepic. Sisnme isomepii iaxpus ©. JTiGix (1823 p.), a nasny aan Lf. Bepneaiyc (1830 p.). Biaomo smxa Buia isomepii, axe Haiipaxctmpimo%o cepen HX ¢ cmpykmypHa. Tsomepivo, 3ymoaneny pizno1 nocnidoenicmio cnomywenna amomis y MoneKyAax, a maxonie uM poaMiuenHaM Kpamnux 36'A3Ki8 y Hux 4M NeeHUx zpyn amomis, HasUBaIOMe CmpyKmypHor. Crpyxrypua isomepia moxe 6yrut symosniena: © pistow nocnigosuicno cnonysexna aromis Kap6ony a inmux atomin y MomeKymax: TEE erty © pisun posramypannam xpaTHHx aB’askiB y crpyktypi MoxeKysl, Hampuxnaa: CH,=CH-CH;-CH; — CH;-CH=CH-CH; © pisnie posramysannam gymenionamsnnx rpyn (Hanpmorat, ana crupry C3H,OH ami Ba BHNAAKH 718 posMimentia riapoxcHbHoi rpynH): OH 2 CHy-CH-CH,-OH — CjH;OH + CH;-CH-CH, © nanexsicnio crionyK no pisHax Knacis (atisexnacosa isomepia, fi posraanarore aK mani pw erpyktypHoi isomepii). H,C—CH, CH,=CH-CH;-CH, — CiHs > a “le o 2 CH.-CH-C. | CHO > CHC ps Ae eee \O-CH, 3i s6inbmrenuam kinbkocri aromis Kap6ouy » monexyni opraniunoi cnomyKu cTpiMKo 361m yetscs i kimexicts isomepis: 6yran CyHy mae 2 isomepu, nentan CsH,2 — 3, rexcan CoHig — rena C7Hyg— 9, oxran CsHjs — 18, aexan CioHo — 75 izomepis. Yucno isomepis ne Hy C\sHy) cranonure 4347, tpuxontany CyyHo — 4111 846 763, a Terpaxorran CiHp HeiiMosipue Hc10 izomepis — 62 491 178 805 831. Bukonaitme 3asdanna 1, Posrnanpre Hanisctpyktypni bopmynn TpEox pevoBHH H,C-CH-CH, Hin Ge CH, H,C—CH, ‘Un Moxua ix nasparn isomepamn? Binosins noscuirs ycxo. 2. Onmmirs kinexicnnt i axiceii cknan peiosun, uanisetpyktypHi cbopmymn aKux: CH)=CH-CH,-CH, pl BL atk CH;-CH=CH-CH,-CH; CH,-CH-CH-CH, H,C—-CH, CH, ‘Un moka ix Ha3BaTu isomepaMH? 3. Yeaxxits, aki 3 peqosuH, @opMy:H AKUX TomaHi HMKe, € is0MepaMH (yCHO): a) CH,=CH-CH,-OH 6) CH,-CH-CH-CH, OH marae 1) CH.=C-CH,-OH H,C—CH, cH, 224. PosrnaHbte HaniscrpyktypHi (bopmyan OpranivHux peyosun. Tn € cepen Hux isomepu? Bigno- pine o6rpynyiire. Vxaxxirs ix: OH a) CH;-CH,-CH;-CH;-OH 6 CH-C-CH, cH, 3) CH;-CH,-O-CH, 1) CHy-CH,-O-CH;-CH oo e) CH,-CH-CH-CH, H,C—CH, OH OH ve 5. Yate fsomepamn cnoay, opmyine saan: CH CH,~CH,~CH, i CH»=CH-CH,-CH,-CH,-CH? cH, Biqnosigs noscuirs ycuo. 6. Yeaxins, aKi3 pevosun, hopmyan aKnx nozani MmKe, € fzomepamn (ycHO): 5 1 a) CH,-C-CH,-CH, 6) CH,-CH-CH-CH, 8) CH,-CHy cH, H.C CH, cH, CH, Cl calcu, Ae 1) CH,-CH,-CH-CH,-CH, a! I e) CH, CH, CH. cH, ety CH, seca CH,-CH-CH, 7*, Maconi uacreu Kap6ony i Tiaporeny 8 Mosexyati oxcurexosmicuoi opraniynoi cnomyku cra- HopaaTs 52,17 i 13,04 %. Ycranonits monexyaspry @opmyay pevoBHHH, Hanuuire ii cTpyK- TypHy dopmyny. Akio ua peyosaHa Mac i30MepH, CKTaziTs ixHi cTpyKTypHi bopmyzu. 8*.Jaramua dopmysa omHoro 3 Gararoaromaux cnmptis — C,H_.:0,, MonapHa Maca— 92 r/Monb. Yctanosits hopmyzy cnmprty. ‘Ypox Ne 8. Y3aranbHenus 3HaHb 3 BHBYEHO! TeMH. 3axHCT MpOEKTIB 1. Knacndixyiire pesosnnn, HaniscrpyktypHi (opmysH AKHXx HaBeneHo, i 3anoBHiTS TabnHITO: 1) H,C-CH-OH; 2) CH CH cs a 3) CH-CH-CH, ; H,C-CH, cu, cu, CH, Fb Lo 4) CH, CH, CH,; 5) CHy e008: 6) CH;-(CH)),-CHa; CH, CH, CH, 7) G-CH,-CH, ; 8) CH. -CH-CH C70 oe 9) CH, CH,-OH; C-CH,-CH, CH,-NH, cH, 10) CH, ee NH, Hacwuennii pyraezo1eHp Henacwaennii syrnesoyenb Compr Kap6onona kucnoTa Awinioxnesora 232. Tloscuirs, a Moxyrs Gyr i30MepaMn ByrnenosHi 3 TakuMH KapSoHOBHMH saHIOraMH: wee HOPMaNbHUMU, Oo H-anKAHANtL, CH,-CH~CH;-CH,-CHs CH,~CH,-CH;-CH; H-neHTaH n-6yTan Ankanu 3 poseanyocenum Kap6onosum aanyiozoM, ioMepHi HopMareHuM, HazueaIomD i30- MepHUMU aaKanamu, a60 ioanKananu. cH, CH;-CH;-CH,-CH; CH;-CH-CH, n-6yTan iso6yran ‘Zina yropena nase opranisnux cnonyk Haiisactime suxopucroByiors cHcTemaTHuny (Mix- napogny, IUPAC’) Homenxaatypy. Haseu ajkanis Heposraayxenoi Gyaosn. [epmti sorupu wreHH romoaorisuoro pay aa- kanis MaioTs mpusianoni (Tpamnuiiini, icropwaHi) Ha3BH: meman CH,, eman C2Hs, nponan C3Hg, 6yman CsHho. Haspv HacTyMHHX wWieHiB yTBOPIOWTs Bi TpelbKAX 4HCIBHEKIB, Wo BiNMOBIZaIOTS KiBKOCTI aromin KapGony B 7aHiyosi, 1os1a104H cytpiKc ~aH: MeHTaH, TeKcaH, TenTTaH, OKTaH, HOHAH, HeKan., Jaa yreopenns nase aakanis posranyxenol Gyx0BM BuKopuctosyioTs HasBH arxinonux samicnurie. Aaxinonuit samicuux — ye sanauox (empyxmypnuit dpparmenm), wyo ymeoproemeca nican yrenozo eidoxpemnenni amoma Tidporeny eid moaexyau anxany. 3azanna dopmyna— CyHoms1 jz). Smo cknay atkinbHoro 3aMicHHKa He Mac 3HaYeHHA 11 KoHTeKcTy, foro inogi nosHayaIOTS aaTHHcEKoWO stiteporo R?. Haseu askinbHyx 3aMicHnKis yrsoproirs saminol cydixca -an y HasBi BiznoBiqHOrO® amkany Ha cydixc -w7 (-i1). PosriaHbMo CXeMH YTBOpeHHS Ha3B aIKiIbHMX saMicHMKiB Aa Tep- ‘MINX BOX anKAHiB: aka aakinbanii 3aMicHHK akaH @QIKUIbHHi 3aMiCHHK HO H HH HH HCH] HC CH] > HC H HH HH eran eran emus ' Mixuapoauuii cows pyuaamenransioi ta mpuxnaguoi ximii (aura. International Union of Pure and Applied Chemistry, IUPAC) — mixvaponwa Henepwasia opranisania (1919 p.), aismuicrs axoi cupamo- avid Ha pOIBHTOK xioii ax Hayku. Bona 06’eauye HawionanbHi ximivmi TosapHcTBa. 2 Paduxan (R) — sazeuuaii necmitixa wacmuna Monekyau 3 Hecnapenum exexmponom: *CHs; *CzHs. Moust- TA He TOTOHe NOHATTIM arxinonuil 2amicHux i ayenesodneaut saichux — hparMeHT MomeKYAH, WO 3a- simmaetses ricns yaBHoro BixOKpeMuIeHHA aToMa Timporeny Bi MOMeKYsIM BYTNeBOAHIO. > Binnosigunii» — tyr i zani osHa4ae «@ TaKoWw camoto KinbKicTIo aToMis KapGony». 25Tpasuaa yreopenua ua3p ankanis posrasyaenoi 6yzonn. 1. 3a ocHony Ha3BH ZaHoi cnomyKH GepyTs HasBy ByTeROAMO, aKa BinMOBiAAe HHCTy Kap- GonosHx aToMis romoBHoro NaHtora. PonoBHHM aBLFOrOM BBaKAaIOTb: 8) natizosumit; 6) naiicxnayninmit (3 aaliGimmor xineKicro posraryxxeHs): CH; 3a HasBHOCTi 1BOX 4H NeKINIBKOX O/HAKOBHX 3aBNOBKKH NaAMTOTiB 3a TOMOBEM BHOUpAIOTS ganmor 3 HaiGinbwo1 KinsKicno posranyxKcHs. 2. Tlicna Bcranoprenua Tonosnoro nammora atomn KapGony Hymepyiors: CH,'CH~CH,~'CH, ‘CH, *CH, 'CH, a) nymepautito TownnaioTs 3 Toro Kinns, 10 aKoro HaliGnmxue postamonaunit Oymb-nKMi an- kinbamit 3amicumx (npunyun naicmentuux noxanmie’): “CH, "CA-CH,~'CH,‘CH,"CHCH,-'CH, ‘CH, "CH-'CH;-"CH,—"CH,"CH~'CH,—'CH, CH, GH, CH, CH, HeIpAaBWibHa HyMepattia npaswabHa Hymepais 6) akwio anxisbHi 3aMicHukH po3MinicHi Ha oAHAKOBIMi BiAcTaHi Big KinMiB, TO mig Yac BUOO- Dy HyMepautii KopHctytorsca anhapiTHHM nopsaKoM (erHa — MeTHA...): cH—CH~cH-CH~CH-CH, ‘cH-CH-CH-GH-cH—cn, CH, CH, CH, CH, sexpanionia paces pasion nyepit 5) AKWO Ha omHaKORIii BincTaHi Bin Kinin posMimeni OAHAXOBi anKinbHi 3aMicHMKn, TO HY- Mepantiio arene Sa xinus, ne € Gimsmme posranyxens: ‘cH ~CH.CH,CH~CH, cH, CH, Henpannmena Hymepantis papwibHa HyMepantia 3, Y nassi cnoaykn sasnayatoTn: a) 3amicunxn, nepepaxopani B andanitHomy nopayKy: © nepen Hazpo10 saMicHHKa BkAa3yIoTS HoMep atoma KapGony, Gina axoro posmimennii an xinsunit 3amicuux; © axmo HeOGxigHo Bka3aTH KinbKa O”HAKOBUX 3aMicHMKiB, TO BHKOPHCTOBYIOT MHOHHHE npedixcn: du- (di-), mpu-, mempa- (ix we Bpaxosyiors y Bu3HayeHHi anbasirHoro nopanKy); © qOKaHTH OqHAKOBHX saMicHHKin gamicyloTs y TlocaiAoBHocTi sGinsmcHHE HHCRa i BInO- KPEMINOWOTS OHH Bil ORHOTO KOMAMH; AKIO 48a OAHAKOBI QIKIJIbHI 3aMiCHHKH Po3sMimeni Oma aroma Kap6ouy, To 4uc70 cTaBAaTS ABI‘; NOKAHT Bi HASH ANKizbHOTO 3aMicHHka (i HaBNAKH) Bi- Hoxpemmorors pebicom; oxéinm — wciose abo Gyxsene nosnavenna amona KapGony eoaosnoco nanyioea, kum ykazyiome po3- mauyeanna samicnuxie, xpammucc 36'askie i cmapwoi xapaxmepucmuynoi apynu wodo podonauarsuo’ cmpykmypu, TOGTO CTPYKTYPH, AKA CTAHOBHTS OCHOBY MONEKYIM CHORYKH (VIA CHONYK aMMKMIMHO! Gy10~ BH PONOHAYAMBHOI CTPYKTYpowo € rosOBHHG KapGoHOBHit naNWOr). Ha nHcbMi AOKAHTH po3niNMOTs KO- manu, Ha Hamux cxemax 1OKaMTH HosHa‘ieHi BHM BepxHiM inIeKCOM, 26 i |© Ha3By OCTAHHBOrO aKiIbHOTO 3aMiCHHKa IMIyTS PasoM 3 Ha3BOI0 TONOBHOTO AaMMOra; 6) Ha3By ankany, ska BignoRisae rosOBHOMy KapOoHoBoMy AaHInOry: CH, rH, CH a E ‘CHC C ~'CH,“CH-'CH~'CH, ‘cH, “6 *CH,-"C—cH,-"CH, CH, cH, et, RCE 4-erun-2,2,5-rpamermrexcat 2,2,4,4-rerpamermurexcant Tipwkanag 1, Cxnazaemo nanisctpyxtypxi bopmy.m isomepaux Gyranis. Cnowarxy sanmeyemo Haniserpyxrypuy dopmysy x-Gyrany, posmicrusum 4orupu atom Kap6ony p neposranyxennit namtuor i noaemo atomm Tinporeny. Hlo6 mepersopurn Kap6ox0- ‘suit sanmor Ha posranyxennii, nepemimyemo versepruit arom Kap6ony 70 apyroro (Mitinoun Hioro icusma 3 atomom I'igporeny). CH, CH, (CH;-CH,-CH,-CH; CH,-CH-CH, n-6yrant iso6yran (2-merummpomati) Tipwxaag 2. Cxnagacmo naniscrpyktypxi bopmynn isomepxux nestanis Ta Ha3BeMo ix 3a CHCTeMaTHYHOIO HOMeHKTaTYpOW. Hy cH, ‘cH "CCH, eee Tae (CH3-CH;,-CH,-CH;-CH; (CH,~ CH- CH,‘ CH, cH, HeTICHTAK 2-merua6yra 2,2-muwermmnponan Buxonaiime sasdanna 1. Hanmmire naninetpyxtypai popmysn: a) H-1 TeKcaHY; 6) 2-meTuanponany; B) 2,2-aqmmeTusanenTany. l : : eR a Lobel | ieleese | Li i | | | | it T | Por | | ol. de aetes 2. Yxaxirs cnonyKH, HaniscTpyxTypHi PopMysIM AKHX HaBeCHO, m0 € CIpyKTypHUMH isomepamn. Hasire ix: CH, a) CH,-CH,-CH, 6) CH. -CH.-C-CH, CH,-CH-CH, cH, see! 8B) CH—CH;-CH-CH, 1) CH, -CH-CH-CH, cH-CH-CH, cH, CH, CH, 3. Hassin» ankax, uaniserpyxrypsa dopmyna akoro CH,-CH-CH-CH,-CH-CH-CH, CH,-CH, CH, 27CH.-CH,,_CH,-CH, 5. Hassirs syrnesonent, 3 uariserpyktypHow hopmys1010 ca is me Py CH,-CH,”~CH,-CH, 6,Hanuumsits waniscrpyxrypai opmyan: a) 4-erun-2-meranrexcany; 6) 2,2-amwermanenrany; 8) 2,2,3,3-rerpamerua6yrany; Tr) 2,2,3-rpmmerua6yrany; 2) 3-cru-2,2,4-rpameranrexcany, e) 4-eranoxrany. Seaueunea z { betes bd coleet 7*. Cxsanirs etpyetypxi opmyan 1ps0x isoMepHHX ankanix, ronoBHHit kapGonoBHi nator aKuX micrurs cim aTomia KapOony. Taxox Mosiekya MicTHTb aikitbHi SaMicHHKH: onmH mpontin, Ba erwin, soupy MeTwm. HasBite ui ByrneBomHi. Tecmosi saedanna CH, CH, T T 1. Yxaxitb nasBy Byrsienomm0, aaniserpyktypua dopmyza, akoro CH-CH-CH-C— CH, GH, CH, A 3-erm-2,4,4-1pumermmentant ABB B 2,4,4-1pumervii-3-ermanentan ]| B 2.2.4pumernr3-erminenran TP 3-merwr-2,4,4-1pumermmesran 2. Yeaxirs Haspy ByraesoqH0, Mone sKoro A C.Hio B CsHio B CsHi. T CsHs a 3. Yeaxxirs HasBy ByrieBogHiO, HaniscrpyKrypHa opMysa, AKOTO ae ie oo HC, CH, A 2,3-nietnn-3-metan6yran B 2-erun-4-merumentan ABBT B 3,4-auweruarexcan T 3,3,4-spumeruarercant i ‘Ypox Ne 11. [pakruane 3anatra 1. Hasire anxann, crpyxrypui opmyau aKux: CH CH, a) CH,-CH-CH-CH, 6) (CH,-CH,-C-CH,-CH, CH GH; tk CH B) CH,-CH,--CH, 1) CH,-¢-CH, GH; na 282. Hanmmirs wanisctpyxtypxi dopmysm: a) 3-ermi-2,3-numernanentany; 6) 3,3-nierH-2,2,4- ‘qpumerunrenrany; 8) 2.2,3,3-rerpamermarenany; r) 2,3,4-7pHM: Fea Prec = eas bese | | L fas pails 4, Hanmmits nanizerpyxrypui aukaniz posranyxeHoi youu, Monexysm 2Kux MicTaTE 9 aromis Kap6ony, n’sTs is HHX yTBOprOIOTL ronOBHHi KapGonoBuii Tanmor. Haspirs ix 3a cH- __CTEMAaTHYHOI HOMeHKMaTypoto. aiteh Bo he md 4 ] i! ] oa Fy et | L. | fea ete z | et Pare T | Ine a | | Seal . cL ; + Sica | [ | | { | 1 L i pant Poa ferbs}ovlonfonhada ato safal oad ch i ale aaah = + i | | peers Eases 5. Yxaxite ii ycno noscuirs 4H ¢ HaBezeHi peyosHHH isomepamu: a) 2,2-mamerun6yran i 2-merun- nentan; 6) 3,4-gieramoxran i 3,3-q4MermmHonan; 8) 3-ermimentan i 2,2-a4MerHameHTaH; 1) 2,3,4,4-TetpaMeruarexcan i 3-erm-4,4-nuMeTHIIreKcaH. 6*. Macosa 4actka Kap6ony 8 Monekyai amkany craHoButb 83,72 %. Yctanosits toro MomeKy- RapHy dopmyny, HanMmits HaniscrpykTypHi opmysH Bcix i30MepiB i Ha3BiTE ix 3a cHcTeMa- ‘THUHOIO HOMeHKAATypoI. 7*. Yewxirs cucreMaTH4ni Ha3BH akaHiB posraryxeHoi Gy,0BH, MOueKYsIH AKHX MicTATb 8 aTO- min Kap6ony, pu 3 aux e 8 cxnati ankinbHux samicnuxis. Tecmosi sasdanna cH, CH, 1, Yxeoxins waaay pesonusut, uaninctpystypua (bopmyaa skol CH-CH,-CH GHyas new, A 1,1,3,3,-tetpamMetannponan B 2,4,4-numermamentan ABBI B 2,4-qumermmenran T 2,2,4-1pumerma6yran OOOO2. Yeaokirs rpyny pesoeua, aka Micrrs ame isomep A 2-merarexcan; 3-meraurenran; 3-er1irexcar B 2,2,3,3-terpamerun6yran; 2,3-numetmirexcant; 3,4-aqumermarexcaxt B 3-ernnrexcan; 2,2-qumernanenran; 2,3,4-1pumeTaarexcan T° 2,3-auermaGyran; 2-merumenrant; 3-Mermarexcan o> CH, 3. Veaxirs naspy pevosin, uanincrpyxtypHa dbopMyata aKoi CH,~C-CH,-CH, CH, A 2-ermn-2-merun6yraxt B 3-ermn-3-mernn6yran ABBY B 1,]-qumerun-2-eruanponan 1 3,3-ammermmenrax 4, Yeaxxins ryermmy 2-merusnponary 3a oBiTpam A 1,45 B 1,52 B20 T 22 Ypox Ne 12, Ximiasi Baacturocti ankanis Ankanu 3a cranaapramx yMos — ximiuno ineprHi pedosnam: He B3ZeMOTiNOTE 3 KMCTOTAMH, ayramu, 3 KMnO, (ciutbHHM OKUCHUKOM). 1. Peaxuil 3amimenna (rasorenynanns)'. BsaeMmodiro opeaniunoi pevoeuru 3 zanozenom nasueaiomb peaxyiew canozenysanna. Tlin ac ranorenysanua ankaiis siuGysacrsca 3amitienna aroma Pimporesy Ha atom ranore- ny—F, C1.Br — 3 yimopedan eazozenoaaxany. Posraanemo eli npouec Ha npHKaai Meany: a H U pemney i t 1) H-CHH+ Circl * H-C-Cl+ HCI; 1 2s H-G-C1+ HCI H H a so1opomerar awxtopomeran a cl cl Lp vs ‘ hy. b 3) HCH GC! > H-G-Cl + HCL; —& C-¢-Cl+HCl. a a cl ‘pinuiopomeras ‘Terpaxnoponerau 3a yMon sHauHoro HaqTMUNcy XTOpy peaKuis saRepmIyeTsCR TOBHHM saMinenHaM arois D'i- nporeny. Ilo nosumii xapSonosuii aanmor, To erme RixGyRAcTECs 1x peaxuia. Y moseKysax HITASHX arikani (METaHY, eTaHy, MpOraHy) 3aMimyrarHce MOxyTs mocmistoBHO yci atomu Tixpo- reny. Le o3Hauae, 10 B Momexyai Merany aroma Xnopy Moxyrs 3aMicTHTH OHH, 1Ba, TPH aGo nei uoTHpH aroma F'inporeHy, saiexuo ail BiaHOMeHES Kim-KocTelt pedosMHH pearcuTi: 1) CHy+Ch oa CH;Cl + HCI; 2) CHy + 2Cly ee (CH,Cl, + 2HCI; 3) CH, +3Cl, “5 CHCl +3HCl; 4) CH.+4ch > CCl, +4HCL 2. Peaxuii oxucHenHs aikaxis KicHeM BiAGyRaloTECs 3a BHCOKHX Tewmeparyp. Tit 4ac ro- pina suninactsca 3uaiia kinbxicrs TenoTH: CH, +20; + CO; +2H,0; AH<0. SIkmo KUCHIO He BHCTAYAE JL1A TOBHOTO OKHCHEHES, TO cepen nporyKTis peakuii BUABNAIOTE aauuii ras (CO) i syrneus (C). 3. Tepmiunmil poskaa. SIkuio cibHo HarpirH Merax 3a BicyTHocTi noBirpa, To BiH po3- kuranacTacs (sanexHO Bi TeMnepatypHl) 3 yTBOPeHHAM pisHHX MpomyKTiB: CH, SOR 2H aGo 2CH, 20°C, C,H) + 3H. ' Cepen peaxuiit ratorenysanus Buaitsors ua THM peaxuiii: peaxyiT zaniwyenns, aKi BTacTHB ankanam, 1 peaxyii npucdnanne, axi xapaxTepHi JUIN HeHACHNEHEX ByTIeBOHID. 30Tlin, sac Tepmisnoro poskiagy inmHx ankaxie (Big nponaHy i BHI) yreoprororsca HacHueHi ii wenacwieni Byrnesogni (axi Malors KopoTumi KapSoHoBi JaHIMOrH, Hi MOYATKOBa petoBHHa). Taxox Moxe Bin6yraca mponec dezidporenisayii — wiamennenna atomis Tinporeny — 3 nepe- ‘TBOPEHHSM HaCHYeHOTO BYTICBOAHIO Ha HeHacHueHMi: CH;-CH,-CH,-CH, —" CH, + CH;-CH=CH, 4, Bomepuzanin. Tomepusauin — ye peaxyin nepemeopenna ximiunoi cnoayku na it cmpykmypnuit izomep. 3a neBHHX yMoB ankaHH HeposranyxeHo! GyT0BH, IMO MicTATS He MeHIe YoTHpbOX aToMiB Kap6oxy, nepersopioorses Ha isomepui crionykH 3 Posraayxenma KapSonionin sratmoroM: 5 , AIC, asa ee CH,-CH,-CHy-CH; CH,-CH-CH, Gyran 2-mervamporiat (s06yran) Buxonaitme sasdannn 1.3 Hanenennx dopmyn BuGepirs dbopmynH ankanis Ta HasBiTh Ix: C\gHz9, CyH20, CsHis, CrH22, onepxan eren, Hanmuirs pistania p 3. Hanuurite pisnanna peaxui isomeprsanii n-nentany i Hassite mposyEr peaxiil. | pale il T 1 ia | Lol el a Iiehie ae iced wise piel i Cas eee Pe eee e | L L Lol L ge ee os 6. SIxuii 06°em TioBiTpa (x. y.) HEOOXimHO BHKOpHeTATH AAA crramtO1 i 0,8 mom merany i 0,04 kr evany? eee ere ee STM Lee ee Det poet t | babes ep _| L pe Zt sr Versace’ ‘wonexyaupay eomaty ‘amkay, yuacnigox cnamopania 15 1 aKoro BuAimocE 45 1 xap6on(IV) oxcmny. Bustipy Buxonano 3a O2HAKOBHX yMoB (yCHO). 9*, YeraHopirs Monexysapuy opmyny amkany, Ha cnamosanna 51 sKoro BuTpaTum 32,5 a KHCHIO. BUMipH BHKOHAHO 3a O7HAKOBHX YMOB. 10*. Cyminr nporany, merany Ta KapGon(IV) oxcuay saiimac 06’em 6,16 2. Iicnt cnamosanna cymimi B Hammmmy KucmIo onepxano 11,565 1 KapOon(IV) oKenay. Ycraronins o6’emny wactxy (%) nponany B cyMimi. Yoi BAMipH BHKOHaHO 3a OAHaKOBHX yMOB. Tecmosi zaedanna 1. Ykaxire ankan, sknii He Mac isomepiB A nenran B nponan B 6yran I oxran 2. [ja nacienmx yrenoquin xapakrepHi peaxuii A mpneqnanms, samimenta, maaemonil 3 nyrann B npneananna, repmisnoro poskaaay, ssaemonii 3 KUCTOTaMH B okwcnenns kamili nepManranatom, TepMidHOro posKiajly T° samimenus 3 ranorenamn (Bry, Fs, Cl2), tepmissioro poskany, ropinns 3. Veaxirs Monexyaspny opmysy uxopoerany A GHCI B GHCh B CHCl T CHC; | | dy ' | | ABBT 324. Yeaxits Tun ximidHoi peaxuii, 10 sKorO HaNexKHTb peakiia XOpy 3 MeTAHOM A o6minty B cnonysenns B samimenia T° posxnany 2b 2 L 5. Yeaxire opmyny HacweHoro ByTsIeBONHIO A CosHso B CosHsy B CysHs2 T CosHas 6. Yeaxxirs, axwii 3 syrsrenoqnin mac naiiGinomy Kinbxics isomepin A rexcat B renran B nonan T nexan 7. Yeaxirs simnocuy MoreKyaapuy Macy opraxiunoro upoayxty peaxuii xaopynantx erany, sKiN10 kimbxocti pevosn xaopy ii erany BimHocatscs aK 3 : 1 A 64,5 B99 B 133,5 T 168 Ypox Ne 13-14. Beranopnenusa MomekyaipHoi PopmyiM peswosnnn 3a 3araIbHoW dopmy.101 romosoriunoro psty Kopucryouncs 3aramuow dopmy010 ankanis CyHyn+2, MoxHa BcTanopuTH KiabKicTs atomis Kap6ony ii Tigporeny 8 Mosekysti Gyb-AKorO HaCHYCHOTO BYTNCBOAHIO 3a YMOBH, [110 Bi- OMA Bi{HOCHa MOJIeKYJIAPHa 4H MOsApHa Maca crlomyKH. MosapHy Macy cromyKH MOxKHAa po3spa- XyBaTH 3a BiOMHM sHaueHHAM rycTHHH 4H BiAHOCHOI rycTHHM (3a BOAHeM, remieM, nOBiTpaM). SIkmo x PeyOBMHA € HeHACHYHHM BYTMeBOAHEM, TO KOPHCTYIOTHCH 2aPaTbHOW (POPMysIOI JL ankenia CyH2, a60 ankinin CyH2y-2. Axmo 8 3asayi fetsca npo ranorenonoxiani Byrmenon- nip, To cKNaqaioTS BiAnoBiani sarambni @opmymu. Hanpuxaag, w06 cknactH sarambHy dopmysry ‘TerpaGpoMonoxisHHX aNKaHis, y 3arabHiit bopMysi amkanis yoTupu atomu Tiporeny saminy- 1OTb Ha YOTHPH aTOMH Bpomy: CyHonea + 4Bty > CyHo,-2Bry + 4HBr. 3agaya 1. Mossapxa maca ankany craHosurb 100 r/Moz. Yeranonit, Momexynapuy bopay- AY BYTNIeBOAHIO, Aan: M(CyHon+2) = 100 r/mons CoH2nt2 —? Pose’asanua 3aransua cbopmyna ankanin CyHon+2. 3Ha1o4n MosaapHi Macu Kap- Gony it Diaporeny (M(C) = 12 r/moms, M(H) = 1 r/mons), cxnaa- €MO piBHAHHA Ta po3B’sKEMO Horo: 12n+2n+2=100 aes) Bianosiap: Cis. 3anaya 2, ycruua ankany 3a nositpaM cranosurs 2. Yeranonir Moaekyaapuy dopmyay ayrsesomiio, Ha3sirs iioro 1a Hanuutirs Hanisetpyxrypry opMysy, 3axKaIou Ha Te, 10 Bit Mae posranyxermtit KapOonosuit naHtor. Hau: Po3e’asanna Daop.(CaH2n+2) = 2. | 1. 13 bopmyam ans pospaxynky ryeTHHn rasy 3a MOBITpAM: M(CyHsy 12) CHiata—? Daos.(CoHan+2) = atgony pospaxonyemo 3HaveHHA MonspHo! Mac pevosmun. M(rios.) = 29 r/mom: M(CpH2n+2) = Drros.(CaHan+2) * M(non.) = 2 - 29 = 58 (r/moms) 2. Cxnanaemo pisaanua i po3e’ssyemo fioro (M(C) = 12 r/mom, M(H) = 1 rimoms): 12n+2n+2=58 n=4 Opxe, monexysapua bopmyza ankany — C,H,o. Le 6ytaH, onHaK BpaxoByrouH, U0 BiH Mae po3- ranyxeuuii apGoxosuit amor, 1e He #-Cyrax, a fioro isomep — iso6yran (2-meTamporiaH). CH, T Birnosian: CH;-CH-CH; . 33 *3 Bepesait O. Xinsix. Somr-noci6mm. 10 x:Bagaya 3. Tycrusa anxanty (3a u. y) Cratos 1,964 r/n. Yoranonins uel anxaxt. ano: Poss’asanna p(Cotlon+2) = 1,964 ria __| 1. Kopuerytoanes dopmyzio1o 18 pospaxynky rycrunu rasy: CaHon+2 —? ol CyHanta) = 2 {Sattzt2) 1 oGuntesoeMo MonapHy Macy amrkany. Viy = 22,4 s/Moab: M(CyHowa) = p(CaHan+2) * Vr= 1,964 * 22,4 = 44 (r/ons). 2. Suaxaioun va saranbuy hopmyny anxany (CyHon12), Ckitaytaemo piBAHH Ta posB’zyemo Horo (M(C) = 12 r/wonp, M(H) = 1 r/woms): 12n+2n+2=44 n=3. opmyaa syrmeponmo C3Hs. Binmoniae: C3Hs. Bagaga 4. Tyctuna sunapis anGpomonoxianoi ankany 3a amowiaxom cranoswr 11,06. Yeranonits moxexynapay opmyzy cnomykx. Tlaxo: Pose’asanun 2 Dyu,(CaHanBry) = 11,06 | 1.15 bopmymr ana pospaxyxky rycrusa rasy 3a aMoHiaKOM CoHoBry —? BYeMo 3Ha4eHHa MonapHoi Mach cnonykn. M(NH3) = 17 r/omp: inBr2 — ? : M(CyHon Bo) Dyu,(CnHenBr. crit M(CyHinBr2) = Dyy,(CaHnBro) * M(NHs) = 11,06 - 17 = 188 (r/monp) 2. 3haioun Momspai mach enementis (M(C)= 12 r/vons, M(H) = 1 r/momt, M(Br) = 80 r/mon), ckafaeMo piBHsHa Ta posB’ssyeMo foro: 12n + 2n + 2-80 = 188 n=2 Orxe, dbopmyza qH6pomonoxizHoi ankany — C)H.Br2. Bignosige: C,H.Br. 3anaua §. Macosa wacrka Bpomy Monexymi an6pomoankany cranosurs 69,57 %. Yerano- nits MoaeKysapuy opmyzy cnoxyKn. Mano: Pose’asanna 1.13 bopmynn ius pospaxyHky MacoBoi 4acTKH eslemeHTa B peyoBHHi PospaxoByeMo BITHOCHY MomeKyslapHy Macy cnomyKH: 4, (By x NB» MABE dl (GED Bin? ae N— xispxicts aromin Bpomy 8 Monexyni au6pomoankany. MypCoHmBr,) = 4-BO* NCH ou B9 Boxe CyHanBr2 — ? = 230 Onxe M(CyHinBry) = 230 r/monp. 2. 3naiown monspxi macn enementis (M(C)=12 r/moas, M(H) = | r/moms, M(Br) = 80 rion), cku1aacmo pibnanna Ta poss’ a3yemo iioro: 12n + 2n+2+80=230 n=5 opmyaa m6pomonoxianoi anxany — CsHyoBr>. Bignosign: CsH,oBrp. Buxouaiime sasdanna 1. Yeranonirs Moaexynapuy opmyay alkany, rycTuHa aKkoro 3a reniem 11, Ta o6uncHiTE O6’em emo, Reoxizuntt ans nosoro oxwcHenHs 0,5 Mom® uBoro anKaHy, eS ota— +4 a 8 : = 2 € a | Bo is i 2 ee ee 5 2 @ rm a : ' PH E[ 3 3 he ee : Bo eeeceHe Kee HECEEEEE SS CeCe Eee Eo - ae ag a ree ci Bo BEE 23 $4 hy TET Fae eee Eiji ttiigs pte ae — ] e Tel BE alot Be re I PREECE Cee —a gel Pay rie, ' |abetsd)? ad | ik Peo eet fe aE az | 38 ; 2mMich Tales rt eee } | | It — a ot Lae 6. Macosi sactku Kap6ony i Xnopy 8 ranorenonoxiqHili ankaHy CTaHOBIATS, BiATIOBIAHO, 71,72 %, Fycraua ii sunapia 3a novirpam cranosurs 3,414. Yeranosirs MoneKyaapHy ay peyosunn. si {e5p ct | oe | | f ch 7 Mozspua aca ogHoro 3 ankenip cTaHOBHTE 70 r/mom. 3aranbHa dopmyma aulkeHiB — Yerauosirs Monexyampuy dpopmyay peyosntn. (YcHo). 8. Macosa uacTka Bpomy, m10 € y cknagi au6pomonoxignoi Hacm4eHoro ByrneRomHo, 79,2! ___Yeranosits Pees MeL rin : i} ' Pet I et | tel 1 ses} 2 |. Hammuins pinnans peaxuili, 3a ixMMH MoxHa 3nilicHHTH Taxi TlepeTBOpeHHs: joeran —> 1,1-aH6pomoeran — 1,1,1- T | ee. r | seh um 1,68 1 sae erany i mponany, onepaxamt 4, 480 Byraekucnoro rasy (H. y.) Yeranonirs o6'emuy uactey (%) mponany B cymiui. 12*. Ycranosirs opmysn 7B0x weHis romonorisHoro pay alkaHiB, WO BiapisHAOTECA Ha atomu KapOony, ski10 MoupHa Maca MoHOGpomonoxigHoi oj Horo ByrneBoHO B 1,34 Gimpma 3a Momapry Macy Moo6pomonoxiquoi inmoro ByrneBOaHIO. 36Tecmosi sazdannn 1. Y«axirs dbopmyay Hacwiexoro ByrnesoHI0 BBY A CoH B CxHsy B Cue T Coole Ae 2. Vewxire bopmyay Tpuxtopoerany A GHsCh B GH,Ch B GH;Ch T GH,Cl 3. Yeaxirs nacuennii syrnesonens, axuii He mac isomepis A 6yran B nenrax B rexcan T eran 4. Yeaxits hopmysy syrnesoamo, skit Mae Halimenmry KisKicre isomepis A CoH B CHo B CyHn T His 5. Merait ne petynac B peaxutii A oxucnenns -&B 3amimenna BB _posknany T isomepusanii 6. Yeranosir pevoaunn X i X, y peaxnit X + 3Xy — CHjCh + 3HCL A GH, CCl, B CH, CHCl, ABBIr B GH, Ch T GH.Cl Ch 7. Yxaxits HaniserpyxtypHy (bopmysty 2,3-qumerun6ytany A CH,-CH-CH-CH, B CH,-CH-CH-CH,-CH, CH, CH, CH, CH, an B CH,-CH, CH, 1 CHy-C-CHsCH, CH,-CH-CH, cH, CH,-CH, 8. Years naspy anxany Taxol 6yzoan: CH,-C-CH, CH,-CH, A 3-merun6yrax B 1,2,3-rpumerannponan BBr B 2-erna6ytan TP 3,3-aumermmenran OOO Ypok Ne 15. Ankenn ii ankinn. CuctemaTauna HoMeHKaatypa. CrpyktypHa izomepia Byenesooui, monexyau AKux saioms nesamcnenuil KapOonosuit ranyioe 3 odnun nodsitinun 36'93KOM, Hazueaiom aakenamu, Zazanoua popmyna —CyH3y (n > 2). Eren C,H, i nponex CH, — nepmti unenn romosorisnoro pay anxenis. Byenesooni, MOneKYIU AKUX MaIOM» HeZaMKHenuit KapGonosutl naKYI0e 3 OdHUM NompiiHUM 36'93KOM, Hagueaiom® aakinanu, Zazanona hopuyna —CyH2n.2(n 2). Erux CH; i nponin CsH,— nepuri wenn romonorinoro paay ankinin. Cucmemamuuna nomenxnamypa aakenie it anxinie 1. Jas yreopenna cicremarnanoi HasBH HeHACHYCHOTO BYTsIeBO/HIO Heposrasty:xeHo! Oy OB: a) Bu3HaualoTs atom KapGony 3 HaliMeHIIMM NOKaHTOM, Git aKOro posTaMloBanHii KparEult 3B'530K: 'CH;—?CH = *CH — *CH,~*CH; 'CH,=*C =4C —‘CH,—*CH, 6) samimorors cyixe -an anxarry na cytpixc -en (a8 ankentin), aGo -un (-in) (ana anxinin); 8B) BINOKPeMMOIOTE TOKAHT Biz KopeHs i cyikca peicom: ‘CH;—?CH =*CH - “CH, -*CH; 'CH;—*C =*C -*CH,-*CH; nent-2-eH nnewt-2-m 372. [| yrsopenns cricTemarHinol Hasan HenacnueHoro RyrenommMIO posranyxeHo! 6yT0BH: 1) BHOnpaioTs Haiiqosmnit xapGononuit namuor, akuii MicTHTS KparHuli 3B'a30K: CH, 2) uyMepanio nowpHaiore 3 Toro Kin, 10 #KoTO Haii6mpK4e posTamoRaNHii KparHuit 38"A30K (sriaHo 3 MpHHUTOM HaiiMeHMHX OKattTiB): CH,“C~'CH,"CH,"CH, 'CH.C#’CCH-*CHCH, ‘CH, CH, a) ako B MoneKy:ti crloayku KpaTRUi 38’a30K pisuoBiquateHnii Bin O60x KinuiB KapGoHO- Boro saHora, TO HyMepautiio NOYHHaWTS 3 Toro Kina, HO sKoro GuwKIe posTaMoBaHHii ankistb- unt samicnux: iG *CH-CH="CH~'CH,~“CH, 'CH,“CH~’C="C—'CH,"CH, CH, CH, 6) aKWO B Monexys1i chonykH KparHHit 3B’a30K pisHosiagancunit in OFX Kinuis Kap6oHo- Boro nammora, To y suGopi Hymepamtii KopHoTyIOTSea ambabirHum nopasKoM (eTHT > MerH — nponia): ‘CHC : ‘CH “CH="CH~"CH-CH,"CH, CH, cH, 3. Y nassi cnomykn 3asnayators: a) samicuuKu, nepepaxosani 8 aasiniomy nopanky, #K i y BHmanky 3 ankanamn (BizoKpemsteHi oan Bin oHOrO KoMaMM Ges npoOiia, a Bi KOPeHA HeHaCHYeHOTO ByrneBom0 — yepicom); 6) Hay HeHacHHeHoro ByrmenomHO, aKa BiMMOBiZae TONOBHOMY Kap6oHOOMy slaHINOry (Kopine) + Gmoxsii 70 nowaTKy AOKaNT KpatHoro 3B'saKy + cyike —en (su1a aNKeHiB), aGo -un (ix) (ana ankinis), axi Bizoxpemmotwrsca ofHn Big onHOTO Zedicamn: CH, CH, ‘CHy OCH, CHCH='CH *CH-'CH,“CH, 'CH.-C—'C='CCH"CH’CH, ie cH, 1H, 3-ermus-6-meTus0KT-4-cH S-ermn-2,2-numernarent-3-Ht Cmpykmypna isomepia anxenie it anxinis 7laa auxenis H auxinis xapaxrepya crpyxtypxa isomepia, 3ymosneHa posranyKeHHaM Kap- GoHoBoro naHMora i posTalysaHHsM KpaTHOTO 3B’ a3Ky. omepist anxenis. Y nepunx Box senis romonori4Horo paly ankenis — erexy i mporiery — isomepia Hewae. Crpystypua izomepi anxentia, y axix n> 4, Moxke GyrH symonena: ® isto erpyxryporo Kap6oHonoro aammora, axi Gysaiors Heposranyxexi (npami) si posranyaeni: © = posralllysaHHsM TogpiliHoro 3B’a3Ky B KapOoHOBOMy saHLyory (abn. 15.1). Ta6a, 15.1. Ha3eu nepuux mprox vaenie zomonoeiunozo prdy anxenie ma izomepie 6ymany Monexynapra Crpyxrypai Ha3pa ankeny |_tpopMy.ta ankeny opmyau ankenis 3a CHCTeMATHUHOW HOMEHKTATypoOWw CoHy CH.=CH) ereH CoH, CH;=CH-CH, nponen. (CH)=CH-CH,-CH 6yt-l-eHn Calls CH;-CH=CH-CH 6yr-2-en CH=C-CH, CH 2-mermanponer 38(Cxnayaemo nanisetpyxrypHi (dbopmysm Ta Ha3BeMo CTpyKTypHi isoMepH AIA peyOBHHH 3 MO- aexysapHor (opmys010 CsHjo. 1, 3anucyemo HanierpyxtypHi hopmynn 218 HeposranyxKeHux neHTenis Ta WasBeMo ix: (CH);=CH-CH,-CH,-CH; CH;-CH=CH-CH,-CH; nent-1-eH ment-2-en 2, Sanucyemo HaniserpyxtypHi bopmyam posranyaccHux isomepin y-reuTeHy Ta HasBemo ix 3a CHCTeMaTHYHOIO HOMeHKTaTypolO: CH, CH, CH; 'CH,"C—CH,"CH, ‘CH,-"CH-’CH-'CH, ‘CH,“C='CH—CH, 2-mernnGyr-1-eH 3-metun6yr-1-en 2-merun6yr-2-eH One, ¢ 5 isomepaux ankenia is hbopmys010 CsHyo. B ankeni taxox ¢ ii miockzacoei izomepu — nuktoamKann. Minexaacosumu bomepamu nazusaioms izomepu, Axi Hanesicame Oo inwux Kiacie (epyn) opeaniunux peyosun. Tluxaoankanamu nazueaiome anxanu, kap6onoei 2anyiozu AKux 3amKneHi 6 YUKA. Tlenten CsHjo Mae 5 i30MepHHX WMKIOaIKaHiB: CH, coh oH; ae SCH CHC, CH, CH,-C-CH, ih H,C—CH, CH,-CH-CH, — CH,-CH-CH-CH, cH-CH, CH,-CH, numsonenrart Meramtmncno6yran 1,2-aumerun- 1, 1-mmmern- erm uuknonponiast uuKonpona —_uuKoNportaH Orne, icuye 10 crpyxtypxux izomepis ana pesosun 3 bopmyno1w CsHo. Jsomepia amkinis 3ymosmena Gysoso1w xapGouoxoro nanmora i posTamysaHHaM noTpiiiHo- ro 3e’asky. B eruity ctpyxrypunx isomepis wemac. Y mportiny CH=C-CH, ¢ miaxxnacosnit isomep 3 Kacy PeYORHH, AKi HA3HBAIOTS amKadicnamu — nporiaytier CH;=C=CH)p. Le syrnesogni, axi marotb ananorivay sarambuy cbopmymy CyH2p-2 (n> 3), ane Monexynu aKUX MicTATS OBa NopBiiiHi 3B’a3KH. Byrun C,Hs — tperiit unex romonoriunoro pany ankinis Mae Apa izomepu: CH=C-CH,-CH; CH;-C=C-CH; 6yr--uH Gyr-2-mt Takoxxk € me 48a CTpykrypHi isomepH 3 Kacy aiKkazienis: (CH=C=CH,-CH; (CH,=CH-CH=CH, 6yra-1,2-niew 6yra-l, Onxe, 3arambia KibKicTb CTpykTypHHx izomepis peyosuH is dopmyn0w C4H, — 4. Buxonaiime saedanna 1, Haspits ankenn, HaniscrpyxtypHi bopmy1u AKUX: 7 CH; 8) CH-C-CH-CH, 5) CH,-C-CH-CH-CH-CH, CH, CH, cH, CH, CH,-CH, 8) CH,-CH=CH-C-CH, 1) CH,-CH,-CH-CH,-CH-CH, CH, CH=CH, 2. Hassirs syrnesousi, aniscrpyxtypxi hopmysm aKux romani HwKIC, 32 CHCTeMATHTHOI HO- MeHKaaTypoto: a) CH,-CH-CH-C=CH 6) CH,-CH-C=C-CH-CH, CH, CH,-CH, CH, CH,-CH, 39CH, cu, CH; B) (CH.-CH-CH-C=C-CH 1) CH=C~C~ CH-CH, CH, CH, CH, CH, 3. Hanmmirs naninetpyxrypri opmymu pyraenonnin: a) 4-metuarent-2-eny eras Nearer eee eee et 6) 2,3-aumerua6yr-2-eny 8) 3-ernarexc-3-eny 1) 2,4,4-1pumermanent-2-eny 4. Harmmuirs waninerpykrypxi bopmyan TaKux ByraeBorHis: a) 3-erna-2,7-aumerimnonr-4-mry 6) 3,3-anmermanenr-1-nny 8) 3-eTma-4-mermanent-1-HHy 1) nent-2-Hay $.Tycruua sunapis anxeny 3a nopitpam cTanopHTs 2,414. Yeranonirs monexynapxy opmyay auikeny. | e as 1 Monapua Maca onuoro 3 ankenis — 112 r/Moms. Yeranosirs moxexyaspay opMyay ankeny (yeno). 7, Hanmuirt uaniserpyxrypay opmyny ankexy, Monexyaa axoro mictur» 4 aromm Kap6ony it OsuH $ BUX — y ckalani anKibHOTO saMicHHKa, Haapirs foro.9*. Cymim MicTHTS Ba ByrneBOgHI, IO MaIoTE OMHAKOBY BiMHOCHY MoneKysapHy Macy. Tepumii ByriesoeHb — unkniuuuii Hacuuenuii, a apyruii — romonor ereny. 'ycruna sunapis cymimi 3a eTaHOM cTaHoBHTs 2,8. YeraosiTs ckiay ByrnesomHis i HanMmiTs HamiBcrpyKTypHi op- ys ixnix isomepis. 10*, OGuncairs Monspay Macy cymimi, mo micturs 100 ma ereny, 150 ma mponeny i 250 ma 6yreny. Yci BuMipH BUKOHAHO 3a OAHAKOBHX YMOB. Tecmosi saedanna 1. Yxaxits opmyzy 1,2-quxn0po6yt-l-eny A CH,-C=CH-CH, B CH=C-CH,-CH, ABB aa aa ION B CH,-CH-¢=CH, P CH,-CH,-CH-CH, a a Chega 2. Yxaxirs opmyzy isomepy nent-1-ery A CH,=CH-CH-CH, B CH,-CH;-CH,-C=CH ABBT CH, L L B CH;-CH,-CH,-CH,-CH; T CH;-C=C-CH; 3. Yeaxxirs bopmysy 2,3-qumerna6yr-1-eny A CH,-CH-CH-CH, B CH,-C-CH-CH, ABBT CH, H.C - CH, OOOO A B CH,=CH-CH-CH, T CH,=CH-C-CH, CH, CH, cH, 4. Yewxirs naswy pevoanun, naniserpyrrypna dbopatysia axot CH,~CH-CH=CH-CH-CH, CH, CH, A 2-mermn-4-isonponin6yt-3-en B 2,5,5-tpumerunnent-3-en ABBIT B 2,5-aumermarexc-3-en I 2-mermurent-3-en HOU 5. YVaxxirs paaox, akuii micrurs samme dbopmysu isomepis ene a A. CH;-CH-CH-CH-CH,, CH,-CH-CH,-CH,, CH,-C-C=CH CH, CH, [ B CH,-CH,-CH-CH-CH,, CH,-CH-C=CH,, CH,-C-CH=CH, CH, CH, CH, CH, B CH,-CH,-CH,~CH;-CH=CH,, CH,-CH-CH-CH-CH=CH, CH, CH, CH, T. CH,-C=C-CH,-CH,, CH,=CH-CH=CH-CH,, CH;-CH-C=C-CH, CH, 6. Yaxire Hasey pesosnun, HantiverpykrypHa dbopmysa aKol CH,-CH,-C=C-CH,-CH, H.C GH, A 1,2,3-rpueruanpon-1-ax B 3-ermn-4-merunrexc-3-c# ABBY B 1,1-nierna-2-merun6yr-1-en I 2,2-nierna-2-merm6yr-1-en [ 4l