Molecular thiab yam ntxwv mis ntawm phenol

Phenols - lub npe ntawm tus uas muaj ntxhiab alcohols. Nyob rau thaj chaw ntawm teeb meem uas tsis muaj zog acids. Ib qho tseem ceeb uas ua tau tseem ceeb ntau ntau homologues hydroxybenzene C ₆ H ₅ 0H (formula Phenol) - nyuaj tus neeg sawv cev ntawm cov chav kawm ntawv. Cia peb kawm no nyob rau hauv ntau yam.

Phenols. Cov kev mis thiab cais

Cov kev mis ntawm cov organic tshuaj ntawm muaj ntxhiab alcohols, - R-OH. Molecule nws tus kheej phenols thiab cresols tsim radical - C6H5 phenyl, uas yog ncaj qha mus txuas nrog rau ib los yog ntau hydroxyl pawg OH (hydroxyl pawg). By lawv tus xov tooj rau ib molecule phenols yog txwv kom muab zais rau hauv mono-, di- thiab polyhydric. Monohydric tebchaw ntawm no hom yog phenol thiab cresol. Feem ntau cov polyhydric hydroxybenzenes - naphthols uas muaj nyob rau hauv nws muaj pes tsawg leeg 2 fused nucleus.

Phenol - tus sawv cev ntawm uas muaj ntxhiab alcohols

Textile neeg ua hauj lwm phenol twb paub twb nyob rau hauv lub XVIII xyoo pua: lub weavers siv nws li ib tug zas xim. Nyob rau hauv lub distillation ntawm thee ib nyob rau hauv 1834 nyob rau hauv lub teb chaws Yelemees, cov chemist F. Runge tseem ceeb muaju ntawm lub substance nrog ib tug yam ntxwv qab zib tsw. Cov Latin lub npe thee - carbo, hu li ntawd compound carbolic acid (carbolic acid). German soj ntsuam ntawm muaj ua tsis tau tejyam kom paub tias cov tshuaj yeeb dej caw. Phenol Molecular mis yog tsim los pab nyob rau hauv 1842 O. Laurent, uas ntseeg carbolic derivative ntawm benzene. Rau cov tshiab acid siv lub npe "phenyl". Sharl Zherar txiav txim hais tias lub tshuaj yog dej caw, thiab hu ua nws ib tug phenol. Initial daim ntaub ntawv compound - tshuaj, tawv tanning, zus tau tej cov hluavtaws dyes. Cov yam ntxwv ntawm cov tshuaj yeeb dej caw nyob rau hauv kev saib xyuas:

• Meej pem tshuaj mis - C ₆ H ₅ OH.
• Lub molecular ceeb thawj los ntawm lub compound - thiab 94,11. e. m.
• Tas nrho cov mis ntawm lub sau ua ib pawg, - C ₆ H ₆ O.

Hluav taws xob thiab spatial qauv ntawm ib tug qauv ntawm phenol

Cyclic qauv ntawm benzene mis uas muab los ntawm German organic chemist F. Kekule nyob rau hauv 1865, thiab ua ntej nws - I. Loschmidt. Zaum muaj ib tug qauv ntawm cov organic teeb meem nyob rau hauv daim ntawv ntawm ib tug tsis tu ncua hexagon nrog alternating ib thiab ob bonds. Raws li niaj hnub tswv yim, lub uas muaj ntxhiab nplhaib - ib tug tshwj xeeb zoo ntawm yeej qauv, hu ua "conjugated daim ntawv cog lus".

Rau carbon atoms sim txheej txheem sp ² -hybridization electron orbitals. Tsis muab kev koom tes nyob rau hauv lub tsim ntawm C-C bonds ntawm lub p-electron huab sib tshooj saum toj no thiab hauv qab no lub dav hlau ntawm lub molecule tub ntxhais. Muaj ob hom electron huab uas npog tag nrho lub nplhaib. Phenol yam ntxwv mis tej zaum yuav zoo sib txawv, muab lub keeb kwm mus kom ze rau qhov kev piav qhia ntawm cov qauv ntawm cov benzene. Nyob rau hauv thiaj li yuav hais txog cov cim ntawm unsaturated uas muaj ntxhiab hydrocarbons, conventionally xam tau tias yog peb ntawm rau ob bonds uas lwm nrog peb yooj yim.

Polarization vim oxy pab pawg neeg

Nyob rau hauv qhov nyuaj uas muaj ntxhiab hydrocarbon - benzene, C ₆ H ₆ - electron huab yog symmetrical. phenol mis txawv los ntawm ib tug hydroxy pab pawg neeg. Lub xub ntiag ntawm hydroxyl lov cov symmetry uas yog reflected nyob rau hauv lub zog ntawm cov tshuaj yeeb dej caw. Cov kev sib raug zoo ntawm cov pa thiab hydrogen nyob rau hauv ib tug hydroxy pab pawg neeg - ncov qaumteb qabteb covalent. Offset ntau khub ntawm electrons mus rau lub oxygen atom ua rau ib tug tsis zoo xwb nyob saud (ib nrab). Hydrogen loses electrons thiab acquires ib tug ib nrab xwb "+". Nyob rau hauv tas li ntawd, cov pa nyob rau hauv lub O-H pab pawg neeg yog tus tswv ntawm ob unshared electron officers. Ib tug ntawm lawv attracted los ntawm lub electron huab ntawm lub uas muaj ntxhiab nplhaib. Vim li no, kev sib txuas lus yuav ntau polarized, hydrogen yooj yim hloov hlau. Cov qauv muab ib lub tswv yim ntawm cov asymmetrical xwm ntawm lub phenol molecule.

Nta cuam atoms nyob rau hauv phenol

Ib tug electron huab ntawm lub uas muaj ntxhiab nuclei nyob rau hauv phenol molecule reacts nrog ib tug hydroxyl pab pawg neeg. Nws tshwm sim phenomenon, conjugation lub npe, nyob rau hauv uas ib tug oxygen atom tus kheej khub ntawm electrons attracted rau lub hydroxy pawg ntawm ib tug benzene nplhaib system. Txo qhov tsis zoo xwb compensated los ntawm ib tug ntau dua polarization vim O-H pab pawg neeg.

Cov uas muaj ntxhiab nplhaib kuj txawv hluav taws xob faib system. Nws yog txo los ntawm cov pa roj carbon uas yog txhua yam rau oxygen, thiab yog nce ntawm ze thereto atoms nyob rau hauv lub ortho txaus (2 thiab 6). Pairing yog tsub zuj zuj xwb rau lawv "-". Ntxiv "ua haujlwm ceev - nws txav los ntawm cov atoms ntawm lub meta-txaus (3 thiab 5) rau cov nyob rau hauv lub para-txoj hauj lwm (4). phenol txoj kev tshawb no mis kom yooj yim thiab kev sib nrig sib coupling feem ntau muaj numbering ntawm lub atoms ntawm lub benzene nplhaib.

Piav phenol tshuaj zog raws li lawv hluav taws xob qauv

Dab conjugation ntawm lub uas muaj ntxhiab nplhaib thiab hydroxyl cuam tshuam rau thaj chaw ntawm ob hais thiab tag nrho cov tshuaj. Piv txwv li, ib tug siab electron ceev ntawm lub atom nyob rau hauv lub ortho thiab para txaus (2, 4, 6) ua rau cov C-H daim ntawv cog lus ntawm ib tug uas muaj ntxhiab phenol voj voog ntau reactive. Txo tsis zoo saib xyuas ntawm cov pa roj carbon atoms nyob rau hauv meta txaus (3 thiab 5). Nres ntawm electrophilic hais nyob rau hauv tshuaj tshua raug cov pa roj carbon nyob rau hauv lub ortho thiab para txaus. Lub bromination cov tshuaj tiv thaiv ntawm benzene hloov tshwm sim nyob rau hauv muaj zog cua sov thiab lub xub ntiag ntawm ib lub hauv paus. Tsim monogalogenoproizvodnoe - bromobenzene. Formula phenol tso cai tshuaj yuav hnov mob nrog bromine tshuam instantaneously tsis muaj cua sov rau cov sib tov.

Aromatic nplhaib muaj feem xyuam rau cov kev twb kev txuas polarity hydroxy pab pawg neeg, ua nws. Hydrogen yuav ntau saj zawg zog, raws li muab piv rau nyeem alcohols. Phenol reacts nrog alkalis, txoj kev ua ntsev - phenates. Ethanol tsis hnov mob nrog alkali, los yog es, cov tshuaj tiv thaiv khoom - ethanolates - decompose. Nyob rau hauv tshuaj cov ntsiab lus uas phenols - muaj zog acid tshaj alcohols.

Cov neeg sawv cev ntawm uas muaj ntxhiab alcohols chav kawm ntawv

Molecular mis homolog phenol - cresol (methylphenol hydroxytoluene) - C ₇ H ₈ O. Substance nyob rau hauv tej yam ntuj tso raw cov ntaub ntawv feem ntau nrog phenol, kuj muaj antiseptic thaj. Lwm yam homologues ntawm phenol:

• Catechol (1,2-hydroxybenzene). Tshuaj mis - C ₆ H ₄ (OH) _2.
• Resorcinol (1,3-hydroxybenzene) - C ₆ H ₄ (OH) _2.
• Pyrogallol (1,2,3-trihydroxybenzene) - C ₆ H ₃ (OH) _3.
• Naphthol. Substance Molecular mis - C ₁₀ H ₇ OH. Nws yog siv nyob rau hauv qhov siv thiab ua dyes, tshuaj, uas muaj ntxhiab tebchaw.
• Thymol (2-isopropyl-5-methylphenol). Tshuaj mis - C ₆ H ₃ CH ₃ (OH) (C ₃ H _7). Siv nyob rau hauv hluavtaws organic Science News for KIDS, thiab tshuaj.
• Vanillin tsuas yog phenolic radical muaj ib tug ether pab pawg neeg thiab ib tug aldehyde residue. Molecular mis compound - C ₈ H ₈ O _3. Vanillin yog dav siv raws li ib tug dag flavoring.

Formula reagent rau kom paub tias ntawm phenols

Zoo kev txiav txim ntawm phenol yuav nqa tawm siv bromine. Raws li ib tug tshwm sim ntawm lub hloov cov tshuaj tiv thaiv ib tug dawb precipitate tribromophenol. Catechol (1,2-hydroxybenzene) yog xim nyob rau hauv ntsuab xim nyob rau hauv lub xub ntiag ntawm yaj ferric chloride. Nrog tib reagent reacts phenol thiab ib tug triphenol yog tsim muaj ib tug violet xim. Zoo tshuaj tiv thaiv rau resorcinol - tsos tsaus nti violet xim nyob rau hauv lub xub ntiag ntawm ferric chloride. Maj mam, cov xim ntawm cov tshuaj puv dub. Cov mis ntawm lub reagent, uas yog siv kom paub txog tej yam phenol thiab nws homologs, - FeCl ₃ (ferric chloride (III)).

Hydroxybenzene, naphthol, thymol - tag nrho cov phenols. Cov kev mis ntawm lub substance los mus txiav txim tus mej zeej hauv cov tebchaw mus rau lub uas muaj ntxhiab series. Tag nrho cov organic tebchaw uas muaj nyob rau hauv lawv cov mis phenyl radical C ₆ H _5, uas cov hydroxy pawg neeg ncaj qha mus txuas kom muaj khoom tshwj xeeb. Lawv txawv los ntawm dej cawv yog zoo tshaj plaws qhia acidic xwm. Piv nrog rau tshuaj homologous series benzene, phenols - ntau yam tshuaj compound.