Zoo kev ntsuam xyuas rau phenol. Kev npaj ntawm Phenols: Cov tshuaj tiv thaiv

Carbolic acid - ib tug ntawm cov npe Phenol, cim tias seb thaum nws tshwj xeeb coj cwj pwm nyob rau hauv cov tshuaj dab. Qhov no cov ntaub ntawv uas yog yooj yim dua benzene nkag mus rau hauv nucleophilic hloov cov tshuaj tiv thaiv. Lub xam qhovkev thaj chaw ntawm ib tug compound yog piav muaj acidic hydrogen atom nyob rau hauv lub hydroxyl pab pawg neeg sib raug zoo rau lub nplhaib. Txoj kev tshawb no ntawm molecular qauv thiab high-zoo lus teb rau pub tus phenol compound xws li uas muaj ntxhiab tebchaw - benzene derivatives.

Phenol (hydroxybenzene)

Nyob rau hauv 1834, ib tug German chemist Runge faib carbolic acid los ntawm thee ib, tab sis yog tsis tau decrypt nws muaj pes tsawg leeg. Tom qab ntawd, lwm yam kev soj ntsuam tau npaj ib lub mis, thiab nqa ib tug tshiab kev twb kev txuas mus rau lub uas muaj ntxhiab haus dej cawv. Qhov yooj yim tus neeg sawv cev ntawm no pab pawg neeg - phenol (hydroxybenzene). Nyob rau hauv nws cov ntshiab daim ntawv, qhov no tshuaj yog ib tug pob tshab siv lead ua muaj ib tug yam ntxwv tsw. Cua phenol xim tej zaum yuav hloov los ua liab los yog liab. Rau uas muaj ntxhiab cawv raug txom nyem dej txias solubility thiab zoo - nyob rau hauv cov organic solvents. Phenol melts ntawm ib tug kub ntawm 43 ° C. Yog ib tug tshuaj lom compound, nyob rau hauv kev sib cuag nrog cov tawv nqaij ua mob loj heev kev kub nyhiab. Cov uas muaj ntxhiab moiety yog ib tug tshaj dhau ntawm phenyl (C6H5-). Ncaj qha nrog ib tug ntawm cov pa roj carbon atoms ntawm cov pa yog sib raug zoo nrog ib tug hydroxyl pab pawg neeg (-OH). Lub xub ntiag ntawm txhua tus hais qhia tau hais tias tsim nyog zoo tshuaj tiv thaiv rau phenol. Cov mis uas qhia tag nrho cov ntsiab lus ntawm atoms ntawm tshuaj ntsiab nyob rau hauv lub molecule - C6H6O. Qauv muaj kev cuam tshuam tus yam ntxwv mis, xws li cov voj voog thiab Kekule haumxeeb pab pawg neeg - hydroxyl. Nrig txog kev pom cov sawv cev ntawm cov molecule, ib tug uas muaj ntxhiab cawv muab sharosterzhnevye qauv.

Nta ntawm lub molecular qauv

Cuam ntawm lub benzene nplhaib thiab OH pab pawg neeg txhais tshuaj cov tshuaj tiv thaiv ntawm phenol nrog co, halogens, lwm yam. Thaum ua txhua yam rau lub uas muaj ntxhiab lub nplhaib ntawm cov pa atom ua rau ib tug redistribution ntawm electron ceev nyob rau hauv lub molecule. Kev sib txuas lus O-H yog ntau ncov qaumteb qabteb, uas tau nyob rau hauv ntau zog muaj ntawm lub hydrogen nyob rau hauv lub hydroxyl pab pawg neeg. Lub proton yuav hloov los ntawm hlau atoms, uas qhia hais tias tus acidity ntawm cov phenol. Nyob rau hauv lem, tus OH pab pawg neeg tsub kom lub reactive thaj chaw ntawm lub benzene nplhaib. Delocalization ntawm electrons nce, thiab muaj peev xwm electrophilic hloov nyob rau hauv lub nucleus. Qhov no yuav tsub lub muaj ntawm lub hydrogen atoms sib raug zoo rau cov pa roj carbon nyob rau ortho- thiab para-txoj hauj lwm (2, 4, 6). Cov nyhuv no yog vim lub xub ntiag ntawm lub pub electron ceev - hydroxyl pab pawg neeg. Vim nws cov cawv phenol active tshaj benzene behaves nyob rau hauv tshua muaj tej yam tshuaj thiab tshiab substituents taw qhia kom paub nyob rau hauv lub ortho- thiab para-txaus.

Lub acidic zog

Lub hydroxyl pab pawg neeg ntawm cov uas muaj ntxhiab cawv cov pa atom acquires ib tug zoo xwb, weakening nws sib txuas lus nrog hydrogen. proton tso tawm yog thawm, li ntawd, phenol behaves raws li ib tug tsis muaj zog acid, tab sis tus muaj zog dua alcohols. Zoo tshuaj tiv thaiv rau phenol muaj xws li kuaj litmus xeem nyob rau hauv lub xub ntiag ntawm protons hloov xim los ntawm cov kob xiav mus liab. Lub xub ntiag ntawm halogen atoms los yog nitro pawg uas txuam nrog lub benzene nplhaib ua rau ib qho kev nce nyob rau hauv lub hydrogen kev ua si. Cov nyhuv yog pom nyob rau hauv nitro phenol molecules. Lower acidity substituents xws li ib tug amino pab pawg neeg, thiab alkyl (CH3-, C2H5-, etc.). Tebchaw uas theem ua ke ib benzene nplhaib, ib tug hydroxyl pab pawg neeg thiab ib tug methyl radical, yog hais txog cresol. Nws cov khoom yog weaker dua carbolic acid.

phenol tshuaj tiv thaiv uas sodium thiab alkaline

Ib yam li ntawd acids phenol yog reacted nrog hlau. Piv txwv li, reacts nrog sodium: 2C6H5-OH + 2Na = 2C6H5-ONa + H2 ↑. Tsim sodium phenoxide, thiab gaseous hydrogen yog tso tawm. Phenol yog reacted nrog soluble bases. Nws tshwm sim neutralization cov tshuaj tiv thaiv tsim tau ib cov ntsev thiab dej: C6H5-OH + NaOH = C6H5 -ONa + H2O. Muaj peev xwm muab hydrogen nyob rau hauv lub hydroxyl pab pawg neeg nyob rau hauv lub phenol yog qis tshaj feem ntau inorganic thiab carboxylic acids. Nws displaces nws los ntawm cov ntsev yaj nyob rau hauv cov dej txawm carbon dioxide (carbonic acid). Cov tshuaj tiv thaiv kab zauv: C6H5-ONa + CO2 + H2O = C6H5-OH + NaHCO3.

Lub tshua ntawm lub benzene nplhaib

Aromatic zog yog vim electron delocalization nyob rau hauv lub benzene nucleus. Hydrogen los ntawm lub nplhaib yog pawg los ntawm halogen atoms, nitro. Ib tug zoo xws li cov txheej txheem nyob rau hauv phenol molecule yog yooj yim dua hais tias ntawm benzene. Ib tug piv txwv - tus bromination. Benzene halogen ua hauj lwm nyob rau hauv lub xub ntiag ntawm catalyst, tau bromobenzene. Phenol yog reacted nrog bromine dej nyob rau hauv ib txwm tej yam kev mob. Lub sis ntawm ib tug dawb precipitate ntawm 2,4,6-tribromophenol, uas nws tsos paub qhov txawv cov xeem tshuaj uas zoo sib xws rau nws los ntawm uas muaj ntxhiab tebchaw. Bromination - zoo tshuaj tiv thaiv rau phenol. Kab zauv: C6H5-OH + 3Br2 = C6H2Br3 + HBr. Qhov thib ob cov tshuaj tiv thaiv khoom - hydrogen bromide. Thaum reacting phenol nrog nta nitric acid tau nitro derivative. Cov tshuaj tiv thaiv cov khoom nrog ib tug concentrated nitric acid - 2,4,6-trinitrophenol los yog picric acid muaj zoo tswv yim tseem ceeb.

Zoo kev ntsuam xyuas rau phenol. daim ntawv teev

Nyob rau hauv lub sis ntawm tshuaj tau tej yam khoom noj uas tso cai rau koj mus muab cov zoo muaj pes tsawg leeg ntawm lub starting cov ntaub ntawv. Ib tug xov tooj ntawm cov xim cov tshuaj tiv thaiv qhia lub xub ntiag ntawm hais, tej pawg neeg uas yog cov pab tshuaj ntsuam xyuas. Zoo tshuaj tiv thaiv los ua pov thawj rau hauv lub hav zoov ntawm phenol ib molecule ntawm tshuaj lub uas muaj ntxhiab nplhaib thiab OH-pawg:

1. Cov tshuaj ntawm phenol xiav litmus ntawv liab.
2. Dawb lias tshuaj tiv thaiv phenols kuj ua nyob rau hauv ib tug tsis muaj zog yooj yim nruab nrab nrog diazonium ntsev. Ib tug daj los yog txiv kab ntxwv azo dyes.
3. Yog reacted nrog bromine dej xim av precipitate tshwm dawb tribromophenol.
4. Nyob rau hauv cov tshuaj tiv thaiv nrog ferric chloride tshuaj tau phenoxide ferric - tshuaj xiav, violet los yog ntsuab coloration.

Tau phenols

Phenol Qhuav nyob rau hauv qhov kev lag luam yog nyob rau hauv ob los yog peb theem. Nyob rau hauv thawj theem ntawm lub propylene thiab benzene nyob rau hauv lub xub ntiag ntawm txhuas chloride ua cumene (isopropylbenzene lub npe). Cov kab zauv ntawm cov tshuaj tiv thaiv ntawm Friedel-Crafts cov tshuaj tiv thaiv: C6H5-OH + C3H6 = C9H12 (cumene). Benzene thiab propylene nyob rau hauv ib qho ratio ntawm 3: 1 yog hla dhau ib tug acidic catalyst. Qhia, es tsis txhob rau ntawm cov tsoos catalyst - txhuas chloride - ecologically ntshiab zeolites. Thaum lub theem kawg ntawm lub oxidation yog ua nrog cov pa nyob rau hauv lub xub ntiag ntawm sulfuric acid: C6H5-C3H7 + O2 = C6H5-OH + C3H6O. Cov phenols tej zaum yuav muab tau los ntawm distillation ntawm thee, yog intermediates nyob rau hauv qhuav ntawm lwm yam organic tshuaj.

Kev siv cov phenols

Aromatic alcohols yog lug siv nyob rau hauv lub yas kev lag luam, dyes, tshuaj tua kab, thiab lwm yam. carbolic acid ntau lawm ntawm benzene yog thawj kauj ruam nyob rau hauv cov creation ntawm ib tug xov tooj ntawm polymers, xws li polycarbonates. Phenol yog reacted nrog formaldehyde, phenol-formaldehyde resins yog tau.

Cyclohexanol yog lub raw khoom rau zus tau tej cov polyamides. Phenols yog siv raws li antiseptics thiab disinfectants nyob rau hauv deodorants, muab tshuaj pleev. Siv kom tau phenacetin, salicylic acid thiab lwm yam tshuaj. Phenols yog siv nyob rau hauv qhuav ntawm resins uas yog siv nyob rau hauv hluav taws xob khoom (keyboards, nyob). Lawv kuj siv nyob rau hauv qhov kev npaj ntawm azo dyes, xws li phenylamine (aniline). Picric acid, uas yog lub nitro derivatives ntawm phenol siv rau uas tseg tau ntaub so ntswg, explosives siv thiab ua.