KHOA CHUYEN DE LIVEVIP HOA 11| TYHH \v LY THUYET TRONG TAM PHENOL HOA HOC (Slidenote dénh riéng cho LOVEVIP - Thay Ngoc Anh TYHH) KIEN THUC CAN NHO: nigm Phenol 1a abiing hop chat hivu co trong phin ti cé nhém — OF lién két true tiép véi nguyén ti carbon cia vong benzene. 7 or (es) phenol 3-methylphenol a ¢ cH fot Se rH “ 7 chy 2-methylphenol 4-methylphenol Cth Gly -ott CH. Gfig-ont + Pha bik _— pha oft ~ © trong very benne, oa XS oy \ abode tid, - of — Cano), gene vary ben ene (-a-o11 | Relig 7 PRone cin ksi C mono phend,) Song, Sher \ PRenck, ca, Rat’ Col phenol) 10 ~LOy- crt + Powks php = Np A cael ahr 15 A nhars TRE pRonshe Don Bo tid CS txy vorg bentene pF CL nig pont &, el pa o- creak, t % ire Cres, Tinh chat vit Nenen > Nensorr - O diéu kién thuong: phenol la chat ran, khong mau, a6ng chay & 43 °C, s6i & 181.8 °C. > son ~ Phenol trong mage 6 dién kién thing. tan nhiéu khi dun néng: tan t6t trong cée dung méi hi conhu: ethanol, ethér Va acetone. ~ Phenol dic va cé thé gay bong Ichi tiép xtic véi da nén phai can théa ki sé dung.! Lal 5 -o+ @ # oy 1 ro — Sg mat Be coo fen) = 9 4) ay] 9% / HOD &qtegre Pt Gitisy O Cteon > TEED, > Geltsor > Hogy + GrsoHy 180 7 Cheon ‘Trong phan ti phenol, do anh huéng cua véng benzene nén lién két O — H cia phenol phin cuc manh hon so v6i alcohol, vi vay phenol thé hién tinh acid yéu. Neodi ra, do c6 vong benzene,pén phenol c6 thd tham gia phin img thé nguyén tr hydrogen cba vang (ey < pot < © benzene, Tinh chat héa hoc a) Phan im; thé én tir H cia nhém — (tinh acid ciia phenol) ene Dri ct ay go & ; oy CaOH +150 —= CHO-HHO'CIN: «= GTTsoN = Gite” + TE ——> tho Phenol 1a mét acid véu, dung dich phenol khéng lam 48i mau qui tim =< TLQ Phenol cé thé phan img duoc vdi kim loai kiém, dung dich base, muéi sodium carbonate - Vide: CaHs0H+ NOH —> CaHsONa+ HO Cth aad) ke Trong dung dich nude, phenol phan li theo cén bang sau: Ke CsHs0H + NaxCO3 —— CeHsONa + NaHCO3 + RAY LO, > GOH > Hae 4 _ id Hh Hoy nt cg Q+ ho + Grove —> Gitson + a) 11%, -_ on + Ne fe —» —0Na + dn Chenhe; allco fob) One. B) Phan ting thé 6 vong thom = Do aah huéng cia ahém — OH, phan Gng thé nguyéa ti hydrogen 6 vang benzene cua phenol xay ra dé dang hon so véi benzene. - Phenol cé thé tham gia phan tg thé nguyén ni hydrogen cua vong benzene. Phan tng thé uu tién vao vi tri 2, 4 va 6 (ortho va para).' f -Vidu: AS Gr + @ a oH oH Br Br ¥ +3Brn—> a +3HBr —> axich DI jhensh 7 @&® Ss 28) a7 Ne 's <— syF iO, Esa? 2) (pieric acid) + 3120 HN, 445 ~ I toplanl Ung dung — Diéu ché @) Uing dung 5) Diéu ché- Phenol due ting hop tir cumene (isopropylbenzene). Ngoai ra, phenol con duoc diéu ché tir nhwa than a ad GN) ai a oy fol 2) + oresca a) C2 ca BAI TAP AP DUNG: ‘Xée nhdn dting hodc sai cho cdc phat biéu vé dac diém va tinh chat cia phenol 1 | Phenol c6 nhém chiéc -OH lién két truc tiép véi aguyén tir carbon no. Ss 2 | Phenol don gian ahat cé chia I nguyéa ti oxygea._(Giizor S SIN FS khdng phi 18 alcohol. ’ ys 32 vatoluene (M=92) 66 ahiét 6 néng hay twong Goong | nhau do khoi luong phén/té gan bing hau, 2 ple 3 BHD 5 | Phenol to Give itn kéthydronpyveiaute. GI. g=H D 6 | Phenol cé tinh acid lam quy tim hoa go. nam T 3 7 | Phenol tham gia phan ing Seve Br tao thank 2.4,6 tribromophenol. s Hay xéc dink céng thiic cdu tao ca hop chit hitu co X, biét X cé céng thie phan ti C7Hs0, 6 chia ‘vong benzene va phan tmg duoc véi dung dich NaOH. orp] Kkete a ot on- oct OF pe pan < Ot- x Oa @ , abo hoe Oils - me +O 04. Hop chat hitu co X thude loai phenol, c6 cing thc phan ti 1a Cetin 8 dng phin céu tao cia X 1a bao nhiéu? 4) oH K=4 = Cr Rati * ‘py 4 ee K ox @ .° @ 3ox.,9 ¥ t ot ft oo oH ts on en a, Joy % ver “Oy Oo ct, en eg Woe BR “4 Cho céc chit c6 cng thitc sau: CéHsOH, CeHsCHs, CoHsCD va caéc gia tri nhiét d6 s6i (khong theo thi tu) 1a 110°C, 132°C, 182 “cf dy dodn nhiét 46 séi tuong tng véi méi chat tréa. Gidi thich.ag @ So sanh nhiét dé néng chay cia 3 chat phenol, hydroquinone (4-hydroxyphenol) va resorcinol (3- hhydroxyphenol). Giai thich. On (phen), aoa * cwydcoqunons; a | (resorcinel) 214 fo) 0-6 5-0-0-6- o nS Ww Trong phan ti phenol cé sv anh hueng qua lai gitia nhém—OH va géc ~Célls/ gc Calis lim tinh acid ca phenol manh hon so véi alcohol va nhém -OH lam cho phan tg thé nguyéa ti hydrogen cia vong benzene dé dang hon so v6i benzene/Hay viét cdc phwong trinh phan mg minh hoa nhén dink trén —Twh acid: Catson r Natt > — Gilsae + + Naat Gricona me by plaka’ oO + ay! & * sh > fies 42 Thc hign cdc thi nghiém sau: a NaOH_ co, Ad —chopheaot io ngughe him uve ved ag uci hy ong dich cé mau trang duc (Hinh A). - Cho dung dich NaOH vao éng nghiém thay dung dich chuyén sang trong suét (Hinh B) ~ Suc khi COp vao éng nghiém thdy dung dich chuyén mau tring duc nhy ban diu (Hinh C). Giai thich hign twong trong céc thi nghiém trén va viét cdc phurong trinh hod hoe. ~ Khi cho phenol véo éng nghiém A, do phenol tan kkém trong aude néa dang dich 66 miu tring duc (dung dich phenol bao hoa). - Cho dung dich NaOH vao éng nghiém thay dung dich chuyén trong suét do phan tng cia phenol véi ‘NaOH tao muéi tan: oO So di wen phombste. (CéHsOH + NaOH —+ CellsONa + H2O ‘ar - Khi suc khi CO2 vao éng nghiém, CO; phan tng véi phenolate tao thanh phenol: (CéHsONa + CO2 + HO —> C6HsOH + NaHCOs, Voy duecin) Cho hep chat hitu co cé céng thite cau tao sau: Oa ont. ‘Viet phuong tinh hod hoc cla phan tng gilra hop chat nay véi cac chat sau: a) Na; ) Dung dich NaOH: c) Dung dich NaxCOs: 4) Dung dich bromine. a) 4+2Na ——> +E >) +NaOH —> +o °) + NaxCO; —> + NaHCOs HOH,C: oe +2Bn —> + 2HBr a) So sinh diéu kién phan ng brominc hod vio vong benzene ca phenol va benzene, Ti 46, rit ranhén ‘xét kha nang thé nguyén tiy hydrogen ciia vong benzene ciia phenol so véi benzene. +) Vig phyong trinh hod hoc ca phan tng xy ra khi cho 4methylphenol téc dung véi nvdc bromine. a) Benzene phan tng voi Br; 6 diéu kién nhiét d6 cao va c6 xic tac muéi iron(II]) halide. ' (ec6,) Bi +B EN + Phenol dé dang phan tmg véi Br 6 diéu kién thong. 6 oY br +3HBr — Kha ning thé nguyén ti hydrogen 6 véng benzene cia phenol xay ra dé dang hon véi benzene. oY Hs + 2B —> Hs + HBrCan (02) Picric acid cé nhiéu ing dung trong y hoc (dinh long creatinine dé chan dodn va theo di tinh trang suy than: khirtring va lam kho da ki diéu tri béng,...)f trong quan su (sin3 phong thi aghiém (nhuém mau, lam thuéc the.._.). a) Viét phyong trinh hod hoc cua phan img diéu ché picric acid tir phenol. ) Giai thich vi sao trong phong thi nghiém thwong bao quan picric acid trong lo duéi mét lép nuse va trong qua trinh lam vide véi picric acid, (rdah 48 acid tiép xiic véi kim loai? ) @® oH ON. : NO: a) S +3HONO? > Nop (picric acid) + 3EO b) Phan to picric acid dé aay ch4y, nd manh nén 4é an toan, thwéng bao quan picric acid trong lo duéi “~) mét Ip nse. Mat khéc, picric acid c6 tinh acid manh, phan ting v6i kim loai toa nhiét, tao musi picrare cing dé gay chay né. ca ‘Trong v6 qua cay vanilla cé hop chat mii thom dé chiu, tén thvong 1a vanillin/Ceng ‘thie cau tao cia ae vanillin a € +tho HO Naot 7 > cr, + Na 6 zy Nlo- GH HO cH oct, iH a) Viet cng thie phan tis cia vanillin. Cy Tl 6, §) Du dodn kha ang tan trong nuse/ trong ethanol/ra tong dang dich kiém nr NaOH, KOH/cia vanillin Kho de f c) Mau vanillin da tigu chuén ding trong céng nghiép san xudt duoc phdm va thyc phdm cén cé trén 99% vé khéi luong 14 vanillin/Dé inh lvong mét miu vanillin, ngwdi ta lim ahu sau: Hoa tan 0.120 gam mau trong 20 mL ethanol 96% va thém 60 mL nude cat, thu duoc dung sic ide X phaa ing ‘vita dit véi 7,82 ml. dung dich NaOH ning d6 0.1 M va tap chat trong mau khéng phan ing véi NaOH. ‘Miu vanillin trén cé di tiéu chuan ding trong céng nghiép san xuat duoc pham va thuc pham khéng?Dep PRO P94 52 Brvobabh = — Ge AO = $4 0SZ,2 2 : CivG2) Cé ba éng nghiém chia céc chit ling sau: dung dich propanol. dung dich phenol va bendene. Hay 48 xudt mét thuéc thi dé aban biét dng nghiém chia dung dich phenol. dB CKD) Cho biét 6 didn kién nhiét 46 va dp sudt cao, xay ra phan tng thé nguyén te halogen (in két true tiép v6i véag benzene) bang ahém ro) a) Viét phuong tinh hod hoc cia phan tng xéy ra khi dun néng hén _: chlorobenzene va dung dich NaOH ac, de 6 nhiét 44 300 °C, dp swat 200 bar. co (nor a canting b) Lap so 48 didu ché phenol tir benzene va cdc chit vd co. a Ee” > oO up c) Tinh kchdi long benzene can thiét dé diéu ché duoc 9.4 ke phenol theo so dé & phan b), biét hiéu suat cia cd qué triah, (2 y et + Nor Chor + Nae = (> Ome + tho Gtse + Neo 5 GtsoNa # iO «Na SA 78, A = “ y ate = Wa. gut StL QP = 4g sry to- Gt, Cio, ) a) Picrie acid (2,4,6.trinitrophenoly trude day duge sit dung lam thude a6/pi tdng hop picrie acid, agudi ta cho 47 gam phenol phan tng véi hon hop HNO} dac/H)SO, dac, du. Tinh khdi luong picric acid thu duoc, biéthigu sudt phan ig 14 63% mm = ‘tt. Rowe = gg eg. FSS = F2,435g~ can 5) Trong thi nghiém cia phenol véi nde Br, thu duoc san phim hiw co 2,4,6-tribromophenol (két tia mau tring) dat gan 100% va khéng thu diroc cdc san phém thé bromo khac & cdc vi tri cdn lai cia phenol. Giai thich.c ne) ‘Trong céng nghiép, ngodi phwong phap diéu ché phenol ti cumene hod tiv nhva than 44, ngudi ta cén thuc hién diéu ché bang phan tng thuy phn din xuat chlorobenzene véi dung dich NaOH dac, énhiét 4§ 350°C, ap suat cao (quy trink Dow), sin phim hitu co la muéi sodium phenolate, acid hod bing dung dich HCI, thu duoc phenol. 2) Viét phuong trinh hod hoc cba céc phin éng xiy ra tO” + IQ —7 Gtiso#e Nace ») Tai sao khi thhuy phan chlorobenzene khéng tao than sin phdm truc tiép phenol, ma tao than sodium phenolate? § (Gyan + Natt ~—> (O>oNw + fto Thi wudng tiéu thy phenol trén toan thé gidi khoang 11,37 wieu tan tong nam 202g du kién sé tang len 14.07 trigu tén véo nim 2029/Phenol duge sit dung 4é san xudt nhiéu loai hod chit nhu bisphenol A, nwa phenolformaldehyde, picric acid va cdc chat ede! Khoan; 0%) lwong phenol duoc san xudt tir cumene (bing phuong phap cumene, chu trinh cumene,.)/Bé cung cap di sin lugng tiés thy cia phenol trong nam 2021, khéi lvgng cumene da ding dé san xuit phenol 1A bao shiéu7/(Chi tinh trén hrong phenol da tiéu thu, khong bao gém lvong cumene thuc té san xudt phenol chua tiéu thy). cach wn 2 Ast yt AEB. 0 = Io6 a+ ” cunen ca® Chit nao sau day cé nhiét 46 si cao nhat? A. Chloroethane. B. Methanol. C. Ethanol. Prrenot Ca(1D)_ Phenol va ethanol déu phan ing duve vi Qya B, dung dich NaOH CC. dung dich bromine loing. D. dung dich NaxCOs. ca ‘Dan xuat halogen nao sau day khi tac dung voi NaOH khéng tao thanh alcohol? JX CoHSCH:Br. Crasc. JX CHsCHB)CHscinG) Cho hai phan tng sau: (1) C6HsOH + NaxCO3 —> CeHsONa + NaHiCOs (2) C6HsONa + CO + Hai phan img wen ching té phenol YG 18 mét acid ment JK la mét base manh, ‘9 cé tinh acid manh hon née 1 ciaHaCOs. (BD) cé tinh acid manh hon nic 2 cba HxCOs Can(SB)_Khii nhs tr tx dung dich bromine vao éng nghiém chita dung dich phenol, hién trong quan sat durac trong éng nghiém 1 @nawse brom bi mat mau va xuit hién két tia tring, B. dung dich trong sudt C. xudt hién két via wang. D. khéng xay ra hién twong gi Cin G3) Cho vai giot mde bromine vao dung dich phenol, lic nhe thay xudt hién Dkét tia tring B. két tia dé niu C. bot Ki D. dd mau xanh Phin tmg véi chdt/dung dich no sau day cia phenol chtimg minh phenol cé tinh acid? ANa, (Byung dich NaOH. C. Dung dich bromine. D. HNOs éac/H2SOs dae. Can (3) Liéu twong duoc tinh todn phis hop cita mét sé hop chét phenol nh: 4-hexyiresorcinol duce diing trong thvdc gidm ho, chit tri ném; butyl paraben (HOCesCOO[CH2];CH:), BHA, BHT, duye tng dung lam chit bao quan trong ché bién thyc pham, mi pham, duge phdy/* ‘Vi dic diém ctia cdc hop chat nay 14 G. 06 hoat tinh sinh hoc. B. chi phi thép. C. dé bao quan. D. khong gay déc néu ding du liéu lvong. Cé ba dng nghiém (1), (2), (3) clita riéng biét ba hod chit sau: ethanol, glycerol, phenol (khéng theo ‘thé ty). Mét hoc sinh tiga hanh thi aghiém 4é ahén biét céc chat trén, tha duoc két qua nhw 6 bang sau day. bag bd moO Tan tot, qt Tan tot tieme Baad tinal Khong 6 ‘hién tuong gi T . ‘Khéng cé hién tuong Dung dich bromine Ké tie tring . xay ra gixay ra Ca(OH) Tao phic xanh lam dim | Khéng tao phic Khéng tao phic ‘Tho ty hod chat trong cdc Ong aghiém (1), (2), G) lan luot la A. ethanol, glycerol, phenol. B. glycerol, ethanol, phenol. etyecrol, phenol, ethanol D. phenol, glycerol, ethanol.Cin) Hop chat hitu co X (phan 13 c6 vOng benzene) cé céng thie phi ti 1a C7HsO2, téc dung due w5i Na va voi NaOH/Biét rang khi cho X téc dung véi Nea) 36 mol Hz thu dugc bing 36 mol X tham gia phan ‘ing va X chi tac dung dvgc v6i NaOH theo ti 16 s6 mol 1: 1/Céng thie céu tgo thu gon cla Xi >X CaHsCHOH @yocancrnon &RCHCHOHp. DK CHOCO. Ws ay > XoF V1 aE > oH iF dota, cia) Sé dng phin chia vong benzene, cé céng thie phin ti C7H,O, phan tmg duoc v6(Na ©. HH pa A3. B. 5. Ch Chott oY “@ CO) ® D) Cho céc chat c6 cing céng thie phin ti cA on XK Ae LU UW 86 chét via phin tg dugc v6i Na via phin img duoc véi dung dich NaOH 1a OF1—p Al B.2 © D.4. Cau @®. Cho céc chit: C3HsOH, C3HsBr, CéHsOH, CeHsCH;OH, CaHsCl. $6 chit téc dung duoc véi dung dich ‘NaOH lodng khi dun néng 1a Ad. B.S. c3. @): CivG@D Phat bigu ado sau day khong ding? “A. Alcohol va phenol déu tham gia phan tig voi Na V B. Cho phenol phn ig véi dung dich NaOH, sau dé nhd vai giot HCI vao dung dich thi lai thu dugc phenol Greona OG rteort te Y ©. Alcohol da clic cé nhém —OH Ldn ké phan tg duge véi Cu(OH)>, cn alcohol don chite thi khéng phan ing. @)Dua néng alcohol vi HySO, ic chi thu duoc alkene. / oe, cav@) Cho céc phat bidu sau vé phenol: @)Phenol cé nhiét 48 sdi cao hon ethanol. @)Phenol téc dung duoc véi dung dich NaOH. ©Phenol téc dung duoc véi dung dich Na:COs@ Phan ing thé vao yng thom cia phenol dé hon thé vao ving benzene. Trong s6 cac phat biéu trén, 36 phat biéa ding la AL B.D, c3. Civ Cho céc phat bide sav: @trong phéa ti alcohol cd nhom -OH. (toys alcohol dé tan trong nude vi phan ti alcohol phan cyc va alcohol cé thé tao ién két hydrogen v6i phan ti nwéc. ‘6 Hop chit CcH;OH 1A alcohol im, don che. (@Nhiet 46 s6i cia CHsCH:CELOH cao hon ciia CH}OCH2CEB. GXCo 5 alcohol ééng phin céu tao img vi céng thitc phin ti CHO. Cygor} Sé phat bidu ding 1a coy tty AD B.S D3 4 © 'C) Cho céc phat biéu sau vé phenol: (@Phenol tan mét phan trong nude 6 diéu kién thudng. ® Phenol tan v6 han trong aude 6 diév kién thudag, @) Phenol tan tét trong nude khi dun nong @ Nhiét 46 néng chay cia phenol cao hon ethanol. OPrenol cé tinh dc va cé thé gay béng khi tiép xtc v6i danén cda phai can than khi si dung. 'S6 phat biéu dung 1a A2 B3 a D.5 ctor Cau@Bt_ Cho cée phat bidu sau vé phenol (C08): a aati OH we NS & Phenol la hop chét hit co trong phan ti cé vang be b) Do cé nhém —OH nén phenol fam\@iian trong née & diéu kién thuong trong ty ethanol. @Dung dich phenol khéng lim 4éi mau gidy quy tim, do dé phenol cé tinh acid yéu. @)Phenol phan tng duoc véi dung dich NaOH. @Phenol phan tg duoc voi NarCOs do 6 tinh acid manh hon nac 2 cia carbonic acid. @Phenol dé tham gia phan tng thé bromine va thé nitro hon benzene do anh hvéng cia nhém —OH. Sé6 phat bidu ding 1a ee AD B.S. ©: D.5. TRI TUE TOA SANG —— (Thay Ngoc Anh | TYHH) ————