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Nm c nh ngha, phn loi v danhphp ca phenol

Trnh by

c cc tnh cht l h

c, hahc ca phenol

ng dng v ngha ca phenoltrong isng cng nh trong yhc.

MC TIU

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4

Phenol c pht hin vo nm 1834, khi n c chit xut t

nha than , vn l ngun chnh cho n khi s pht trin cangnh cng nghip ha du. Cc cht st trng c tnh ca phenolc s dng bi Sir Joseph Lister (1827-1912) trong k thut

phu thut tin phong ca ng v cht kh trng.

Phenol cng l thnh phn chnh ca khi carbolic Ball , mtthit b trn th trng ti London vo th k 19 nh l bo vngi s dng chng li bnh cm v cc bnh khc.

c bit, phenol c s dng nh mt phng tin git ngica c quc x trong th chin th hai bi n to ci cht mdu, nhanh chng, hn na gi thnh r. Phenoltr thnh c ttim c la chn thng qua nhng ngy cui cng ca cucchin. Pht xt c tim cho hng ngn nn nhn

ti Auschwitz-Birkenau, khong 1 gram l git cht mingi. Ban u, tim phenol vo cnh tay, sau chuyn sangtim trc tip vo tim nn nhn cht nhanh hn do c tnh cca loi hp cht ny.

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Phenol l dn xut ca hydrocarbon thm dos thay th mt hay nhiu nguyn t H cavng benzen bng nhm OH.

V d:

Phenol - naphtol

-Nu phn t Phenol

c 1 nhmOH, ta cmonophenol

-Nu phn t cnhiu nhm OH,ta c polyphenol

(Resorcinol)

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Nhm OH gy ra hiung +C lm cho phnt phenol c mts tnh chtcbit sau:

- Tngmtelectron cc v tr o-,p-tng kh nng tham giaphnngth

- di lin kt O-H > O-H ca alcol,

lm tng tnh acid- Lin kt C-O phenol rtbn, dilin kt C-O < C-O ca alcol.

II. cimcutrc,ng phn v danh phpc im cu trc:

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Cc hp cht phenol l ng phn do v tr canhm chc v nhm th

-V d nh vihydroquinon, c 3

ng phn do v trca nhm chc

-Hay vi hp cht

cresol cng c 3ng phn do v trtng i gia nhmchc v nhm th

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Quy tc chung:

Tn Hydrocarbon + s chv tr ca nhm OH + ui ol

a. Danh php IUPAC:

Benzen-1,2,4-triol

OH

OH

Naphtalen-1,3,7-triol

b. Danh php thng thng:Mt s phenol c tn thng thng, v d nh:

Phenol m-cresol p-hydroquinon

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- Phenol l chtrnkt tinh,khng mu, db oxy hatrong khng kh thnh mu hngnht, tnc=43oC.

tnc(oC)

ts(oC)

45,7

214,5

97

216

115

279

- Do c lin kt H ni phn t nn ng phn ortho canitrophenol c t0s, t

0ncthp hn ng phn meta v para

III.Tnh chtvt l

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III.Tnh chtvt l

- lu trong khng kh, phenol tchyra.

- Phenol c, c tnh st trng, lmbng da.

- Tuy c khnng to lk H vincnhngphenol t tan trong nclnh (9,5g/100g nc25oC). Khi un nng, tan tng ln, 70oC

phenol tan v hn trong nc.

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III.Tnh cht l hc:

Phenol t tan trong nc

lnh

nhng tan nhiu trong ether v

benzen

Ti sao???Do phn t cha vng benzen v lin kt O-Hphn cc mnh nn c th to lin kt hydrotng i bn vng. Tuy c khnng to linkt hydro vi nc nhng phenol t tan trongnc v c gc thm cng knh trong phn t

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Phenol (v

cyclohexanol)

Cng thc TncoC tsoC tan :g/100g H2O

pKa25oC

Phenolo-cresol

m-cresol

p-cresol

resorcinol

hydroquinolpyrogalol

1-naphtol

cyclohexanol

C6H5OHo-CH3C6H4OH

m-CH3C6H4OH

p-CH3C6H4OH

1,3-C6H4(OH)2

1,4-C6H4(OH)21,2,3-C6H3(OH)3

1-C10H7OH

C6H11OH

4330

12

36

110

171134

96

26

182192

203

203

277

286309

288

161

9,52,5

2,6

2,3

229

6,062,5

0,0

3,6

10,010,2

10,0

10,2

9,4

10,07,0

8,0

18

III.Tnh chtvt l

Hngsvt l camts phenol

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IV.Tnh cht ha hc

*Phnngca nhm OH

1. Tnh acid

- Phenol c tnh acid mnhhn alcol nhngyuhn acid carboxylic.

- Do hiungC ca vng benzen nn phn cc

ca nhm OH trong phenol lnhn trong alcol,anion phenolat nnhhn so vi anion alcolat.

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Vi nhng nhm thht electron s lm tngtnh acid, v d nhNO2, COOH, CHO...

Vi nhng nhm th yelectron s lm gim tnhacid, v d nh CH3,C2H5, ...

Tnh acidcn ph thuc v tr cc nhm th do hiu ngkhng gian, hiu ng cm ng, lin hp...

V d nh vi cc ng phn ca cresol th ng phn meta c lcacidmnh nht do t b nh hng bi hiu ng siu lin hp, ng

phn ortho c lc acidyu nht bi nh hng thm ca hiu ngkhng gian, lm cn tr s lin hp vo vng thm

C6H5OH C6H5O- + H+*Phnngca nhm OH

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nh hng ca cc nhm th:

*Phnngca nhm OH

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p/ tophc

6C6H5OH+FeCl3 [Fe(OC6H5)6]3-+6H++3Cl-

Phc mu tm

viNa2CO3

C6H5OH+Na2CO3

C6H5ONa+NaHCO3

vi kimloikim

phh

C6H5OH + NaC6H5OH+ H2vi dd kim

C6H5OH + NaOHC6H5ONa+ H2O

Phnngca nhm OH

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2.Phn ng to thnh ether:

Mun iu ch ether ca phenol ta khng th dng phngphp un nng phenol vi H2SO4 c, m phi cho phenol dng mui phenolat tc dng vi dn xut halogen cahydrocarbon.

( ) ( )6 5 2 3 6 5 2 3

I

C H O Na Br C H CH C H O CH CH NaBr

Phn ng ny xy ra theo c ch SN2, cho nn dn xut halogenbc I d phn ng hn dn xut bc II v nht l hn bc III.

Thm ch, dn xutbc III cn cho sn phm theo c ch E1 lhng chnh:

6 5 3 3 6 5 3 2 2( ) ( )C H ONa CH C Br C H OH CH C CH NaBr

*Phnngca nhm OH

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IV.Tnh cht ha hc3.Phn ngto ester RCOOC6H5

- Phenol rt kh tham giaphnng ester ha trctipviRCOOH v coi nh khngphnng. iuch este caphenolphi dng anhydrid acid hay clorid acid cho tc dngvi phenol trong mi trng base (NaOH hoc pyridin)

C6H5OH+(RCO)2O C6H5OCOR+RCOOH

C6H5OH+RCOCl C6H5OCOR +HCl

- cbit dng clorid acid thm c nhiuthunli v ester tothnh t tan v kt tinh tt.

C6H5 OH + C6H5COCl C6H5OCOC6H5 +HClNaOH

Phenyl benzoat (96%)

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IV.Tnh cht ha hc

4.Phn ngth nhm OH- Phenol khng tc dngvi HX tr khi trong vng

benzen c nhm ht e. Vi PCl5 phenol cphnngnhnghiusutrtthp.

+ POCl3 + HCl

*Phnngca nhm OH

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IV.Tnh cht ha hc

-Nu trong phenol c nhiu nhm ht e th c thphnngvi PCl3 :

Acid picric

PCl3

1-clo-2,4,6-trinitrophenol

-Vi PCl3, phenol chto ra este ca acid photphorm

khng to ra C6H5Cl:

3C6H5OH+PCl3 P(OC6H5)3 + 3HCl

*Phnngca nhm OH

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-Mt s phenol khi un nng p sut vnhit cao trong s c mt ca mui amonichuyn thnh amin thm.

ArOH + NH3 ArNH2 + H2O

Phn ng ny ng dng vi naphtol v mt sdiphenol

IV.Tnh cht ha hc

*Phnngca nhm OH

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IV.Tnh cht ha hc

1.Phn ng brom ha

- Chcn nhit phng, brom trong nc c thth

mtln vo 3 v tr trong nhn benzen ca phenol.

+ Br2 +3HBr

BrBr

Br

H2O

25oC

95%

*Phnngthnguyn tH vo vng benzenSE

(Ar)

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IV.Tnh cht ha hc

- Nu brom ha trong dung mi km phn

cc (CCl4,CS2) thphnng c thdng

snphmth monobrom phenol:

Br

Br

++Br2-HBr

CS2,0oC

*Phnngthnguyn tH vo vng benzenSE(Ar)

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IV. Tnh cht ha hc

- Brom ha trong 1,2-dicloetan sutin tosnphm p-bromphenol

Br

+ HBr

93%

+ Br20

o

C

ClCH2CH2Cl


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IV. Tnh cht ha hc

2.Phn ng nitro ha.- Phenolb nitro ha ngay 0oCbng HNO3 long

(19%) to ra snphm o- v p-nitrophenol

NO2

NO2

+

HNO319%,0oC


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IV. Tnh cht ha hc

- Vihnhp HNO3c, H2SO4cthu c acid picric

+ 3HONO2+3H2O

H2SO4c


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IV. Tnh cht ha hc

3.Phn ng sunfo ha.- Snphm l ng phn ortho hay paraphthucnhit.

SO3H

20o

C

H2SO4

H2SO4

100oC

SO3H 100oC

Acid p-

hydroxybenzensunfonic


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IV. Tnh cht ha hc

4.Phn ng alkyl ha.

- Phnng alkyl ha phenol cthchinvi alcolhoc alken khi c mtcht xc tc

CH3 CH3

C(CH3)3

+(CH3)3COH +H2O

H3PO4

60oC


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IV. Tnh cht ha hc

CH3 CH3

C(CH3)3(CH3)3C

+CH3-C=CH2

CH3

xt

ionol


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IV. Tnh cht ha hc

*Phnngvianhydrid phtalic

Phenolphtalein

+

+un nng phenol vi anhydrid phtalic trong s c mt caH2SO4m c s to ra phenolphtalein.+Trong mi trng kim phenolphtalein chuyn thnh dng

quinon c mu. V vy n c lm cht ch th mu trong phntch kim nghim.

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IV. Tnh cht ha hc

5.Phn ng Reimer-Tiemann.

+CHCl3+3NaOHCHO

+NaCl+H2O

salicaldehyd

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Cch:

IV. Tnh cht ha hc

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IV. Tnh cht ha hc

6.Phn ngchuynv Claisen.

OCH2CH=CH2

CH2CH=CH2

BrCH2CH=CH2

NaOH

100-150oC

2-allylphenol

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IV. Tnh cht ha hc

7. Phnngvi aldehyd formic

n +2nHCHO

CH2

n

H+

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IV. Tnh cht ha hc

*Phnngoxy haKhc vi alcol thm v benzen, phenol db oxy ha v nhnthmdb ph vhn.

- Vi khng kh, cc phenolb oxy ha thnh nhiuhpcht mu,

v vy phenol lu ngy thng c mu hoc nu sm.- Vi H2O2hoc acid cromic, phenol to thnh para hydroquinon,sau l para benzoquinon v cui cng to thnh acid oxalic :OH

OH

OH O

O

COOH

COOH

p-hydroquinon p-benzoquinon Acid oxalic

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IV. Tnh cht ha hc

- Vi KMnO4hoc acid peracetic vng thmca phenolb ph vto thnh acid muconic

*Phnngoxy ha

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- Iod trong mi trng kim nng va cho snphm th, va cho phn ng oxy ha to ra tetraiodo

diphenylen quinon (hay Lautemann) khng tan.

IV. Tnh cht ha hc

*Phnngoxy ha

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IV. Tnh cht ha hc

-oxy habnghnhp sulfocromic to ra p-benzoquinon v cc snphm oxy ha tip theo.

*Phnngoxy ha

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Cc diphenol d tan trong kim to thnh cc mono-,diphenolat.Ring pyrocatechin tc dng vi mui ch to hp cht khng tan.

Phn ng ny dng phn bit pyrocatechin vi cc diphenolkhc.

Ortho v para diphenol d dng b oxy ha to thnh cc quinon

o- benzoquinon

IV. Tnh cht ha hc*Phnngoxy ha

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IV. Tnh cht ha hc

*Phnnghydro haHydro ha: Phenol b hydro ha c Ni lm xc tc tora cyclohexanol

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*Tc dng vi CO2tng hp acidKhi cho natriphenolat tc dng vi CO2 125oC dip sut th nhm COOH th vo v tr ortho i vinhmOH.

y l phn ng Kolbe- Schmitt.

+ CO2

Nhm phn ng xy ra nhit cao hn(250-300oC)v c bit khi dng mui kali phenolat th phn ngxy ra ch yu v tr para.

IV. Tnh cht ha hc

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T nha than :

Cch thc hin: ngi ta chng ct nha than 170-240oC ri thu c phn du trung bnh,

chuyn phenol cng ng ng c trong du thnhmui phenolat C6H5ONa ha tan bng NaOH ridng CO2hoc H2SO4 tch ly phenol v ngng ca n. Cui cng, chng ct phn on

thu phenol cng ng ng.

Tng hp t benzen:

T clorobenzen thng qua s :

T cumen:

T anilin v mui iazoni:

2 2 2

6 6 6 5 6 5 6 5, .( )o

Cl CO H ONaOHdac

t p caoFe t CC H C H Cl C H ONa C H OH

2 3 2( )

3 2

1. ( )

6 6 6 5 3 2 6 52. ,100( ) o

CH CH CH O kk

AlCl H O CC H C H CH CH C H OH

Cumen

C6H5NH2 + HNO2 + H2SO4 C6H5N2(+)HSO4(-) + 2H2O

C6H5N2(+)HSO4

(-) +H2O (nhit) C6H5OH + N2 + H2SO4

Benzendiazoni hidrosunfat

T cc benzenesunfonic acid

C6H5-SO3H + NaOH C6H5-SO3Na + H2O

C6H5-SO3Na + HCl C6H5OH + NaCl + SO2

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Phenol thng ( C6H5OH) hay cresol c dng ty u nh

ca v st trng dng c. Trong cng nghip, n l ngunnguyn liu tng hp phm nhum v cc cht do,Hydroquinon v cc dn xut ca n c s dng trong cngngh phim nh v n c th kh ion Ag+

Chuyn ha thun nghch gia hydroquinon v quinon ngmt vai tr quan trng trong mt s qu trnh oxy ha sinhhcNhng hp cht nh

polyphenol thc vt hay

vitamin E ng vai tr chtchng oxy ha v chng c khnng ph hy cc gc t doperoxyd RCOO*trong c th

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c bit, trong lnh vc Y hc, phenol c nhiu ng dng quantrng:

Phenol l ngun nguyn liu iu ch nhiu dc phm:

Aspirin c tc dng gimau, hst, chngvim; n cn c tcdng chng kt tp tiu cu, khi dng liu thp ko di c th phngnga au tim v hnh thnh cc nghn trong mch mu.

Metyl salixilat dng lm thuc gim au:

HO-C6H4-COO-CH3

Trong tinh du hng nhu, c mt dn xut ca phenol tn leugenol hay 4-anlyl-2-metoxiphenol c dng trong charng (kh trng, gim au..) v tng hp cht metyleugenol

phc v nng nghip (dn d rui vng hi cam vo by dit)

(Eugenol)

Tuy phenol c song mt nghin cu mi nht ca cc nh

khoa hc thuc i hc Cordoba (Ty BanNha) khm phnguyn l c bn v cng dng trn ca du liu, v pht hincht phenol trong du liu c th gy c ch i vi mt s genc hi trong c th v ang trin khai v nghin cu v d nny.
http://vi.wikipedia.org/wiki/%C4%90auhttp://vi.wikipedia.org/wiki/S%E1%BB%91thttp://vi.wikipedia.org/wiki/Vi%C3%AAmhttp://vi.wikipedia.org/wiki/%C4%90auhttp://vi.wikipedia.org/wiki/S%E1%BB%91thttp://vi.wikipedia.org/wiki/Vi%C3%AAmhttp://vi.wikipedia.org/wiki/Vi%C3%AAmhttp://vi.wikipedia.org/wiki/S%E1%BB%91thttp://vi.wikipedia.org/wiki/%C4%90au

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Phm nhumCh xanhVitamin E

Thuc n TNT

Thuc kch thch tng trng

2,4-D

Cht ty ra

Cht do

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Phenol: C6H5OH.Phenol cn c tn gi l acid phenic hay acid carbolic. L tinhth khng mu, ngoi khng kh b oxy ha chuyn thnh muhng,c mi c bit , n da. Vi nc, phenol to thnh hydratkt tinh C

6

H5

OH.H2

O, nng chy 15oC. Phenol tan trong ncvi t l 1: 15 ( 20oC). Phenol trn vi campho hoc menthol tothnh hn hp lng. Phenol lm ngng kt albumin nn c tcdng st khun, dung dch 1: 10 dng ty u.

Phenol c dng nhiu trong cng nghip cht do (nha

Bakelit), iu ch acid salicylic, acid picric, thuc nhum, cht ditc (acid phenoxy acetic, acid 2, 4-diclorophenoxy acetic).

VIII.Mtschtin hnh

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Cresol cng vi phenol c trong du carbolic thu c khi ctkhan than . Cresol tn ti vi 3 dng ng phn ortho, meta vpara.

Tch o-cresol d dng bng ct phn on, m-cresol v p-cresolkh tch ring v im si gn nhau nn phi sulfo ha trc khitch ring. Thng ngi ta khng tch ring 3 ng phn m dngdi dng hn hp tyu

VIII. Mtschtin hnh

VIII Mt ht i h h

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Thymol c trong tinh du thymus, l cht kt tinh, nng chy 50oC, dng tr sn. Hydro ha thymol s thu c hn hp nhiung phn lp th ca menthol. Cacvacvol l ng phn him thy dng lng,tos 237-238oC, dng ty u.

VIII. Mtschtin hnh

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Naphtol l nhng cht kt tinh, t tan trong nc.

-Naphtol c khng dng trong y hc.

-Naphtol dng lm cht kh trng.

Naphtol c dng mt lng ln lm phm nhum.

L cht kt tinh mu vng, v ng. Nu un cn thn n nngchy 122oC, nu un mnh n s n.

VIII. Mtschtin hnh

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L nhng hp cht c nhiu nhm OH lin kt trc tip vinhn thm.

Diphenol:

y ch kho st diphenol benzoic. Hai nhm OH trong phnt diphenol c th cc v tr ortho, para v meta.

C 3 diphenol n gin nht

VIII. Mtschtin hnh

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Cht no trong cc cht sau c cimdndruivng hi cam:

A.Metyleugenol.B.4-anlyl-2-metoxiphenol.

C.Benzoquinon.

D.Antrol.

Bi tp

A

h h

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Eugenol c cng thc lOH

OCH3CH2=CHCH2

l thnhphn chnh ca tinh duhng nhu ,c dng

tnghpchtdndrui vng metyleugenol theo s:Chtlng khng tan

Tinh duhng nhu(khng tan trong nc)

Dung dch trong nc metyleugenol(khng tan trong nc)

+NaOH

Giithch:

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Cho cc cht sau:(1) acid phenic,(2)m-cresol,(3)o-nitrophenol. Spxp theo chiu

tnh acid tngdn:A. (1),(2),(3).B. (2),(1),(3)

C. (3),(1),(2)

D. (3),(2),(1)

Bi tp

B

Bi t

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Bi tp

Cht no trong cc cht sau c dng trongcharng:

A.4-anlyl-2-metoxiphenol.B.4-metylaminophenol.

C.4-aminophenol.

D. phenol

Bi

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iuch este ca phenol ngi taphi dngdnxutca acid cho tc dngvi phenol trong

mi trng :A.Base: NaOH hoc pyridin.B.Acid: H2SO4c

C.Mi trng trung tnhD. C thxy ra c ba mi trng

Bi tp

A

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Chn cu ng:

A.Phnngca aryl halogenua din ra theo cch SN1 hoc SN2.

B.Phenolat ca Fe tophc mu hng.

C.Vi PCl3,phenol chto ra este ca acid

photphoro m khng to ra C6H5Cl

D.Vi PCl5 phenolphnngthiusutrtcao.

C

Bi tp

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Cho cc cht :phenol,ethanol,ethyl clorua. Ktlun no ng:A.C mtcht tc dngvi Na.

B.C 2 cht khng tc dngvi dd NaOH.

C.C 2 cht tc dngcvi NaOH.

D.C 3 chtu tan tt trong nc.

C

Bi tp

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58

Bi tp:

Su nguyn t carbon trong phenol

u trng thi lai ha:A. sp B. sp2

C. sp3 D. sp3d

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Bi tp:

Ch ra nhn nh ng:

A. Phenol tan tttrong nc iu kin thngdo to clin kt hydro vi nc

B. lu trong khng kh, phenol t chy ra v bchuyn mu

C. Cc phenol u c nhit si ln hn 200oC

D. Phenol khng tan trong ether

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Bi tp:

Sp xp tnh acidtng dn ca cc cht sau: Phenol (1);

acid picric (2); o-cresol (3); p-cresol (4):A. 1, 2, 3, 4

B. 4, 3, 1, 2

C. 3, 4, 1, 2

D. 1, 4, 3, 2

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Bi tp:

iu ch ether ca phenol, ta cho phenolattc dng vi:

A. Dn xut halogen ca hydrocarbon

B. Alcol

C. Anhydrid acid

D. Clorua acid

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62

Bi tp:

Phn ng C6H5ONa+ClCH3 C6H5OCH3+NaCl xy ra

theo c ch:A. SN1

B. E1

C. AE

D. SN2

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63

Bi tp:

Trong cc phn ng sau, phn ng no xy ra theo c chSE:

A. C6H5ONa + Br-CH3

B. C6H5ONa + Br-C(CH3)3

C. m-C6H4(OH)(CH3) + HNO3

D. H2O+CH2=CH2 (xt H+)

SN2

SN1

SE

AE

p n Cng

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64

Bi tp:

Nhn nh no sai:

A. C th iu ch phenol t nha than

B. Phenol c th c dng ty u vst trng

C. Phenol rt bn vng trong mitrng cha cht oxy ha

D. Cc polyphenol thc vt, vitamin E ng

vai tr cht chng oxy ha trong c th

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65

Bi tp:

Tn ca cht l:

OH

A. 1-Antrol

B. Antraxen-3-ol

C. 5-Antrol

D. Antraxen-9-ol

Hay cn gi l 9-Antrol

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66

Bi tp:

S ng phn cha nhm chc phenol c cng

thc C8H10O l: ( =4)A. 8

B. 9

C. 10

D. 11

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