PHENOL

Phenol l hp cht c nhm hidroxyl -OH gn trc tip vi vng benzen. i din n gin nht ca loi hp cht ny l hidroxybenzen (phenol). Cng thc tng qut ca cc phenol thng gp. Monophenol Ar-OH hoc CnH2n-7OH Polyphenol Ar'(OH)m CnH2m-6-m(OH)m m 2

PHENOL

MONOPHENOL

NG PHN DANH PHP

1. ng phn 2. Danh php Danh php thay th

- Phenol n gin nht l C6H5OH (phenol) - Gi tn ca phenol khc nh l dn xut ca phenol n gin nht

4-metylphenol

NG PHN DANH PHP

Tn ring c lu dng

thimol

PHNG PHP IU CH

Thy phn cc aren halogenua

Nung nng chy axit aren sulfonic vi NaOH

Oxi ho hp cht aryl magie halogenua ArMgX

PHNG PHP IU CH

Oxi ho cumen

PHNG PHP IU CH

Trong PTN c th iu ch phenol t mui diazoni ca hidrocacbon thm.

Ngoi ra, phenol cn thu c t sn phm chng ct nha than

TNH CHT VT L

S c mt nhm hidroxyl gn trc tip vo vng benzen quyt nh tnh cht vt l ca phenol. Do tng tc vi vng benzen, lin kt O-H b phn cc mnh hn O-H ca ancol. Lin kt hidro trong phenol bn hn lin kt hidro ca ancol. Phn ln cc phenol u dng rn, tan c trong nc v t bay hi.

TNH CHT HO HC

Nhm OH gn trc tip vo h thng lin hp ca vng benzen. Phenol c cu to nh mt enol CH=C-OH bn vng. Tnh cht ca phenol do nhm OH quyt nh. Phenol c tnh axit. Nhm chc -OH phenol l nhm th loi I, phn ng th xy ra trong vng benzen to hn hp ng phn ortho v para.

TNH CHT HO HC

Tnh axit Phenol c tnh axit mnh hn ancol. Cp electron trn oxy ca nhm -OH lin hp vi vng benzen. Hidro ca nhm O-H tr nn linh ng.

TNH CHT HO HC

Phn ng th hin tnh cht axit

TNH CHT HO HC

Phenol l mt axit yu, pKa ca mt s cht nh sau: Axit pKa Baz

HCl CO2+H2O C6H5OH HCO3H2O RCH2OH R2CHOH R3COH RCCH NH3 R2C=CH2 RH ClHCO3C6H5OCO32HORCH2OR2CHOR3CORCCNH2R2C=CHR-6 6,4 10 10,33 15,74 16 17 18 25 33 44 50

TNH CHT HO HC

Phn ng este ho ca phenol

H0 = +1,5 Kcal/mol

H0 = -4,6 Kcal/mol

TNH CHT HO HC

Phenol khng phn ng trc tip vi axit carboxylic to este m ch tc dng vi anhidrit axit hoc halogenua axit

TNH CHT HO HC

Phenol khng phn ng trc tip vi axit carboxylic to este m ch tc dng vi anhidrit axit hoc halogenua axit

TNH CHT HO HC

Este ca phenol tham gia phn ng chuyn v Fries to ceton thm khi c xc tc axit Lewis (AlCl3)

TNH CHT HO HC

Phn ng to ete ca phenol.

Cc phenolat tc dng vi alkyl halogenua to ete (Phn ng Williamson).

ArONa + RX ArOR + NaX

Cng c th cho phenolat phn ng vi dimetyl sunfat trong mi trng kim

ArONa + (CH3)2SO4 ArOCH3 + Na2SO4

TNH CHT HO HC
Khi un nng, ete cha no dng allylphenyl ete tham gia chuyn v Claisen

TNH CHT HO HC

Phn ng thay th nhm OH.

Nhm -OH phenol c th b thay th bi -Cl hoc -NH2 khi tc dng vi PCl5 hoc NH3 vi xc tc AlCl3.

TNH CHT HO HC

Phn ng vi andehit
Phenol tc dng vi andehit focmic trong mi trng baz to hn hp ancol ortho v para-hidroxybezylic.

TNH CHT HO HC

Phn ng vi andehit
Phn ng xy ra kh iu khin v tc . Cc ancol to thnh tng tc vi nhau tng t phn ng trng ngng v to thnh polime gi l bakelit. n HOC6H4CH2OH

TNH CHT HO HC

Phn ng tng hp Kolbe. Tng hp axit salicylic

Phenolat natri tc dng vi CO2 c p sut v nhit to salixilat natri.

TNH CHT HO HC

Phn ng fomyl ho: Reimer- Tieman

Phenol tc dng vi cloroform trong mi trng kim mnh to thnh hidroxy-benzandehit. Sn phm phn ng c th l hn hp ng phn ortho v para.

TNH CHT HO HC

Phn ng fomyl ho: Reimer- Tieman

C ch nh sau CHCl3 + NaOH :CCl2 + H2O + NaCl

TNH CHT HO HC

Phn ng fomyl ho: Gattermann

TNH CHT HO HC

Phn ng fomyl ho: Gattermann - Adam

Phng php ny s dng Zn(CN)2 nn c hn Zn(CN)2 + HCl 2HCN + ZnCl2

ng thi ZnCl2 sinh ra lm xc tc cho phn ng thay th cho AlCl3.

TNH CHT HO HC

Phn ng ankyl ho
Ankyl ho phenol bng ancol hoc anken vi xc tc axit (khng dng AlCl3). C th dng axit p-toluensunfonic, nhm phenolat hoc nha cationit
OH H3C C CH3 CH2
H2SO4 100-120oC

HO

C(CH3)3

TNH CHT HO HC

Phn ng ankyl ho
Ankyl ho phenol bng ancol hoc anken vi xc tc axit (khng dng AlCl3). C th dng axit p-toluensunfonic, nhm phenolat hoc nha cationit OH OH

+ CH3OH

Al2O3 200-290oC

CH3

TNH CHT HO HC

Mt s phn ng th electronphin khc

Phenol tham gia cc phn ng th electronphin khc nh nitro ha to cc hp cht nitrophenol; Phn ng halogen ho to hp cht halogenphenol. Phn ng sulfon ho to axit hidroxybenzensulfonic.

TNH CHT HO HC

Mt s phn ng th electronphin khc

TNH CHT HO HC

Phn ng to mu vi dung dch FeCl3.

Vi dung dch FeCl3 phenol to hp cht C6H5OFeCl2 c dung dch mu tm-; Cresol to dung dch mu xanh v cc phenol khc to dung dch mu vng.

TNH CHT HO HC

Phn ng oxy ho phenol.

Phenol d b ho nu bi oxy khng kh. Nhiu phn ng oxy ho ca phenol xy ra rt phc tp. Tnh cht ca sn phm ph thuc vo bn cht ca nhm th.
OH [ O] - H. O. O O O

. .

TNH CHT HO HC

Phn ng oxy ho phenol.

Oxyt cromic CrO3 oxy ho phenol to p-benzoquinon. Phn ng xy ra qua giai on to axit phenylcromat.
OH + CrO3 O_CrO3H

;
H O

O_CrO3H - H2CrO3 H O H H H

OH H2CrO4 OH OH p- Hydroquinon

O p- Benzoquinon

PHENOL

POLIPHENOL