Tit : phenol

A.Mc ch yu cu
-Nm c c im cu to tnh cht ho hc ca phenol,so snh
ancol thm v phenol ,so snh tnh cht ho hc ca ancol v phenol,
nm c nh hng qua li gia cc nguyn t trong phn t v cc phng php iu ch phenol.
B. Trng tm
-Nm c khi nim ,cu to tnh cht ho hc , phn bit ancol thm
v phenol , nm c nh hng qua li gia cc nguyn t trong phn t
v cch iu ch phenol,
C.Chun b
Ho cht : phenol , dung dch NaOH , CO2 , dung dch Br2 . . .
Dng c : ng nghim , ng dn kh . . .
D.Ln lp
I.Kim tra bi c.
*nh ngha ,CTTQ ca ancol no n chc ? Cho clo, oxi, natri,
natrioxit , natri hidroxit , canxi oxit ,canxi hidroxit ,canxi cacbonat ,ancol
etylic,axit clo hidric , axit axetic.Ancol etylic phn ng c vi cht
no.Vit PTP.
*Cc phng php iu ch ancol no n chc ?Cho v d ?
II.Bi mi

HS vit CTCT ca benzen.Thay th

H trong phn t benzen v toluen
bng nhm OH.
+GV chiu phim slide v cu to
ca phenol v ancol thm.HS nhn
xt rt ra N phenol, ancol thm?
+Nu quy lut gi tn cc cht
thuc loi phenol ?
+HS quan st mu phenol rn v
phenol lng: nhn xt trng thi
mu sc v th tnh tan ?
+Nhn xt c im cu toca
ancol no n chc v phenol?
+Tnh cht ho hc ging v khc
nhau ?Nguyn nhn ?
+Trong hn hp phenol-nc c bao
nhiu kiu lin kt hidro ?Lin kt
no bn nht ?

1.Cng thc cu to.

*Phenol : l nhng hp cht hu c m phn t c nhm -OH lin kt trc
tip vi nguyn t C ca vng ben zen
*Ancol thm : l nhng hp cht hu c m phn t c nhm -OH lin kt
vi nguyn t C mch nhnh ca hidrocacbon thm.
Gi tn : v tr nhnh ,tn nhnh - phenol
2 .Tnh cht vt l
-Phenol l cht kt tinh khng mu c mi c trng ,Tnc= 430C, t tan trong nc lnh ,tan nhiu trong nc nng , rt c.
3 . Tnh cht ho hc
* Cu to : - C vng benzen
- C 1 nhm - OH ( ging vi ancol )

O H

O H
O H

phenol

catechol

(benzenol)

1,2-ihidroxibenzen
O H

O H

*GV lm th nghim : cho phenol

rn cho vo nc?Lc nh thm t
t dung dch NaOH.Lc nh?
Hin tng v gii thch?
+Tnh axit ca phenol ?
+Sc kh CO2 n d vo dung
dch thu c .Hin tng v gii
thch?

*GV lm Th nghim tc dng ca

phenol vi dung dch nc brom.
+GV hng dn hc sinh nhn xt
kh nng, mc phn ng da

O H
rezoxinol

O H
hidroquinol

1,3-ihidroxibenzen

1,4-ihidroxibenzen

a.Tnh axit
C6H5OH+ NaOHC6H5ONa+H2O
C6H5OH+ OH-C6H5O-+H2O
Phenol nhng H+ vy phenol l 1 axit
*Tnh axit ca phenol : Rt yu
- Khng lm i mu qu tm
-B axit mnh hn y ra khi mui phenolat
C6H5ONa+CO2+H2OC6H5OH+NaHCO3 ( Phenol c tnh axit yu hn
H2CO3)
-Tnh axit ca phenol mnh hn ancol: phenol tc dng vi NaOH cn ancol
th khng phn ng.
+Do nh hng ca vng benzen n nhm - OH lm cho nguyn t H trong
nhm - OH ca phenol linh ng hn ca ancol.

b.TcOH
dng vi nc brom

OH
Br

Br

+3HBr

+3Br
2

Br

vo iu kin , tc phn ng
nhn xt ?
+Hc sinh nhc li quy lut th
nguyn t H trong vng benzen ?
+Phn tch nh hng qua li gia
cc nguyn t v nhm nguyn t
trong phn t phenol ?
+ng dng ca phn ng ?
*Qui lut th nguyn t H vng
benzen?

+Nhm -OH nh hng n vng benzen lm cho phn ng din ra d hn

v nh hng th vo v tr o, p.
c.Vi HNO3

O H

O H
O2N
*GV cho HS c SGK phn ng
dng ca phenol .
+GV cho HS phn tch cu to ca
phenol v cch iu ch chng t
hidrocacbon tng ng v vit y
cc PTP .

NO2
+3 H 2O

+ HNO3
NO2
d.Vi hidro

O H

O H
N i,t 0
+3 H2

4.ng dng v iu ch
a).ng dng : sn xut cht do,t ho hc,thuc tr c,phm nhum
b). iu ch
*Tch chit t nha than
*Tng hp t benzen
C6H6+Cl2C6H5Cl+HCl ( Fe, t0)
C6H5Cl+NaOHC6H5OH+NaCl ( t0 , P cao )
*T Cumen ( iso propylbenzen ).
C6H6+ CH3-CH = CH2 C6H5-CH(CH3)2 ( H2SO4 hoc AlCl3 )
C6H5-CH(CH3)2 + O2 C6H5-C(O-O-H)(CH3)2
C6H5-C(O-O-H)(CH3)2 C6H5OH + CH3-CO-CH3 (dung dch H2SO4 long )
*T phenylaxetat :
C6H6 + ( CH3COOH, O2) C6H5OCOCH3 +( H2O , xt ) C6H5OH
C6H5OCOCH3 +( H2O , xt ) C6H5OH
III. Cng c..
*Cho ancol etylic,phenol,ancol benzylic,p-metylphenol,anisol.Cht no tc
dng vi Na,KOH,HCl,nc brom.Vit phng trnh phn ng.
*Nu v chng minh nh hng qua li gia cc nguyn t trong phn t
phenol.
*Vit PTP chng t rng tnh axit H2CO3 > C6H5OH
IV.Bi tp v nh. : 2-6.
1.So snh tnh axit ca C6H5OH v H2CO3
Axit H2CO3 l axit 2 nc trong nc 1 mnh hn phenol, nc 2 yu hn
phenol

OH

C6H5ONa+CO2+H2O C6H5OH+NaHCO3
C6H5OH+Na2CO3 C6H5ONa+NaHCO3
*iu kin hp cht thm tc dng vi dung dch Br2 :
+Phi c t nht mt trong cc nhm th sau gn vo nhn phenyl:-OH,NH2,-OR, NHR . . .
+Nhng
cht
no
sau
y
tc
dng
vi
nc
brom:benzen,anilin,nitrobenzen,ancol
benzylic,p-crezol,m-crezol,ocrezol,toluen,metylphenylete,metylphenylamin, ancol phenyl etylic.
d.To thnh ete : Cc phenolat tc dng vi dn xut halogen to thnh ete .
C6H5ONa+Br-CH2-CH3C6H5O-CH2-CH3+NaBr
Th t phn ng gim dn :
Dn xut halogen bc I > Dn xut halogen bc II > Dn xut halogen bc
III
e).Phn ng to thnh este: Tc dng vi anhidrit axit hoc clorua axit
C6H5OH+ (CH3CO)2O C6H5O-CO-CH3+ CH3COOH
C6H5OH+ CH3COCl C6H5O-CO-CH3+ HCl
f).Phn ng cng hidro to thnh xiclohecxanol
C6H5OH+ 3H2C6H11OH ( Ni , t0 C ).