Chng 7: hirocacbon thm

ngun hirocacbon thin nhin

Hirocacbon thm(aren) l nhng
hirocacbon trong phn t c cha mt
hay nhiu vng benzen.
Khi phn t ch c mt vng benzen th

c gi l aren n vng
Khi phn t c nhiu vng benzen th

c gi l aren a vng

S GIO DC V O TO TP. CN TH
TRNG TRUNG HC PH THNG NGUYN VIT HNG

GVHD: NG TH BCH THU

GSTG: HUNH VN T

BI 46:

BENZEN V ANKYLBENZEN

I CAU TRUC , ONG ANG , ONG PHAN VA

DANH PHAP :
1 - Cau truc cua phan t benzen :
a/ S hnh thanh lien ket trong phan t benzen

Hay mo ta s
hnh thanh lien
ket trong phan
t bezen ?
Trang thai lai hoa cua Cacbon? S xen phu cac
AO ,hnh thanh lien ket ?

2s

2p

- Nguyen t C trang thai

lai hoa sp2 .
Moi C s dung 3 AO lai hoa
e tao lien ket vi 2
nguyen t C ben canh no va
mot nguyen t H
Sau AO p con lai cua 6
nguyen t C xen phu ben vi
nhau tao thanh AO chung cho
ca vong ,tao he lien hp
thm ben vng .

BI 46:

BENZEN V ANKYLBENZEN

I CAU TRUC , ONG ANG , ONG PHAN VA

DANH PHAP :
1 - Cau truc cua phan t benzen :
a/ S hnh thanh lien ket trong phan t benzen

- Nguyen t C trang thai lai hoa sp 2 .

- Moi C s dung 3 AO lai hoa e tao lien ket vi 2
nguyen t C ben canh no va mot nguyen t H
- Sau AO p con lai cua 6 nguyen t C xen phu ben vi
nhau tao thanh AO chung cho ca vong ,tao he lien hp

b/ Mo hnh phan t :
Mo hnh rong

Mo hnh
ac

- Phan t benzen co hnh luc giac

eu
- Cac nguyen t nam trong mot mat phang cac
goc hoa tr eu bang 1200 .

c/ Bieu dien cau tao cua

benzen :

2- ong ang ,ong phan va

danh
phap :
a/ ong
: cac nguyen t hiro trong phan t benzen
-ang
Khi thay
bang cac nhom ankyl , ta c nhom ankylbenzen , hp
thanh mot day ong ang cua benzen : CnH2n-6 (n 6)
C6H5CH3

C6H5CH2CH3

C6H5CH2CH2CH3

2- ong ang ,ong phan va

danh
phap :
a/ ong ang

CH3
(o)6

b/ ong phan va danh

:
-phap
Ankylbenzen
co ong phan
mach cacbon va ong phan
v tr nhom the tren vong
benzen .
CH2CH3

CH3

1
2(o)
3(m)

(m)5
4(p)
CH3

Metyl benzen
(toluen)CH
3

CH3

etylbenzen

1,2oimetylbenzen
imetylbenzen
(0 xilen )

CH3
Viet
cac CTCT CH3
1,4 imetyl cua1,3
imetylbenzen
benzen
p- imetylbenzen
m
?
C6H5CH2CH
3

(p- xilen)

imetylbenzen
(m xilen )

-Goi ten : So ch v tr + ten nhanh + benzen .

- V tr cac nguyen t C cua vong goi bang ch so

hoac cac ch cai ;[1-2;1-6 goi la ortho (o)],[1-3 ,1-5 goi
la meta (m)]; [1-4 goi la para (p).

6
5

R1

R1
2

2
3
4

1+3 =4

R2

6
5

3
4

1+5=6

R2

CTCT
CTCT

CTPT

Tn thng thng

C6H6
C7H8

CH3
CH2CH3

CH3

Benzen

benzen

toluen

metylbenzen

etylbenzen
Cac chat trong
day on
benzen co so cacbon la b
1,2-imetylbenzen
nhieu th co ong phan
0-xilen
(o-imetylbenzen)

CH3

CC88H
H1010

CH3

m-xilen

H3C
H3C

Tn thay th

CH3 p-xilen

1,3-imetylbenzen
(m-imetylbenzen)
1,4-imetylbenzen
(p-imetylbenzen)

Chn p n ng .
CH3
Cng thc

C2H5

C tn gi l :

3
CH

C2H5
a. 4,6-ietyl-1,3-metylbenzen
b. 2,4-ietyl-1,5-imetylbenzen
c. 1,5-metyl-2,4-etylbenzen
d. 2,4-ietyl-1,5-metylbenzen

II TNH CHAT VAT

LY
:
1
Nhiet
o nong chay , t0s va khoi
lng rieng :
Aren

Cong
thc
phan t

tnc ,oC

t s , oC

D , g/cm3
(20oC)

Benzen

C6H6

5,5

80

0,879

Toluen

C7H8

-95,0

111

0,867

Etylbenzen

C8H10

-95,0

136

0,867

o-Xilen

C8H10

-25,2

144

0,880

m-Xilen

C8H10

-47,9

139

0,864

p-Xilen

C8H10

13,2

138

0,861

n-Propylbenzen

C9H12

-99,5

159

0,862

Isopropylbenzen
(Cumen)

C9H12

-96,0

152

0,862

II TNH CHAT VAT

LY
:
1 Nhiet
o nong chay , t0s va khoi
lng rieng :

- Nhiet o nong chay nhn chung giam dan , co

s bat thng p- xilen :o xilen : m xilen .
- Nhiet o soi tang dan .
- Khoi lng rieng cac aren nho hn 1g/cm3 cac
aren nhe hn nc .
2 Mau sac,tnh tan va mui
:- La nhng chat khong mau , hau nh khong tan
trong nc , tan
nhieu
trong
dung
Thc
hin th
nghim
: moi hu c .
ong thi
dung
tantng
nhieu chat khac .
1 a. la
Benzen
vomoi
nchoa
Hin
- eu la chat
covo
mui
hai cho sc
b. Benzen
xng, nhng
Hinco
tng.
khoe .

2 - a- Iot vo nc Hin tng

b- Cho iot vo benzen lc nh ?
nhn xt ,kt lun ?

Benzen

BI 46:

BENZEN v ANKYLBENZEN

I CAU TRUC , ONG ANG , ONG PHAN VA

DANH
PHAP
: cua phan t
1 - Cau
truc
benzen :
2- ong ang ,ong phan va
danh phap:

II TNH CHAT VAT

LY
:
1 Nhiet
o nong chay , t0s va khoi
lng rieng :
2 - Mau sac,tnh tan va mui :

BI TP CNG C
1. Kt lun no sau y l ng ?
A Benzen l mt hirocacbon khng no mch vng
B Benzen v xiclohexan,6 cacbon to thnh
mt lc gic u.
C Benzen, 3 lin kt i ngn hn 3 lin kt n
D Benzen, 3 lin kt n v 3 lin kt i c
di bng nhau.

2. S ng phn hirocacbon
thm c cng thc C8H10 l:
A

3 Vit cng thc cu to ca cc hp cht sau:

A Etylbezen.
B 1,3,5 trimetylbenzen
C

p Clotoluen
CH3

CH3

CH2CH3

H3C

CH3

Cl

IV- IU CH V NG DNG
1. iu ch
* Benzen, toluen, xilen: tch ra bng cch chng ct
nha than , du m hoc t ankan, xicloankan.
xt, to

C6H6 + 4H2

CH3[CH2]4CH3
xt, to
CH3[CH2]5CH3

C6H5CH3 + 4H2

* eltylbenzen:
C6H6

+ CH2 = CH2

xt, to

C6H5CH2CH3

3CH

CH

3H2

600 c
than hot tnh

CH3
+

CH3Cl

AlCl3
t0

HCl

KIM TRA BI C

-Vit cng thc cu to v gi tn cc

ng phn ankylbenzen C8H10.
- Nhn xt v nhit si, khi lng
ring ca cc cht trong dy ng ng
benzen

CH2CH3

CH3
CH3

etylbenzen

CH3

CH3

CH3

1,3
imetylbenzen

m
imetylbenzen
(m xilen )

1,2imetylbenzen
oimetylbenzen
(0 xilen )

CH3

1,4 imetyl
benzen
p- imetylbenzen
(p- xilen)

Nhiet o nong chay , t0s va khoi

lng rieng :
Aren

Cong
thc
phan t

tnc ,oC

t s , oC

D , g/cm3
(20oC)

Benzen

C6H6

5,5

80

0,879

Toluen

C7H8

-95,0

111

0,867

Etylbenzen

C8H10

-95,0

136

0,867

o-Xilen

C8H10

-25,2

144

0,880

m-Xilen

C8H10

-47,9

139

0,864

p-Xilen

C8H10

13,2

138

0,861

n-Propylbenzen

C9H12

-99,5

159

0,862

Isopropylbenzen
(Cumen)

C9H12

-96,0

152

0,862

S GIO DC V O TO TP. CN TH
TRNG TRUNG HC PH THNG NGUYN VIT HNG

GVHD: NG TH BCH THU

GSTG: HUNH VN T

IV- TNH CHT HA HC

CH3

TRUNG TM PHN NG

IV/ TNH CHT HO HC:

Cc ng ng ca benzen c tnh cht ca
vng benzen v ca cc mch nhnh
1/ Phn ng th.

a)Th nguyn t H ca vng benzen

- Phn ng vi halogen.

th nghim benzen phn ng vi brom

C6H6
Br2

Bt Fe

H2 O

Qu tm
ha

M hnh phn ng .
H
C
H

+
H

Br Br

Xt:Bt Fe,to

C
H

+ Br2

Bt Fe,to

Br

+ HBr

Hy hon thnh phng trnh sau?

CH3
41%
Br
O-bromtoluen

CH3
+Br2

Fe, t0

CH3

+HBr
p-bromtoluen

59%

Br

CH3

+ Br2

AS

CH2Br
Benzylbromua

CH2 H Br-Br

+HBr

Khi cho toluen tc dng vi clo iu kin

c chiu sng th sn phm to thnh l:
A

o-clotoluen

m-clotoluen

p-clotoluen

Benzyl clorua

b. Phn ng nitro ho
+ HNO3()

H + HO-NO2

H2SO4,

NO2
+ H2O
Nitrobenzen

Khi d HNO3.

NO2

NO2
+

HNO3

NO2
1,3 initro benzen.

H2O

M t th nghim iu ch
nitro benzen
H2SO4,HNO3
my khuy.
sinh hn

C6H6
iu chnitro benzen

Cho nitrobenzen tc dng vi hn hp HNO3 v

H2SO4 theo t l mol 1:1 thu c sn phm l:

A Orthoinitrobenzen
B Metainitrobenzen
C 1,3,5-trinitrobenzen
D parainitrobenzen

Tng t nh phn ng vi Br2 cc

ankylbenzen phn ng vi axit nitric s cho
sn phn th vo v tr ortho v para.

CH3
CH3
+HNO3(),H2SO4 c

- H2O

2-nitrotoluen
NO2 (o-nitrotoluen)

CH3

4-nitrotoluen
(p-nitrotoluen)
NO2

- Quy tc th vng benzen

Khi vng benzen c gn sn nhm ankyl (hay cc
nhm OH, -NH2, -OCH3, ) phn ng th vo vng
s d dng hn v u tin xy ra cc v tr ortho v
para.
Ngc li, nu vng benzen c sn nhm NO2 (hoc
COOH, -CHO, -SO3H, ) phn ng th vo vng s
kh hn v u tin xy ra v tr meta.

Khi nhn benzen c hai nhm

th.
- khi nhm th no y in t mnh
hn s nh hng phn ng.
1. v d:
OH

OH
Br

Br2

OH

NO2

NO2
OH
Br

Br2

CH3

CH3

So snh kh nng nh hng o,p-.

-OH > -NH2 >-OR > -H > -Hal > -NO2 >-CN.
i vi halogenua l nhm ht in t nh
ng vn nh hng o- v p-.

Ti sao li c s nh hng vo
nhn benzen nh trn?
-khi nhn c nhm
y in t:

NH2

-S lin hp lm tng mt
electron trong nhn benzen
c bit l v tr o- v pv tr o-, p- c hot ho
phn ng xy ra d dng hn
so vi benzen

 Khi nhn benzen c nhm ht in t:

O
N
S lin hp lm gim mt
electron trong nhn benzen
nh hng -m

Ankylbenzen tham gia phn ng th vi brom s

u tin th vo:
A

otho;meta

Para;meta

Para

otho;para

d) C ch phn ng th vng benzen

Cc tiu phn mang in tch dng to
thnh do tc dng ca chng vi xc tc
mi l tc nhn tn cng trc tip vo
vng benzen.

C ch phn ng nitro
ho.
H2SO4
HSO4
HO-NO2

H
2
SO4
+

H2O-NO2

+
+

HSO4
H

H2O-NO2
NO2 +H2O
NO2

NO2

NO2
H

chm

NO2
+

nhanh

2/ Phn ng cng.
a) Cng hiro .
+ 3 H
2

Ni,t

Xiclohexan

b) Cng clo
+ 3Cl2

nh sng

Cl
Cl

Cl

Cl

Cl
Cl

hexacloran

benzen

toluen

dd
KMnO4

dd
KMnO4

3.Phn ng oxi ha .
a. Phn ng xi ha khng han ton.
iu kin thng benzen v cc ankylbenzen
khng tham gia phn ng vi KMnO 4 .
Khi c nhit th benzen cng khng phn
ng vi KMnO4 nhng cc ankyl benzen th
lm mt mu KMnO4
to
+ 2MnO2+ KOH+ H2O
+2KMnO4
CH3

Kali benzoat
COOK

b. Phn ng oxi ha hon ton

3n-3

CnH2n-6

O2

to

nCO2 +(n-3)H2O

Ho cht v du hiu dng phn bit

benzen v toluen:
A Dung dch KMnO -Mt mu tm
4
B Dung dch KMnO4, un nng -Mt mu tm
C Kh oxi C phn ng chy
D Dung dch Br2 - Mt mu dung dch Br2

V. ng dng
- Benzen: tng hp cht do, cao su, t
si, iu ch ra mt s dn xut khc
- Toluen sn xut thuc n TNT.
- Benzen,toluen, xilen lm dung mi.

V. ng dng ca Benzen:

Cht do

Phm nhum

Dc phm

BENZEN
Thuc n

Dung mi

Gii kht

Thuc tr su

Kt lun:
Benzen tng i d tham gia phn ng th,
kh tham gia phn ng cng v bn vng vi
cc cht oxiho. cng l tnh cht ho hc
c trng chung cho cc hirocacbon thm
nn c gi l tnh thm.

BI TP CNG C
1. Khi cho toluen tc dng vi kh clo ( xc tc
Fe, un nng ) vi t l mol 1: 1 ta thu c:
A

Benzyl clorua

m-clo toluen

6.6.6

D O-clo toluen v p-clo toluen

2. Hp cht thm A c cng thc phn t l C8H10. Cho A

tc dng vi dung dch KMnO4 to ra mt axit c cu
to i xng. A c tn gi nh th no?

etylbenzen

B o-metyltoluen
C

p-metyltoluen

D m-metyltoluen

3.NU QUY LUT TH VNG BENZEN?

NHM ANKYL (hay
* Khi vng benzen c sn
cc nhm OH, -NH2, -OCH3 ), p th vo
D DNG HN
vng
v u tin v tr
ORTHO
PARA
..
V
.
NHM NO2
* khi vng benzen c sn
(hoc cc nhm COOH, -SO3H ), p th
KH HN
vo vng ..v
u tin v tr
META
..

4. DNG CTCT VIT PTP V GI TN SN PHM

A Benzen tc dng brom lng c xc tc bt

st.
B Toluen tc dng axit nitric c xc tc axit
sunfuric c.
C Etylbenzen tc dng hidro c xc tc Ni, un
nng.

Bi tp.
Bi 1 :T benzen ,toluen v cc cht v
c iu ch : TNT; 2,4,6
tribromtoluen, axit m-brombenzoic,
m-nitrotoluen.
Bi 2: So snh phn ng th halogen
xy ra benzen vi metan.
Bi 3: Nhn bit cc hn hp 2 cht sau:
benzen v toluen; benzen v stiren;
benzen v xiclohexan.

DN D
V nh lm bi tp :
6,7,8,9,10 trong sch gio
khoa.