Benzen C

6
H
6
1. Cu to - ng phn - tn gi
a) Cu to
Phn t benzen c cu to vng 6 cnh u. Mi nguyn t C trong phn t benzen
tham gia 3 lin kt vi 2C bn cnh v H nh 3 obitan lai ho sp
2
nn tt c cc nguyn
t C v H u nm trn cng mt phng. Cn mi lin kt th 4 (lin kt ) c to nn
nh obitan 2p c trc vung gc vi mt phng phn t. Khong cch gia cc nguyn t
C trong phn t l bng nhau nn my electron p ca nguyn t C xen ph u vi 2 my
electron 2p ca 2 nguyn t C bn cnh, do trong phn t benzen khng hnh thnh 3
lin kt ring bit m l mt h lin kt thng nht gi l h lin hp thm, quyt
nh nhng tnh cht thm c trng ca nhn benzen; va th hin tnh cht no, va th
hin tnh cht cha no.
V th CTCT ca benzen thng c biu din bng my cch sau:

Gc hirocacbon thm
Khi tch bt 1H khi phn t benzen ta c gc phenyl C
6
H
5
-
Khi tch bt 1H khi nguyn t C trn nhn benzen ca 1 phn t hirocacbon thm ta
c gc aryl.
Nu tch 2H th c gc phenylen v arylen
b) ng phn
V cc lin kt C - C trong nhn benzen ng nht nn benzen ch c 3 ng phn v
tr.
Nu hai nhm th hai C ln cn ta c ng phn ortho (vit tt l o-) hoc nh s
1, 2.
Nu hai nhm th cch nhau mt nguyn t C (mt nh lc gic gi l ng phn
meta (vit tt l m-) hoc 1, 3.
Nu hai nhm th hai nguyn t C i nh gi l ng phn para (vit tt l p-)
hoc 1, 4.
V d: Cc ng phn ca iclobenzen C
6
H
4
Cl
2
.

2. Tnh cht vt l
Benzen l cht lng khng mu, rt linh ng, c mi c trng, nhit si = 80
o
C.
Benzen nh hn nc, khng tan trong nc, nhng tan nhiu trong cc dung mi
hu c nh ru, ete, axeton.
Benzen l dung mi tt ho tan nhiu cht nh Cl
2,
Br
2,
I
2,
S, P,cht bo, cao su.
Nhng cht n gin nht trong dy ng ng ca benzen l cht lng, nhng ng
ng cao hn l cht rn.
Benzen c dng lm nguyn liu u iu ch thuc nhum, thuc cha bnh,
si tng hp, cht do, phenol, nitrobenzen, anilin.
Benzen l mt trong nhng dung mi hu c tt nht.
3. Tnh cht ho hc ca benzen.
Benzen va tham gia phn ng th va tham gia phn ng cng, trong phn ng
th c trng hn, chng t nhn benzen rt bn. c im ca benzen gi chung l
tnh thm.
a) Phn ng th: D dng hn hirocacbon no mch h.
Vi halogen nguyn cht (Cl
2
, Br
2
) phn ng xy ra nhit thng c v bo st
xc tc:
(brombenzen)
Ch : Bnh thng benzen khng lm mt mu nc brom.
Phn ng nitro ho: Vi HNO
3
bc khi, c mt H
2
SO
4
c, un nng nh.
Phn ng vi H
2
SO
4
c
Phn ng vi dn xut halogen
b) Phn ng cng: Kh xy ra hn hirocacbon cha no, mch h.
Cng hp hiro
Cng hp clo v brom
4. Tnh cht ho hc ca cc ng ng benzen
a) Phn ng th
Th trn nhn benzen. Phn ng th trn nhn benzen ca cc ng ng ph thuc
vo nh hng ca nhm th c sn i vi nhn benzen. Ngi ta chia thnh 2 loi.
+ Nhm th l nhm y electron:
Khi trn nhn benzen c nhm th y electron nh - NH
2
, - NR, - OH,
- OCH
3
, gc ankyl - R, (+C, +H) lm mt electron cc v tr ortho v para
tng, do phn ng th xy ra d hn (nh hng th vo v tr o-, p-).
V d phn t toluen C
6
H
5
- CH
3

+ Nhm th l nhm ht electron
Khi trn nhn benzen c nhm th ht electron nh - NO
2
, - SO
3
H, - COOH,
- CHO (
-
C) lm gim mt electron v tr meta c tri hn (nh hng th vo
v tr m-).
V d phn t C
6
H
5

-
NO
2

Sau y l phn ng th ca Br
2
ng vi 2 trng hp trn.

Th trn gc ankyl: Vi halogen xy ra khi chiu sng khng c xc tc.
b) Phn ng oxi ho:
Cc cht oxi ho mnh (nh KMnO
4
) oxi ho nguyn t C ca mch nhnh nh trc
tip vi nhn benzen:
5. iu ch
a) iu ch benzen
Chng ct nha than .
T axetilen:
T xiclohexan.
T n - hexan.
b) iu ch cc hirocacbon thm khc
Gii thiu mt s hirocacbon thm
a) Tuloen C
6
H
5
- CH
3
: l cht lng (nhit si = 111
o
C), c mi ging benzen, khng
tan trong nc, tan trong mt s dung mi hu c.
b) Etylbenzen C
6
H
5
- CH
2
- CH
3
l cht lng khng mu, c mi ging benzen (nhit
si = 136
o
C), t tan trong nc.
Ngoi cc tnh cht ca hirocacbon thm cn c phn ng tch H
2
:
c) Stiren C
6
H
5
- CH = CH
2
l cht lng (nhit si = 145
o
C). t tan trong nc, tan
nhiu trong ru, ete, xeton.
D tham gia phn ng cng ni i ca mch nhnh.
Phn ng trng hp xy ra rt d dng khi c mt cht xc tc:
Polistiren l cht rn trong sut, d gia cng nhit, dng lm vt liu in, dng c gia
nh
Stiren ng trng hp vi butaien to thnh cao su butaien stiren.
d) Xilen C
6
H
4
(CH)
3
: c 3 dng.

e) Hirocacbon thm c nhiu vng benzen.
iphenyl C
6
H
5
- C
6
H
5
: cht rn, tan trong ru, ete.
Naphtalen C
10
H
8
:


Cht rn
Antraxen C
14
H
10

BI TP V AREN
1.
4 3 3 4
12 4 3 Al C HCl AlCl CH + +
2.
1500
4 2 2 2
m lanh nhanh
2 3
o
C
l
CH C H H +
3.
600
2 2 6 6
3
o
C
C
C H C H
4.
6 12 6 6 2
300
3
o
Pd
C
C H C H H +
5.
6 6 2 6 12
3
o
Ni
t
C H H C H +
6.
t
6 6 2 6 5
bo Fe
C H Br C H Br HBr + +
7.
3
6 6 3 6 5 3
AlCl
C H Cl CH C H CH HCl + +
8.
[ ]
4
6 5 3 6 5 2
3
o
ddKMnO
t
C H CH O C H COOH H O + +
9.
6 5 6 5 2
C H COOH NaOH C H COONa H O + +
10.
6 5 6 5
C H COONa HCl C H COOH NaCl + +
11.
o
i ti
6 5 ( nh th) ( ) 6 6 2 3
t
v
ti r
C H COONa NaOH C H Na CO + +
12.
s'
6 6 2 6 6 6
3 C H Cl C H Cl +
13.
6 12 6 6 2
300
3
o
Pd
C
C H C H H +
14.
900
3 2
o
C
CaCO CaO CO +
15.
2000
2
3
o
C
CaO C CaC CO + +
16.
( )
2 2 2 2
2
2 CaC H O Ca OH C H + +
17.
600
2 2 6 6
3
o
C
C
C H C H
18.
3
6 6 3 6 5 3
AlCl
C H Cl CH C H CH HCl + +
19.
20.
2 5 2 4 10 2 2
2 2 2
dpdd
C H COONa H O C H NaOH CO H + + + +
21.
4 10 3 6 4
600
o
Cracking
C
C H C H CH +
22.
1500
4 2 2 2
m lanh nhanh
2 3
o
C
l
CH C H H +
23.
600
2 2 6 6
3
o
C
C
C H C H
24.
25.
7 16 6 5 3 2
4
o
Dehidro
t
C H C H CH H +
26.
s'
6 5 3 2 6 5 2
C H CH Br C H CH Br HBr + +
27.
6 5 2 2 6 5 2
OH
C H CH Br H O C H CH OH HBr

+ +
28.
2 4
( )
3 2 6 5 3 2 6 5 2
H SO d
CH COOH HO CH C H CH COOCH C H H O + +

29.
6 5 2 3 2 6 5 2 2
C H CH CH Cl C H CH CH Cl HCl + +
30. 6 5 2 3 2 6 5 3
|
C H CH CH Cl C H CH CH HCl
Cl
+ +
31.
6 5 2 2 2 6 5 2 2
OH
C H CH CH Cl H O C H CH CH OH HCl + +
32.
6 5 2 2 6 5 2 2
o
t
C H CH CH OH CuO C H CH CHO Cu H O + + +
33.
( )
6 5 2 3 6 5 2 4 3 2
2
2 3 2
o
t
C H CH CHO Ag NH OH C H CH COONH NH Ag H O 1 + + + +
]
34.
( )
6 5 2 4 2 4 6 5 2 4 4
2
2 2 C H CH COONH H SO C H CH COOH NH SO + +
35. 6 5 3 2 6 5 3
| |
OH
C H CH CH H O C H CH CH HCl
Cl OH

+ +
36.
2 4
( )
6 5 3 6 5 2 2
|
o
H SO d
t
C H CH CH C H CH CH H O
OH
+
37.
6 5 2 2
|
6 5
n
nC H CH CH CH CH
C H
_




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