CU TO CH2 = CH2

Su obital p cn li ca 6 nguyn t C xen ph bn vi nhau to thnh h lin hp pi, tng i bn vng hn so vi lin kt pi cc anken hay hircacbon khng no khc

Aromaticity
Definition

Benzene is a cyclic compound which has a planar structure with a delocalized cloud of p-electrons above and below the plane of the ring:

I- CU TRC- NG NG - NG PHN - DANH PHP

Benzen tng i d tham gia phn ng th, kh tham gia phn ng cng v bn vng vi cc cht oxi ho. cng l tnh cht ha hc c trng chung ca cc hircacbon thm nn c gi l tnh thm

Vo thi k ny hu ht cc nh ha hc ngh rng khng th bit cu trc ca cc phn t, Nhng theo KEKUL : -Nguyn t cacbon c th kt hp vi nhau to thnh chui di v phc tp; -Ho tr cc nguyn t cacbon lun lun l bn; -Nghin cu cc sn phm phn ng c th cho bit thng tin v cu trc. Cu trc benzen l tc phm ni ting nht ca Kekul (1865) tng v cu to benzen n vi ng trong mt gic m.

Mt trong nhng nh ha hc ni bt nht ti Chu u t nhng nm 1850 cho n khi ng qua i, c bit l trong lnh vc l thuyt, ng l ngi sng lp chnh ca l thuyt c cu ha cht .

1829-1896

"cha ca nghnh cng nghip phn bn Ngi lm cho sinh vin AUGUST KEKUL b kin trc theo nghin cu ho hc

CTTQ

: k= 3( pi) + 1 (vng) =4 CnH2n - 6 n > 6

Ly (n- 6) C lm nhnh, di chuyn nhnh, b nhnh TD C8H10 CH2-CH3 CH3 CH3 CH3 CH3

CH3
CH3

CH3

CH2-CH3

C6H5 - CH3 Metylbenzen Phenylmetan TOLUEN

C6H5 CH2-CH3 Etylbenzen phenyletan

C6H5 CH CH3

CH3 isopropylbenzen 2-phenylpropan KUMEN

C6H5 CH2 CH2 CH3 propylbenzen 1-phenylpropan

-mch c hai nhnh tr ln: nh s C trn nhn sao cho: tng s s v tr nhnh l nh nht -chn mach chnh l nhn benzen hoc mch C h di nht

CH3 CH3

CH3

CH3

CH3
C6H4 (CH3)2 1,2-imetylbenzen

1,3-imetylbenzen

1,4-imetylbenzen

CH3

mch c hai nhnh trn nhn

-hai nhm th 2C k nhau:

s v tr 1,2= o (ortho)

-hai nhm th cch nhau 1 C : s v tr 1,3= m (meta) -hai nhm th cch nhau 2C : s v tr 1,4= p (para

CH3 CH3

CH3

CH3

CH3
C6H4 (CH3)2 1,2-imetylbenzen o-imetylbenzen o-xilen

1,3-imetylbenzen m-imetylbenzen m-xilen

1,4-imetylbenzen p-imetylbenzen p-xilen

CH3

CH2-CH2-CH3

CH2-CH3 CH3

C9H12
CH3 CH3 CH3 1,2,4-tri-metylbenzen

Propylbenzen CH3 CH-CH3

1-etyl-3-metylbenzen m-etyletylbenzen CH2-CH3

isopropylbenzen CH2-CH3 CH3 1-etyl-2-metylbenzen o-etyletylbenzen

CH3 1-etyl-4-metylbenzen p-etyletylbenzen

CH3

CH3 CH3
CH3 1,2,3-tri-metylbenzen

CH3

CH3

1,3,5-tri-metylbenzen

Benzen l mt du lng, khng mu, d bay hi v d chy, c mi thm ngt, c hi. khng ha tan trong nc, ha tan trong ethanol, ethyl ete, cloroform v cc dung mi hu c. si im 80,1 C im nng chy ca 5,533 C t nh la im 580 Celsius

+ Br2

Fe

Br
C6H5-Br Brombenzen phenylbromua

+ HBr

+ HNO3

H2SO4

NO2
C6H5-NO2 nitr benzen

+ H2 O

Nitration of Benzene

C ch HNO3+ C6H6

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

HNO3+ H2SO4

C ch HNO3+ C6H6

Quy lut th trn vng benzen

R R

y e Tnh cht nhm th -CxHy, amin: NH2 , R Ancol OH , Ete OR , X

nh hng mt e trn nhn

Ht e Axit -COOH, Este -COOR, Anhit -CHO,-NO2

kh nng phn ng th so vi benzen

nh hng v tr th trn nhn

Quy lut th trn vng benzen

O R N O

Tnh cht nhm th R

y e -CxHy, amin: NH2 , Ancol OH , Ete OR , X

Ht e Axit - C - OH, O Este -COOR, Anhit CH=O, -O=NO

Quy lut th trn vng benzen

R R

y e Tnh cht nhm th -CxHy, amin: NH2 , R Ancol OH , Ete OR , X

nh hng mt e trn nhn Lm tng d hn o,p

Ht e Axit -COOH, Este -COOR, Anhit -CHO,-NO2 Lm gim kh hn m

kh nng phn ng th so vi benzen

nh hng v tr th trn nhn

CH3

CH3

+ Br2

Fe 1:1

Br

+ HBr

o-CH3-C6H4-Br 2-Bromtoluen o-Bromtoluen CH3 Fe 1:1

+ HBr
Br

p-CH3-C6H4-Br 4-Bromtoluen p-Bromtoluen

CH3

H2SO4 HNO3 1:1

CH3 NO2 o-CH3-C6H4-NO2 2-nitrtoluen o-nitrtoluen CH3

+ H2 O

CH3

+ HNO3

H2SO4 1:1

+ H2 O
p-CH3-C6H4-NO2 NO2 4-nitr toluen p-nitr toluen

CH3 + 3HNO3 H2SO4 1:3

CH3 NO2 NO2 NO2 CH3-C6H2(NO2) 3 2,4,6-trinitrtoluen T.N.T

+ 3H2O

NO2 + 3HNO3 H2SO4 1:3

O2N

NO2

+ 3H2O

C6H3(NO2) 3 1,3,5-trinitrtoluen T.N.B

CH3

CH2

Cl

+ Cl2

nh sng 1:1
C6H5-CH2-Cl Benzyl clorua

+ HCl

CH2-CH2
CH2-CH3 as + Cl2 1:1

Cl + HCl

1-clo-2-phenyletan

Cl CH-CH3
+ HCl
1-clo-1-phenyletan

Benzen v ankylbenzen khng lm mt mu nc brm

Ni,to

+ 3 H2 CH3 + 3H2 Cl

C6H12 xiclohexan

Ni, to

CH3

C6H11CH3 metylxiclohexan

+ 3Cl2

nh sng

Cl Cl

Cl Cl

Cl C6H6Cl6 Hexacloxiclohexan Thuc tr su 6.6.6

Benzen khng tc dng KMnO4 Ankylbenzen khc , khi un nng, lm mt mu dd KMnO4

CH3

COOH

+ 3 [O]

KMnO4 to
C6H5COOH Axt benzoic

+ H2O

C6H5CH3 + 2 KMnO4 C6H5COOK + KOH +2 MnO2+ H2O

-3

-3 +1

+7

+3 -2-2+1

+4

C C + 6e +7 +4 Mn + 3e Mn

+3

CH2CH2-R

COOH

+ 5 [O]
-2 +1 -2 +1

KMnO4 to
+7

+ R-COOH + H2O
Axt benzoic

3 C6H5CH2 CH2-CH3 + 10 KMnO4 3 C6H5COOK +3 CH3-COOK + 4 KOH + 10 MnO2+ 4H2O

-2 +3 -2-2+1 +3 -2-2+1 +4

2C 2C +7 +4 Mn + 3e Mn

+3

+ 10e

CH2CH2-R

COOH

+ 5 [O]
-2 +1 -2 +1

KMnO4 to
+7

+ R-COOH + H2O
Axt benzoic

3 C6H5CH2 CH2-CH3 + 10 KMnO4 3 C6H5COOK +3 CH3-COOK +4 KOH + 10 MnO2+4 H2O C6H5CH2 CH2-CH3 + 2 KMnO4 +3 H2SO4 C6H5COOH + CH3-COOH + K2SO4 + 2 MnSO4+ 4 H2O 2C 2C +7 +2 Mn + 5e Mn
-2 +3 +3 +2 -2 -2 +7 +3 -2-2+1 +3 -2-2+1 +4

+3

+ 10e

Benzen c tm thy trong khng kh, nc v t.

Mt lng nh benzen ngoi tri: t khi thuc l,

cc trm dch v t, kh thi xe, v lng kh thi cng nghip. Benzen trong nh : khng kh c th cha benzen cao hn so vi khng kh ngoi tri t cc sn phm nh keo, sn, sp ni tht, v cht ty ra. Mt lng ln benzen gn cc trm kh t,

cht thi nguy hi hoc cc c s cng nghip.

Benzen l mt ha cht nguyn liu quan trng, ch yu dng sn xut styren , Cyclohexan, phenol, cumene, anilin, nitrobenzen v benzyl clorua . L nguyn liu chnh sn xut thuc tr su, nha tng hp, tng hp cht ty ra, thuc nhum

L dung mi cho sn v thuc tr

su.

Benzen cao hn mc bnh thng ti c s

s dng benzen, bao gm nh my lc du,

nh my dc phm, cc c s sn xut ha du, cc c s sn xut lp cao su, hoc trm xng. Cc cng nhn thp, my in, th giy, k thut

vin phng th nghim, hoc cu ha thng

phi tip xc benzen.

benzen c th nh hng th no n sc khe?

Th mc rt cao ca benzen c th dn n ci cht, trong khi mc cao c th gy bun ng, chng mt, nhp tim nhanh, nhc u, chn ng, hoang mang, v bt tnh. n hoc ung thc phm c cha cc cp cao ca benzen c th gy nn ma, kch ng ca d dy, chng mt, bun ng, co git, nhp tim nhanh, v cht.

Tc dng chnh ca vic tip xc

benzen di hn
Benzen gy tc hi v ty xng v c th gy ra s gim t bo mu dn n thiu mu. N cng c

th gy chy mu qu nhiu v c th nh hng

n h thng min dch, tng c hi nhim trng, gy ra bnh bch cu, c bit l bnh bch cu cp tnh gi l AML. y l mt bnh ung th

-chng ct du m v nha than - hir ankan, xicloankan CH3[CH2]4CH3 CH3[CH2]5CH3

Xt, to Xt, to

C6H6 + 4H2 C6H5CH3 + 4H2

-t benzen
C6H6 + CH2=CH2
Xt, to

C6H5CH2-CH3

C6H6 + R-Cl

AlCl3

C6H5-R + HCl