Nguyn Th Hng

Bng h thng phn hp cht Hyr - Cc bon

CnH2n + 2 - 2a ( n : S nguyn t Cc bon , a : S lin kt hoc s vng)
Loi
H-C

Cng
thc
chung
c
im
Cu to
Cch
c tn
ng
phn

H - C no
An kan ( Pa ra fin)
a=0
CnH2n + 2 ( n 1 )

An ken (Olefin)
a=1
CnH2n ( n 2 )

Lin kt gia cc nguyn t

l nhng l/k n (
)

Trong phn t c 1 lin kt

i ( 1 l/k
, 1 l/k
)

Trong phn t c 2 lin kt i

( 2 l/k
2 v tr khc nhau)

Gi theo s nguyn t C +
ui an

c tn cc AnKan tng ng
i ui an = en (hay ylen)
+ v tr ni i
- ng phn mch C
- ng phn v tr ni i

c tn cc AnKan tng ng i
ph m n = i en
+ v tr ni cc i
- ng phn mch C
- ng phn v tr ni i

E tan C2H4

Butaien - 1,4 C4H6

ng phn mch C
M tan CH4

Tnh
cht l
hc

Tnh

Cht

Ha

Hc

Hp cht
tiu
biu

H - C khng no
Ankaien ( i Olefin)
a=2
CnH2n - 2 ( n 3)

H-C-H

Trong phn t c 1 lin kt 3 ( 1

l/k
, 2 l/k
. 2 l/k
trn
cng 1 v tr)
c tn cc AnKan tng ng i
ui an = in + v tr ni ba

V tr, s v tn gc Ankyl
+ bnzen

- ng phn mch C
- ng phn v tr ni ba

- V tr gc ankyl trn vng

Benzen

E tin (Axetilen) C2H2

H-C=C-C=C-H

H-C=C-H
H H

H - C thm ( Aren )
ng ng ca Benzen
a=4
CnH2n - 6 ( n 6)

AnKin
a=2
CnH2n - 2 ( n 2)

Mch vng 6 cnh, c l/k

n xen l/k i

Ben zen C6H6

H-C=C-H

H H H H

H
S C1 C4 : Kh
S C5 C16 : lng
S C17 ln : Rn

S C2 C4 : Kh
S C5 C16 : lng
S C17 ln : Rn

1/ P th Halozen ( nh
sng)
CnH2n + 2+X2CnH2n + 1X+HCl
CnH2n + 1X+X2CnH2nX2 +HCl
..........................................
X2 : Cl2 hoc Br2 khan
2/ P tc dng bi nhit
a - P hy C v H2 (9000)
CnH2n + 2 nC + (n + 1)H2
b - P tch H2 (Fe , t0) Olefin
CnH2n + 2 CnH2n + H2
c - P b mch C (Crcking)
CnH2n + 2 CxH2x + 2 + CyH2y
x+y=n
3/ P Oxy ha hon ton

1/ P cng hp (H2,X2,HX,
H2O)
CnH2n + H2 CnH2n + 2
CnH2n + X2 CnH2n X2
CnH2n + HX CnH2n + 1X
CnH2n + H2O CnH2n + 1OH
Q.Tc: mccp nhi cp:
Phn t mang .tch
m gn vo C c s
Ng.T H t hn, phn t
mang . tch (+) gn
vo C Ng t H nhiu hn

3n + 1
O2
CnH2n + 2 +
2

nCO2 + (n + 1)H2O

nH2O > nCO2

nH2O - nCO2 = nH- C
xicloankan: L loi H - C no
mch vng => CT chung:
CnH2n (n 3 )
Tnh cht ha hc tng t
ankan: Tc dng vi Cl2 ,
O2 .....
Ring vi xicloankan c s

H2C = C - CH = C H2
CH3

lng
1/ P cng hp (H2,X2,HX, H2O)
( Cc P qua 2 giai on)
T 2 l/k i 1 l/k i ch c
l/k n
+H2

CnH2n - 2

CnH2n

Ni,t0

CH3- CH= CH2 + HBr

CH3- CH2- CH2Br

SP ph

2/ P trng hp
nCH = CH
R

R'

XT,t
P

- CH - CH R

R'

3/ P Oxyha
a. P oxyha khng hon ton
- Lm mt mu d2 KMnO4
3CnH2n + 2KMnO4 + 4H2O
3Cn H2n(OH)2 +2MnO2 +
2KOH
- C2H4 b oxiha nh

Ni,t0

CnH2n

+2

Lu : P g/ 1 ( t l 1 : 1)
1,2

CH2 = CH - CH = CH2 + Br2

1,4

CH2Br - CHBr - CH = CH2

CH2Br - CH = CH - CH2Br

2/ P trng hp
1,4

nCH2 = CH - CH = CH2

Na nc
1,2

CH3- CHBr- CH3

SP chnh

+H2

Cng h p v i H2
CnH2n - 2 + 2H2

Ni,t

Vis d : CH = CH + HCl
CH2 = CHCl + HCl

CH = CH2

3CH2OH- CHOH- CHOH- CH2OH + 8MnO2 + 8KOH

b. P oxyha hon ton- P chy

nCO2 + (n - 1)H2O

nCO2 > nH2O

CnH2n

Cng h p v i X2
CnH2n - 2 + 2X2

(- CH2 - CH -)n

+2

CnH2n - 2X4
CH2 = CHCl
CH3 - CHCl2

Cng h p v i H2O c HgSO4, 800c

to thnh An
ehit ho
c xeton
CH3CHO
C 2H 2 + H 2O
(CH3)2CO
C3H4 + H2O

2/ P trng hp
2CH =

CH

3CH =

C6H5Br + HBr

H2SO4

C6H6 + HNO3

C6H5NO2 + H2O

2)T/c H-C khng no- Cng

a. Cng Cl2 (as)
a/s

C6H6 + 3Cl2

C6H6Cl6

b. Cng H2
Ni , t0

C6H6 + 3H2

C6H12

B. T/c cc ng ng
1/ P th nhn
R

CH2 = CH - C = CH

- Br

C, 600

Fe,t0

1:1

HBr

C6H6

nCO2 + (n - 1)H2O

4/ P th kim loi

+ Br2

3/ P Oxyha- Lm mt mu
d2thuc tm
- P chy
3n -1
CnH2n - 2 + 2 O2

Fe , t0

C6H6 + Br2

CuCl/NH4Cl

CH

A. Tnh cht ca Benzen.

1) T/c H- C no - P th
a. Th Cl2 , Br2 khan
b. Th Nitro - NO2

Khi xt l pd Olefin

Cng h p v i axit

Vd : 3CH2 = CH- CH= CH2 + 4KMnO4 + 8H2O

3n -1
O2
2

1/ P cng hp (H2,X2,HX, H2O)

( Cc P qua 2 giai on)
T l/k ba1l/k ich cl/k
n

(- CH2- CH= CH- CH2-)n

Poli butaien 1,4 : Thnh phn

chnh ca cao su tng hp Buna
3/ P Oxyha
a. P oxyha khng hon ton
- Lm mt mu d2 KMnO4
(Ankaien b oxihoa ru no 4
chc)

CnH2n - 2 +

Benzen: cht lng, khng

mu, nh hn nc, o/ tan
trong nc

S C2 C4 : Kh
S C5 C16 : lng
S C17 ln : Rn

H2C = CH - CH = C H2 : Kh

Br

R
+ 3Br2

Fe,t0

- Br

Br

1:1

Br

tr
ng

3HBr

Nguyn Th Hng
C nh ( nh: C3H6, C4H8 ... ) khi
t/d vi Cl2, Br2 un nng th
xy ra p cng hp ph vng

CH3CHO

H2C

b. P oxyha hon ton- P

chy

CH2

t0

+ Br2

Br- CH2- CH2- CH2- Br

H2C

XicloPropan
brom etan

ng

1,3- i

CH4 + O2

No, t0

2C2H4 + O2

CnH2n

- Cht t
- CH4 iu ch C2H2 v
nhiu hp cht hu c quan
trng khc: CCl4 , CHCl3
,HCHO, CH3OH......
V d :
H - CHO + H2O

- iu ch Cc h/c Olefin

CuCl2/pdCl2

3n -1
O2
+
2

2CH3CHO

Ag- C =

C- Ag

2/ P th nhnh: Cl2,Br2
- CH3
+ Br2

+ H2O

kh

- CH2Br

a/s

HBr

Vng

C2H2

+ 2AgCl

nCO2 + n H2O

xt,t0.p

- ng dng quan trng l iu

ch cao su tng hp .
V d cao su Bu na (nh phn t/c )
Cao su Buna-S: nCH2= CH- CH= CH2 + nCH2= CH

CH3

CH3

C6H5

Stiren
xt,t0.p

(- CH2- CH= CH- CH2- CH2- CH- )n

( - CH2 - CH - )n

- iu cc loi ru, dn xut

Halozen, anehit, axit v l
nguyn liu iu ch nhiu
hp cht Polime khc

dng

NH3

C2H2 + Ag2O

Ag- C = C- Ag + HCl

nCO2 = nH2O
- Cht t
- iu ch cc loi cht do:
PoliEtilen (PE), PoliPropylen(PP)
...
V d:
nCH2= CH

Cc Ankin ni 3 u mch c k/n

t/gia p th kim loi

Cao su Buna-S

C6H5

Cao su Buna-N: nCH2= CH- CH= CH2 + nCH2= CH- CN

xt,t0.p

Nitrinacrilic

(-CH2- CH= CH- CH2- CH2- CH-)n

Cao su Buna-N

Cao su CloPren:
nCH2 = CCl - CH = CH2

xt,t .p

(- CH2 - CCl = CH- CH -)n

Cao su CloPren

CloPrren

Cao su IsoPren:
nCH2 = CCH3 - CH = CH2

CN

xt,t0.p

(- CH2 - CCH3 = CH - CH -)n

Cao su IsoPren

IsoPren

- iu ch : anehit axetc,
Xeton, axit hu c, cht t, s
l cy trng ........
- iu ch:Vinylaxetilen,
benzen,...

iu ch :
-Thuc s
u 666: HecxaCloXiclohecxan

xt,t0,p

nCH2 = CHCl
VinylClorua

(-CH2
PoliVinylClorua

V nhiu h/c hu c khc

CH3COO

CH-)n
Cl

CH3COOCH = CH2
CH3COO

xt,t ,p

nCH = CH2

CH3

CH3

iu chcht d o PVA
CH = CH + CH3COOH

+ H2O

- Thuc nTNT:(2,4,6-TriNitroToluen)

CH2 = CHCl

+ HCl

- NO2

H2SO4

+ HNO3

iu chcht d o PVC
CH = CH

C6H6Cl6

- NitroBenzen:

6000,C

3CH = CH
C6H6
- /ch cht do: PVC, PVA...

a/s

C6H6 + 3Cl2

- CH- CH2- n

H2SO4

3HNO3

O2N -

- NO2
+ 3H2O
NO2

- PoliStiren:
C6H6 + C2H2
nCH2 = CH

C6H5CH = CH2
CH2- CH

xt,t0,p

C6H5

C6H5

V nhiu h/c hu c khc

( PVA )

+ Phng php chung

- Cho d2 kim t/d mui KLK
ca axit cacboxilic
CaO ,t0

R- COONa + NaOH

iu

CH3COONa + NaOH

CnH2n

R - H + Na2CO3
0

CaO ,t

- Cho Olefin cng h p H2

CnH2n + H2

- Tch H2 t cc ankan

CH4 + Na2CO3
0

Ni , t

CnH2n

+ 2

- P2 ni mch
RX + 2Na + R'X
Vd:
CH3I + 2Na + C2H5I

ch

R-R
R - R' + 2NaX
R' - R,

ete khan

ete khan

CH3- CH3
CH3- C2H5 + 2NaI
C2H5- C2H5

- P2 Crcking
+ Phng php iu ch CH4
- Al4C3 t/d H2O hoc HCl
Al4C3

+ 12H2O

3CH4

Al(OH)3

Al4C3 + 12HCl 3CH4 +

4AlCl3
- Thu CH4 t kh thin nhin

Fe , t0

+ 2

CnH2n + H2

Fe , t0

C2H6

C2H4 + H2
- Tch H2O t ru no n chc
CnH2n

+ 1OH

C2H5OH

H2SO4
170

H2SO4
1700

CnH2n + H2O

C2H4 +

H2O

- Tch HX t dn xut
monoHalozen
CnH2n

C2H5Cl

1X

KOH/ROH

KOH / ROH

t ,xt

CH3- CH2- CH2- CH3

CH3- CH = CH- CH3

Al2O3 , 6500

CH2= CH - CH = CH2 + 2H2

CH2= CH - CH = CH2 + H2

+ Cc phng php iu ch
Butaien 1,3
- T C2H2
2C2H2

CuCl / NH4Cl

CH2= CH - C = CH

CH2= CH - C = CH + H2

Pd ,t0

CH2= CH - CH = CH2

- T ru etilc
2C2H5OH

CnH2n + HX

C2H4

+ Phng php chung: Tch H2 t

cc ankan hoc anken

HCl

* Khi tch H2O hay tch HX

phi tun theo qui tc
Zaixep
- Cho dn xut i Halozen t/d
vi Zn
CnH2nX2 + Zn CnH2n +
ZnX2
V d: C2H4Br2 + Zn C2H4 +
ZnBr2
- Phng php Crcking

MgO/Zn
5000

CH2= CH - CH = CH2 + 2H2O + H2

- T Butaniol - 2,3
CH3- CH - CH- CH3
OH OH

H2SO4
1700

CH2= CH - CH = CH2 + 2H2O

V nhiu h/c hu c khc

+ iu ch C2H2
- Cho t n ( Cc bua canxi)
t/d H2O
CaC2 + 2H2O C2H2 +
Ca(OH)2
( CaO

20000

3C

CaC2

CO )

- Nhit phn CH4

15000

2CH4

t K

H2

+ 3H2

30000c

C2H2

- T cc h/c ca axetilen
C2H2Br4

2Zn

C2H2

CH = C- Na + R-X

ho
c

pt, t0

C6H14

CH3

C6H6 + 4H2

pt, t0

C6H12

C6H6 + 3H2
CH3

pd,t0

3CH = CH

+ 3H2

3CH = C - CH3

C , 6000

C , 6000

CH3

CH3

+ 2ZnBr2

- iu ch ng ng ca
Axetilen
2CH = CH + 2Na

Vd:

- Trng hp Ankin

C2H2

- Tng hp trc tip:

2C

-Tch H2 t ankan hoc

Xicloankan

2CH = C - Na + H2
CH = C - R + NaX

CH3

- Phng php ni mch

C6H6 + R - X

AlCl3 khan

C6H6 + CH = CH2

C6H5 - R

AlCl3 khan

R
Ho
c: C6H5- COONa + NaOH

+ HX

C6H5 - CH - CH3

CaO
t0

C6H6 + Na2CO3