547.076
S460D
„
GS.TS. NGUYEN XUAN TRUONG
TT
f—^ I'—^
i
h 1^
CHuol
PHAN urnl
-JK
rn
r^i^*<n
r "1 M (
\f—
J
LJ LJ L_J
L_J
L_J LJ L_J L_J
I:
A
Giup
on tap he
thong hoa kien thiic
•
Giup
de nhd va nhd
nhanh kien thUc
•
Danh
cho hoc s""
• Danh cho hoc sinh Idp 10, 11, 12
• On thi tot nghiep
THPT
va luyen thi Dai Hoc
ODI
100
NHA
XOAT BAN
flAI
HOC QUOC
6IA
HA NOI
^lyctc
not
daii.
Hoa hoc la nganh khoa hoc nghifen
cihi
cac chat va su bien d6i cua cac
cha't.
Mu6'n
chuyen chat nay thanh chat khac ta cho cac chat tac dung vdi nhau
trong
nhOng
didu
kien nha't djnh
(xiic
tac, nhiet d6, ap
sua't,
).
Kifi'n
thiic
dirge torn tat ngan ggn
dudi
dang cac so do. Chu6i phan
ling
cung
giiip
ren luyen kha nang van dung kien
thiic,
chuSin bj t6't cho cac ki thi Tot nghidp Trung hgc ph6 thdng va Tuyen sinh Dai
hoc - Cao dang.
Xin
tran trgng
gidi
thieu cu6'n
sach:
SO
DO
CHUOl
PHAN
IfNG
HOA HOC
HCXJ
CO
Tac gia chan thanh cam on nhOng y kien dong gop cua ban dgc, nha't la
ciia
cac
Thay Co giao va cac em hgc sinh.
Tac
gid
goc hoa
tri
bang I09''28'.
•
Trong phan tir chi c6
lidn
kd't a nen nguyen tir C quay dugc dl dang quanh
true
lien
ket don C—C.
3.
linh chat vat h
•
d
didu
kien thuomg : C, ->
C4
la chat khi
C, ->
Ciftla
chat long
C|7
tro len la cha't ran
•
Khi so nguyen
tijr
C tang thi phSn tir
khoi
tang nen t" tang. Mach cacbon
cang phan nhanh thi be mat tid'p
+ CI: ) CH3CI + HCI
Metyl
clorua (clometan)
CH4 + 2C!2 >
CH2C1,
+ 2HC1
Metylen
clorua (diclometan)
CH4
+ 3CI, >
CHCI3
+
3HCI
Clorofom
(triclometan)
CH4
+
4CI2
CCI4
+
4HC!
Cacbon tetraclorua (tetraclo metan)
Cac d6ng phSn cua metan cung tham gia phan iJng
thfi'
tucmg
tir
metan.
Vf
du:
CI2,
lidt
n6n phan huy ankan thanh C va HF.
lot
qua y6'u n6n kh6ng phan
ting
vori
ankan.
•
Phan
umg
clo hoa va brom h6a xay ra theo co
ch6'
goc - day
truyln.
a)
Bir6c
khoi
mao :
cij-ci
—^ cr
+
cr
b)
Buorc phat
tri^n
day
truy^n
:
CHJIH
+
Phan ung
tiich
(gay
lien
ket C - C va C -H)
"^f
)
QH3^
+
C„_,H,(„_,),,
(m>2; n-m>0)
CH3CH2CH2CH3
500°C
>
xt
>
CH3CH
=
CHCH3
+
H2
CH3CH
=
CH2
+
CH4
CH2
=
CH2
+
doi
VI
ham
lirong
C va H trong X va Y nhu nhau nx <
ny
-> P, < P,
—.
, Mx iv 1
Mat
khac : mx = my -> Mx > My -» dx/y = =^ = > '
MY
Tir
bi^u
thiic:
^ = ^ va
dxA-
= — ta se
tinh
duoc ny do do
tinh
duoc % ankan
nx
Pi "x
bi
nhiet phan
+
Phan
umg
oxi
^'^"002)
h)
Oxi hoa khdng hodn todn
•
Neu khong du oxi, ankan chay khdng hoan toan, khi do ngoai CO2 va HjO
con
tao ra cac san ph^m nhu CO,
mu6i
than, khdng
nhiimg
lam giam nang
sua't
toa nhiet ma con gay doc hai cho m6i truomg.
•
Khi
CO
chat xuc tac, nhiet do
thich
hop, ankan bi oxi hoa khdng hoan toan tao
thanh dSn xua't
chiia
oxi.
Vi
du :
CH4
+ 0, ^" „ >
HCHO
+
H2O
our-j
a)
Khai
then-
ti( ddu mo, klii
thien
nhien
qua cue con dudng
crackinh
va chifng cat
phc'in
doan.
h) Phuon^
phdp
tdn^
mach
cachon
•
Tdnghop Vuydc(Phap)
2C„H„„ ,X + 2Na (C„H3„,+ 2NaX
Chu y: N6'u dung hai loai d3n
xua't
halogen c6 g6c ankyl khac nhau se thu
duoc h6n hop 3 ankan song kho tach khoi nhau vi chiing c6 nhi6t d6 s6i xa'p
XI
bang nhau:
R-R
+ 2NaX
R-R'
+ 2NaX
R'-R'
CH,(COONa),
+ 2NaOH —Sfi2_^ CH4 +
2NaX03
•
Phuong phap crackinh :
Q.^:
+
2 —ir2£]Hi2S—^
C,„H2„, + C,„.
„,,H2,„.
^,
+
2
(m > 2, n > m)
+ Phuong phap gift nguyen mach cacbon
•
Hidro hoa anken, ankin, ankadien tuong iJng :
QHi,,
+
HT
——>
C„H2„
+ 2
1°
C,iH2„
- 2
+ 2H2 ——>
QiH,,,
+
2
2. Tinh chat hoa hoc
a) Phdn
iOi}>
cgng md
vdni>
ci'ia
xiclopropan
vd .xiclohutan
^'
>
CH,-CH CH3
80° C
propan
+
Br2 CH2Br-CH2-CH2Br
/,.? -
dihrompropan
+
HBr ^ CH,-CH2-CH2Br
/
-
hiompropan
Xiclobutan chi c6ng vdi hidro :
Ni
120°C
>
CH,-CH2-CH2-CH3
Xicloankan vong 5, 6 canh tro len khdng c6 phan ting c6ng ma vong trong
nhirng
dieu ki^n trSn.
ti^'p tuf qua
trinh
chung
cat
ddu
mo,
xicloankan
con
diroc
didu
che'
tuf
ankan.
Vi
du
:
CH3[CH.]4CH,
) 11+ Hj
4.
iTng dung
Ngoai
viec
dung
lam
nhien
Vitu
nhu ankan, xicloankan dugc dung
lam
dung
m6i,
CHj — CH, CH,
H,C CH,
xiclopropan
B.
BAI TAP
CHu6l
PHAN
iTNG
Bai
1.
CHj
— CH,
xiclohutan
CH
—
CH3
metylxk 7 opropan
(6)
»
C3H5CI
(17)
(1)^
CH5OH
CH4(OH)3
•> Cao su Buna
»
CH
Huong
Akn
giai
CH,COONa
+
NaOH
^"^''^
>
CH4
+
Na.CO,
(3)
CH4
+ CI, >
CH3CI
+ HCl
(4)
2CH4
'-'"""^
>
QH,
+
2H,
(5) 2CH.,C1
+ 2Na CM, +
2NaCl
(6) C,H,
+
CI,
CH^Cl
+
HCl
(7) C,H4
>C,H4
(14) C,H,
+ H,0
Hg-'»4.so"c
^
CH3CHO
(15) C,H, +HC1 ->C,H,C1
(16)
C,H4
+H,
^'-'"^
) C,H,
(17)
C,H, >
C,H4
+ H,
(18) 2C,H, ^"4Ci.'oo"c ^
C4H4
(19) C4H4
+H,
P-'co3.'"c
^ c,H,
(20)
nC4H,
>
(C4He)„
(Cao
su buna)
(21) C4H4
+2H, >
CH4
+
4AIC1,
AI4C,
+
6H,S04
^ 3
CH4
+
2AU(S04),
.0
CH4
+ Na.CO, + H,0
4. C,H«
5. C + 2H3 -
6. CO, + 4H,
7. CO + 3H,
Cnickinh, l'
CH4
+ C,H,
.100^
c
>
CH4
vi
khuan
^
CH4 + 2H,0
^
CH4 + H,0
- - - ».
2)
C2H2
+ H.O
Jli^h^
CH,CHO
xo"c
3) CH,,CHO + H: C.H,OH
4) 2C,H,OH ^'^"^ >
C4H,
+ 2H,0+ H,t
45(rC
5)
C4H,
+ 2H, C4H,„
6)
C4H,o
C,H, + CH4
7) CH3-CH=CH, + HOH CH, -CH - CH3
OH
©
1) 2CH,COONa + 2H,0 ,
/^'^f'
^ ) C.H^+ 2C0, + NaOH + H,T
lamlanhnhanh . o .
2) C,He + CK
'"^"^"'^"^
) C,H,,C1
3) 2C2H5CI + 2Na ^ C,H,o +
2Naa
CH3-CH,-COOH
5) CH3 -CH -CH.
+
HCI
->CH3
-
CH-CH,^*
'
CI
6) CH3-CH-CH,+NaOH,„a„g CH3-CH-CH3
+
NaOH
OH
7) CH3-CH-CH3
+
CuO^ CH,-C-CH,
+ Cu + H.O
OH
Bai 4.
>
^
xt.
t"
>
^
xt.
t"
ankan
A
^
=
CH
CH,
+ 2H,
CH3
4)nCH2
=C-CH
=
CH2
CH.
5)
nCH3-CH-CH2
-CH,
xl.t"
, f
-CH,-C
=
CH-CH,-
CH3
de
hidro
^ /
CH,
CH3-C
=
CH-CH3^
CH,
12
Cty
TNHHMTVDVVHKhang
^
—•
clorofoni
—•
tetraclometan
b.
axitaxetic natriaxetat
—•
metan—^ metylciorua^^ etan—^ etilen
c.
butan —etan —etylclorua
—•
butan—• propen
—^
propan
Bai 6.
a) Cong
thirc
phan ti'r ciia hidrocacbon
A la
CiH,,
(vong). Hay viet PTHH cua
cac
phan
I'rng
theo chuoi
sau
dudi
dang cong thuc cau tao thu gon.
-
B
Mir
c
+D
b.CHd
A—B
^E—*^
F
c. C3H6—• A|
—• A2 —A3 —• A4
d. C3H,
-
e. C2H4Br2
C
B
B2
—•
Glixeron
E
• F
HjSO^d.t''
-CH-CH2-
I
CH2-OCOCH3
F
—•
CH4
—• H2
NaOOCCH2COONa
-£{j^"
E F ,_^„„ G • H •
pohme
_
B • E • G
(CjHftO)
k.
A
D
• F
H
(C2H6O)
Bai
8.
Viet PTHH ci'ia chuoi plian
irng
theo
sado
sau :
a.
CaC2
• A •
B
:— • D •
F
•
CH
<
A
—• C A ^
G
C,fl2,.
(n
>2)
2. Cdu tao
• Trong phan tir
c6
mot ndi doi
(C = C)
vdi
C
lai
hoa sp- tao goc 120",
phSng
trong
do c6 1
lien k^'t
a
b^n
va
mot lien
ket
7t kern b6n
nen
anken
dd
tham
gia phan
irng
hon ankan.
• Nguyen tir
ti
khd'i
hoi
nhd,
tinh
tan
trong
nirdc kem.
•
Cac
anken thirdng
phfln
cue
(|.i
^ 0) va fi,„ >
\i„,„„
do dd cac
ddng phan
trans
- anken ndng
chay
a
nhiet
dp cao
hon nhung
lai sdi d
nhiet
dd
tha'p hon
so
I'rng
cdng, phan
ihig
trung hop
va
phan
ting
oxi hda.
+
Phsin umg cong
a)
Cgni>
//.
—>
ankan
C„H2„
+
H,
— >
C„H2,n.2
Nlian
xet :
Khi giai toan
ciin
luu
y:
Goi
X la
hdn hop anken
va
C-H
-
+H.
C-H - ^, r
nank.n
pif = In
2
Pif = "umk - n,,„ '
Chi'i
y:
Khdng the' dung
each
nay neu cac
anken cdng
hop
vdi
H,
khdng cung
hieu
suat.
Sffcld
chuSiphan
li-ng
hda hpc Httu ca-
Nguyln
XuQn
Tru&ng
• Vi h6n hop X, Y c6 cung s6 mol C, H nSn d6't
chay
h6n hop A hay B d^u cho
h)
Cdna
halogen
(CI Br,)
cci.
^
C„H,„X3
C„H,„ + X, (dd)
Nhan
xet :
• Phan
ling
lam mA't mau dung djch brom dirge dung dl
nhan
bi6't cac hop
chait
chiJa
liSn ket doi, lien ket ba.
•
Khd'i
lugng ciia binh dung dung dich brom tang I6n la
khoi
luong ciia anken
Ih^p
thu.
• Neu bai toan cho m6t hay mot s6' hidrocacbon mach ho thuoc ciing day d6ng
dang tac dung voi brom theo ti le mol 1: 1 thi cac hidrocacbon do la anken.
c)
Cons
HA (A = halogen, OH", OSO,H")
lidn
ket 71 bj phan cue,
n6n ion duong dd gdn vao
cacbon
mang
didn
am va ngugc lai.
• Kha nang phan
ling
c6ng : HI > HBr > HCl > HF
• C6ng H,0 -> ancol
CH,=CH,
+ H3O '-^—^ CH.CH^OH
t"
' Ancbletylic
2CH,-Ci
l-CH,
+ 2H,0 —f^ CH3 - C H - CH3 + CH3-CH,-CH,OH
OH
Ancol
isopropylic Ancol propylic
(spchinh) (spphu) ,^
+
Phan
iimg
trung
hop
t", xt
-> [ -c - C - ]„
Vidu:
chay
mot hidrocacbon hay
nhidu
hidrocacbon thu6c cung day d6ng
dang thu duoc :
"CO2
= "H20
hoac
n^o^ = 1-5
n^^^Q
^ Cac hidrocacbon do thu6c day d6ng
dang anken hay xicloankan *
• D6't
chay
h6n hop ankan + anken (xicloankan) thi n^^Q^ > n^^o
lankan
= "H2O '
nc02
• Dot
chay
h6n hop anken + ankin (ankadien) thi n^.^^ >
n^^^Q
va
i) Oxi hda
khon^
hodn
toan
V Dung dich KMn04 loang a nhiet d6 thucmg oxi hoa noi d6i ciia anken thanh
1,2-
diol.
cacboxylic
hay CO, tuy
theo
CTCT
cua anken.
Phan
ling
nay
dugc
dung de' xac dinh vj tri cua n6'i d6i dua vao ca'u tao cua san
ph^m oxi hoa.
• Trong
cong
nghiep
ngirofi ta oxi hoa nhe etilen de san xua't
CH3CHO
2CH2
= CH3 + 0, ^^cx,,c.cx, ^
2CH3CHO
t°
+
Phan
ling the
• 6 nhiet d6 tha'p cac anken dl tham gia phan ling c6ng clo, nhimg b nhiet d6
cao (500 —
600°C)
m6t s6' anken dSu day d6ng ding c6 th^ tham gia phan
ling
the' boi do. Vi du :
CH,=CH-CH3
C„H3„„OH >
C„H,„
+ H,0
t^no'c
+
Cdn}> H2 vao ankin (xt: Pd) hoar ankadien (xt: Ni) tuang ifng
C„H,„_,
+ H3 —^
C„H3„
t°
Vi
du:
CHHCH
+ ^ CH,=CH,
t"
CH2=CH-CH=CH,
+ H, —^ CH3-CH,-CH=CH,
+
Crackinh ankan
+
Loai
HXra
khoi dan
xiidt
monohalogen cua ankan
tUcfng
ifng
C„H2„,
,X
'^Q";""-"'
CH, = C = CH2 propadien
(anlen)
• Lien kd't doi lien hgp: Hai lien ke't d6i b
each
nhau m6t lien ke't don. Vi du :
CH2=CH-CH=CH2 CH2=C(CH3)-CH=CH2
buta-1,3-dien
(butadien)
2- metylbuta - 1,3 - dien
(isopren)
'
• Lien ke't doi khong lien hgp: Hai lien ke't d6i
each
nhau nhieu lien ke't don.
Vfdu:
,234
5
CH2
= CH - CH2 - CH = CH2 penta - 1,4 - dien
3,
Butadien
va
isopren
a)
Tinh
chat vat li
- Butadien hay divinyl la chat khong mau, c6 mui dac trung, t° = - 4''C
- Isopren hay 2- metylbuta-1,3- dien la cha't long, kh6ng mau, s6i b
34°C
Deu la nhQng chat khdng tan trong
tao ra h6n hgp cac san phslm
c6ng-
1,2 va -1,4. 6 nhiet d6 tha'p uu tien tao ra
ra
san ph^m
cong
-1,2, nhiet d6 cao Uu tien tao ra san ph^m
c6ng
-1,4.
+
Phan i/ng trung hcq?
• Trung hgp — 1,4 d^ cho
polime
c6
tinh
dan h6i cao (cao su)
nCH,=CH-CH=CH2
—^'^"'"^
) [—CH2-CH=CH-CH2—]„
nCH2=C-CH
= CH2
CH,
p, t°, xt
polibutadien (cao su
buna)
-CH2-C
=
CH-CH2|-
CH3
poliisopren (cao su
h6i. Dieu
nay
iii>''
giai thich
tfnh
dan hoi kem
cm
m6t s6'
loai
cao
su
t6ng hap.
,
nCH,=CH-CH=CH,
p.
t°,
xt
-CH2-CH-
CH
=
CH.
5. Dieu
che
ankadien
+ Dieu clie'hiita
- 1J -
dien
a)
Dehidro
hoa
va AUO,)
2CH,CH,OH
MgOiA\,o,
^
CH,=CH-CH=CH,
+ H, +
2H.O
400-50(1"
C
c)
Di
tilf
axetilen
2CH^CH
_^ci/NH.ci
'•i^i—>
CH,=CH-C=CH
—^-^-^
CH,=CH-CH=CH,
d) T6ng hcrp
Konbe
(Due):
2CH,=CH-COONa
+
2H.O
—i^!^
CH,=CH-CH=CH,
+
2C0,T
+
:
C„H2„.2
(n>2)
2.
Cau tao
•
Trong phan
tijf
c6
lien
ke't
ba (C = C)
vdri nguyan tir
C
lai hoa
sp
nen
phan
tir
CO
ca'u
tao
thang,
goc
hoa
tri
180°.
0
•
D6
+
a)
tir
cacbon
(^^^^ =c =
3,29)
do do cac
ank
- 1 - in c6 H
linh
d6ng,
d^
bi
dut
d^
dong
vai tro tac
nhftn
trong phan ling
c6ng
hoSc
phan ling the'vdi
kim
loai.
Lien
ke't
ba (C = C) bao g6m 1
lien
ket
a va 2
•
('1
nhiet
d6
thircmg
: n = 2 ^ 4 la
chaft khi
''^ '
n
= 5->
16
la
chat long
n>
17 la
chat
ran
Cac ankin
ra't
ft
tan
trong nude,
tan
duoc trong
mot
so
dung
mdi
hihi
co.
thii
nha't
(anken)
ngoai
ti Id
mol
1: 1 c^
chu
y
dung cha't xiic
tac
thich
hop.
*
CHsCH
+ HV
Pd,
CH,=CH,!
CH^CH
+
2H.
Ni,
t°
CHj-CHj^
Nhan xet : Neu goi X la
h6n hop
ankin
va H,
ban
ddu,
mx
= mv va ny < nx -> Mv < My
d
(X/Y)
MY
"X
su
X, Y do 0
Cling
dieu kien
ap
sua't, nhiet
do) ^
CgnsX2(X=CI,
Br)
•
Phan ling
xay ra
qua hai
giai doan (giai doan
1
c6ng trans). Mud'n dtog phan
ting
a
giai doan
thii
nha't thi
cSn
thuc hien
a
ra qua hai
giai doan
va
giai doan
sau kho
hon giai doan tnr^
.
Sff
dd
chuSi
phan irng hda hpc
Hihi
cff
- Nguyen Xuitn
Trir&ng
CH.CH
+ HCl )
CH3=CHCI
—^
-CH2
-CH-
Cl
Vinyl
clorua
Poli(vinyl
clorua)
CH,
=
CHCl
+ HCl CH, -
(kh6ngb^n)
•
Cac d6ng dang + HjO Xeton
,,»,^„.,
, - A.I. . . i
R,-C=C-R,
+ HOH'
R, -CH = C-R2
OH
(khdng
bin)
R CH COR,
Nhan
xet Neu mot hidrocacbon tac dung v6i nude tao ra andehit axetic thi
hidrocacbon do la axetilen.
e)
Cong
axit
axetic
CH^CH
+
CH,COOH
^
CH,COOCH
=
CH,
xt,f
-CH2
-CH-
COOCH3
+
Phan
I'fng
the
hang
ion kim
loai
hoa tri I (Ag*, Cu*)
Nguyen
tiJ H
dinh
vao cacbon mang n6'i ba
linh
d6ng hem ra't
nhi^u
so
vdri
H
dinh
v^o cacbon mang nd'i d6i va nd'i dan, do do no c6 the' bi thay thd' bang
nguydn
tir kim
loai.
Nhu vay, chi c6 axetilen va cac ank -
1
- in
mdri
tac dung
diroc
vdi dung
R-C = CH +
AgNO,
+
NH3
R - C =
CAgi
+
NH4NO3
(mau
vang nhat)
CH
= CH +
2CuCl
+
2NH3
-> CuC =
CCui
+
2NH4CI
D6ng
(I) axetilenua (mau do)
R
-C = CH +
CuCl
+
NHj
-> R-C
=
CCui
+
cac phan
vrng
trfin
di nhan
bife't
axetilen va cac ank -
1-
in.
•
Axetilenua kim
loai
c6 th6'
duac
tach ra va phan
ling
vdi dung
dich
axit
thu
duac
axetilen
(diing
di tach cac chat ra
khoi
nhau)
Vi
du:
AgC = CAg + 2Ha -> CH = CH T +
2AgCli
•
I'mg
(hay)
C„H,„
_, + O: nCO, + (n —
1
)H30
Nhan
xet :
•
Neu bai toan cho dot chay mdt hay mdt sd hidrocacbon mach hd, thudc cung
day ddng dang thu
duac
:
"cOj
^"HJO
'^^^^ "Oj *^^'^"co2~^ hidrocacbon dd thudc day
ddng dang ankin hay ankadien va
"hh
=
nH20-"co2
^^^^
"hh
= 2(l,5nco2-^o^)
•
Dd't chay hdn hap ankan + ankin (ankadien)
hoac
anken + ankin (ankadien)
+
anken
-
n
H,0
va
n.
=
n
CO-
-n
h)
Oxi hoa khong hoan roan
Phan ung oxi hoa boi dung
dich
KMn04:
Tuong tu anken, ankin dl bi oxi hoa
bdi
KMn04
sinh ra cac san ph^m nhu
CO,,
HOOC
—
COOH,
3QH,
+
8KMn04
^
3KOOC
—
COOK
+
SMnO^i
dich
thu6'c tim di nhan
biet
cac ankin. So vdi anken thi t6c d6 phan utig
didn
ra cham hon.
5. Dieu che
+
Dieu che axetilen
a) Ti(
metan
: Phuomg
phap
chi'nh d^ di6u
ch6'
axetilen trong c6ng nghi6p
hifin
nay
la
nhiSt phan metan a
1500°C,
phan iJng thu nhiet manh.
1500°C
2CH4
h)
Tic than da, da v6i -> CaC, (dat den)
H,0
CH
Than
da
"^""^"""^
) CH,
di$n
' '
d) Tii muoi axetilenua
AgC
= CAg +
2HC1
->
CH
=
CHT
+
2AgCl^
CuC
= CCu +
2HCl
^
CH
s
CHT
+
2CuCli
+
Dieu chedong dang cua axetilen
a) Dehidio hoa ankan
ti/crng
I'/ng
'
Q,H2„
tang mach cacbon.
AgC=C-R+R'Cl
-> R'-C=C-R +
AgCli
,
Phan
ling
tuong
tir doi
v6i dSn xu^ chufa Cu
ciia
ankin.
B. BAI TAP
CHu6l
PHAN
UNG
Bai
1.
(NaOOC)2CH=CH
C2H5OH
n
C2H4Br2,
C2H,C1
QH|o
Hiro'ng
dan giai {
1.
NaOOC-CH=CH-COONa
+
2NaOH
+
2Mn02
+
2KOH
5.
nCH2=CH2-> [-CH2-CH2-],,
;
6.
C4H,o
'^^"''"'^
)
C2H,
+
C2H4
7. CH. + H,'
Ni.l"
-> C2H,
->C2H4
+
H2;
8.
CjHe
-
9.
CH4
+
H2O
. ,
C2H3OH
loang,
~ Nguyin
Xu&n
Trir&ng
Bai2.
1.
Ancol butylic ^ Butilen ^ Butan ^ MetanAxetilen
8
7 6
Etilen «- Brometilen <- Etilenglicol
<—
Etilen
2.
CH^ ^
CH4
^ CH,C\
C4H10
QH, \,
CHjCOONa QH4(OH),
3.
C3H6
\ -
brompropan
Propanol
- 2
3
(C,H,)„
4
5
1,2-
dibrompropan
+ Zn ->
C3H4
+ ZnBr,
©
1. 2CH,COONa + 2H,0
_J!E^
C2H,
+ 2CO. + 2NaOH + H^.T
2. CH6
—^CH4-i-
H,
3.
C3H4
+ 2KMn04 + 2H,0 ^
C3H4(OH)2
+
2MnO, + 2KOH
4. aH4 + HCI ^ C,H,C1
5. CH,C1 + 2 Na + C\-C.H, -> C4H,o + 2NaCl
6. C4H,o ^"^'^'"'^ > CH4 + C,H,
7. C,H, + [O] + H.O "^^""-^ ) C,H,(OH)3
©
1.
CH.,-CH=CH2
+ HBr ->
CH3
- C H -
CH3
Br
cry TNHHMTVDVVHKhang
CH,=CH-CH=CH,
>
C4H.Br4
Cao su
buna
Vinylaxetilen <— C^H,
Hirong dan giai
1.
HO-CHo-CH COONa + NaOH —!^ CHi-CH OH + Na.COj
2. 2QH,OH ^^i^CH,=CH-CH=CH, +
2H30
+ H,
3. CH,=CH-CH=CH, + Br,
-^CH,
-
CH
-
CH
= CH2
I
" I
Br
Br
^CH2-CH=CH-CH2
Br
Br
4. CH,=CH-CH=CH, + Br, ->• C H, - C H - C H - C
H2
""1^1 I I
Br
t' ^
Plivinyl
etilen
Tinh
bot
CH2=CH-COONa > CH2=CH-CH-CH2
C4H6Br2
Cho 3 san ph^m
-CH
- CH-
CH.Br CH,Br
3.
C3H,
-UC,H,
-^(C^H,)^
CI
-CH2
-C-CHj
CH3
Hiring dan
giai
O 1) (QHioOj),, + nH,0
nQH,A
2) QH,,0, > 2C,H,0H + 2CO,
3) 2QH5OH ^'2"3 ) CH,=CH-CH=CH, + 2H2O+ H^t
450"
c
4)nCH, =CH
I
,0p
2) CH, =C-CH^CH2 'l' > f-CH2-C = CH-CH2-'
3)
CH,
-CH2-C
= CH-CH2-
CH,
CH3
+
nHCl
CI
-CH2-C-CH2-CH2-
CH,
4) C,H,2
""-^'"^
) QH, + C,H,
5) nCH,-CH=CH, ^-CH-CH2-^
CH,
Bai
5.
dpdd
^
H,
< ! (COONa),
CH,=CH - C=CH
C.H,
Ag - CsC -Ag
CH,
- CHCl,
Hirang dan giai
0 O
^ CH = CH + 2HC1
10) CH = CH +
2HC1->
CH, - CHCl,
11) AgC ^ CAg + 2HCI -> CH = CH + 2AgCli
12)CH = CH
+Ag,0
->
AgC = CAg + H,0
Hoac
Viet:
CH = CH +
2f
AgCNHO^J^OH" AgC = CAg +
4NH3
+
2H2O
13)
2C2H,
14)
2CH4
Bai 6.
lilm
lanh nhanh LI i lO
> C.H2
+
3H2
1.
Tetrabrom axetilen —Axetilen —^ Andehit
axetic
—
CH,CHO
-> P.V.A
OH
I
5. CH C^CH-^
CH3-C-CH2
CH3-C-CH3 CH3-C-CH3
6. RBr,
-> C,H.
OH
A
—U B
OH
E^
O
-CH-CHo
Hirong
dan
giai
O
I) C2H4Br4 + 2Zn C,H, t + 2ZnBr2
2) CH^CH + H,0 )
CH3CHO
•
OU—OU
(
3)
CH,CHO+ ^O. -^^^CH.COOH
4)
Ca(OH)2
Hay
CO
the
vid't
CaC, + 2H" ->
C2H2
+ Ca-*
4)
C2H2
)
CH2=CH-C=CH
5)
CH2=CH-C=CH
+
H2
Pd
> CH,=CH-CH=CH,
Ni
-> CH3-CH,-CH=CH,
6)
CH2=CH-CH=CH2
+
H2
7)
CH3-CH2-CH=CH2
+ H. ^' >
C4H10
8)
C4H,o
7 )
HO-CH2-CH2-OH
+ 4[0] '''"'^""^ > HOOC-COOH +
2H2O
O
1)
C2H2
+
CH3COOH
—^
CH3-COOCH=H2
2)
nCH3-COOCH=CH2
-CH-CH2-
^0CbCH3
3)
CH3COOH
= CH, + NaOH CHjCOONa +
CH3CHO
4)
C2H2
+
H2O
^2lo"r
>CH3CHO
5) nCH^CH
Hay
(CH)2„
Ca
280"(•
4) QH,-CH CH, > QH,-CH=CH, + H,
5) QH,-CH= CH, -
-CH-CHj-^
6) QH, + H: CH,=CH:
Bal
7.
Hoan
thanh
so do
phan
urng sau :
606
CH,
(1)
-C2H2
(3)
C4H
4"4
(1) 2CH,
I5()()"c
lam
lanh
nhanh
C2H6
C2H4
Hirong dan
giai
-»-CH
= CH + 3H,
(2) 3CH^CH ^ )CH
CH2+H2
Pd/PdC03
>CH,^CH-CH=:CH.
(4) CH2 =CH-CH^CH2+2H2
>CH3-CH2-CH;-CH3
(5)
CH3-CH2-CH2-CH3-^5^^CH4+CH3-CH=CH2
Bai
9.
Vid't
phuomg
trinh hoa hoc cua cac
phan
urng trong chu6i bife'n h6a sau
(bifi't
A,
B, C, D, E, F la cac
hidrocacbon):
Hu-tfng
dan
giai
A:
CH:; B: QH,; C: C,H^- D: CH,; E: CH4
(I)
2CH,
I5i«)"c
,,
, , , , >CH sCH + 3H,
lam
lanh
phan
li^ng trong chu6i bie'n hoa sau (bie't
A,
B, C, D, E la cac
hidrocacbon):
C3H8
(1)
(8)
Hirong dan
giai
A:
CH4; B: C,H,: C ' .H,o; D: QH^; E:
CH4
33
(1)
CH,-CH^-CH^-CH^
"" >CH^+CH3-CH =CH^
(2)
CH^-CH=CH2+H2-^^^^CH3-CH2-CH3
(3) CH CH CH, >CH^+CH^=CH^
(4)
CH3-CH2-CH2
-CH3 )CH3-CH3+CH2 =CH2
•
(5)
CH3-CH3
""" >CH^CH + 2H3
(6)
CH^CH + H,
^'^"''^'^"^
>3CH^+4A1(0H)3
(2) 2CH,
'f'"'"^;
, >CH^CH + 3H2
^
lam
lanli
nhanli
2
(3) 2CH = CH-^^^CH^C-CH = CH2
(4)
CH^C-CH^CH,''^'^''^'^"3 >CH2 =CH-CH=CH2
J
(5)
CH2 - CH - CH = CH, + 2H2 )CH3 - CHj -
CH2
-
CH3
(6)
CH3 -CH, -CH2 -CH3 >CH3 -CH3 +CH2 =CH2
34
(7) CH2=CH2+H2 >CH3-CH3
(8)
CH3-CH3
>CH^CH
+ 2H2
(9)
CH =
CH
+ |02-^^2C02+H20
Bai 13. Hoan thanh chu6i bid'n d6i sau :
Metan A —^ B —^ C —^ polime
Huo'ng dan giai
AlaaH,,BlaCH,=CH-C=CH,Dla
CH2=CH-CH=CHohoSc
CH,=CH-CH(C1)=CH2.
Polime la
poll
(butadien)
hoSc
poll
(cloropren)
Bai 14. Hoan thanh chu6i bien d6i sau :
(X)
(hidrocacbon) (Y) -> etyl clorua. X, Y c6
the'
la Cha't n^o ? Hoan thanh
so do
phan
iJng tren.
35
Hirdnng
dan
giai
(X) (hidrcKacbon)
-> (Y) -> etyl
clorua
X
c6 the' la
C2H2
t6 C va H )
(A)
(2)
Axetilen
(1)
etan
\B)_(5)^
(D)'
Hirong
dan
giai
(1) HC=CH + 2H, ) QH^
(2)
HC^CH
+
(3) CH,=CH.+ H.
>
CH,=CH,
(4) 2C,H, ) CH3=CH-C^H
(5) CH,=CH-C=CH + 3H, "'""^ > CHj-CH^-CH^-CHj
(6)
CHj-CH CH CH,
''"''""^ > QH, + CH2=CH,
Bai 16.
Hoan
thanh
chu6i
phan
umg sau :
ALC
CHjQ,
+ HCl
>
QH, + 3H2
Cty
TnrHHUTTVTfvmiinang
rip
5 2CH,
c»cig.NH4Ci
^ cH,=CH-OCH
' • l(X)"C
6. CH,=CH-C^H
-K
H, '"'^''^ > CH,=CH-CH=CH,
7. nCH2=CH-CH=CH2 —^ ^H^-CH = CH-CH2>„ V J?0
8. CH,=CH—CH=CH, + 2H2
-»
CH3—CH,—CH,-<:H,
" *
t"c
Bai 17.
Hoan
thanh
chu6i
phan
umg sau :
C4H4
(3)
C,H
(5)'
3QH4
+
2KMn04
+ 4H:0 -> 3C,H4(OH), +
2MnO,
+ 2KOH
li
18.
Hoan
thianh
chu6i
phan
I'mg sau :
CsHgCI
HgCOONa
JIL CH. CH, JIU 11 Toluen TNI
•2"2
C2H6
p
- CloToluen
Sir
do
chudi
phan
liiif; hi'xi
hoc
UCni cir
-
NguySn
Xu&n
+
HCI
6. QH« +
CH3CI
>
QH,CH3
+ HCI
CH,
7.
+
3HNO3
H2S04d
CH, CH,
8.
o
+
cu
Fe,
t^C
o
CI
Bai
19.
Hoan thanh chu6i phan ung sau
:
CH,
NO2
+
3H2O
NO,
9
NO2
+
4H2-
, NO2
!
+
3H2O
Cty
TNHH MTVDVVH Khang
Vip
3. C,H,
+
CH,CI
^"^'•^•'"'^
)
C,H.,CH.,
+ HQ
CH.
CHoCI
4.
o
+
CI.
O
l"C
+
HCI
5.
CftH,CH,
^—
C,H,CI
I' .
CaC.
PVC
CoH
2114
7=^
C.H^Br
Hirong dan giai
1. CaC.
+2H.O
>
Ca(OH):
+
CH,
2.
C,H, +
2AgNO,
+
2NH3
> C,Ag, +
2NH4NO3
3.
C^Ag, +
2HC1
—>
C3H.
+
2AgCl
Trudmg
Bai 21. Hoan thanh chudi phan ung sau :
(2)
C6H6
(3)
C6H5CH3
C2H4
C2H6
(5)
C4H8
(6)
C4H10
Hirong dan giai
1. CaC, + 2H,0 > QHj + Ca(OH),
2. 3QH, "'-'"^ ) QH,
3. QHs +
CH3CI
> QH,CH, + HCl
4. CM. + H, '^'•'"^ > QH4
5.
2CH4
"g'^'^-'" ) H2C = CH-CH2-CH3
Ni.l"
6. CH3-CH2-CH = CH2 + H2
>CH3-CH2-CH2
7. C,H4 + H.
xl,t"C
Bai 22. Hoan thanh chu6i phan ung sau : (chu6i
hinh
vudng)
B: C4H8
C:
C4He
D: C4H10
Ni,t'
->
H3C
- CH2 - CH2 -
CH3
-II
* I
H2S04.
-»>H2C = CH-CH2-CH3
2. H2C=CH-CH2-CH3
^H2C = CH-CH =
CH2+H2
3. H2C = CH-CH=CH2+H2
Ni,l'
->H3C-CH2-CH2-CH3
4.
C4H
10
xt.t"C
^ C3H4 + CHe
i,
Bai 23. Hoan thanh chu6i phan
ting
sau : (chudi
hinh
con ca)
XI.
I*
->CH4+C3H,
I.
5. C2H,
>C2H2+2H2
16.
2CH4
>C2H2+3H.
Set ad
chuSiphdn
ihtg
hda
hgc Huu
<••'
\i-uyin XuSn Trurdrng
PItirang an 2
A
: C,H,
B:
C,H4
C:
C,Hs
D:
CH4
E:
CH4
F:
QH,
1. CH2=CH-CH3+H2-^^^^CH3-CH2-CH3
10
5. C.H^-^^qH.+qH,
6.
C2H,-^^C2H2+2H2
7. 3C,H,
XI,I'
->C.H,
Bai
25. Hoan thanh chu6i
phan
ling
sau :
an
6" 12
5
Butan
2 1
metan
*• A
B
PE
Viny!
axetilen —^ Poiibutadien
Polivinyl
etilen
Hirong dan giai
'1.
QH,o > QH, + CH4
2. 2CH,
15(X)''
Bai 26. Hoan thanh chu6i phan
ihig
sau :
CH4
4 • A<
lam
lanh
nhanh
^ C •^^^—• • D ^ » Cao SU
buna
F —-—• G —*• Polipropylen
Hiro'ng
dan
giai
(1)
2CH,
"^'11"'^
)
CH,
+
3H,
(2) CH^CH + H, > CH,=CH2
(3) nCH:=CH3 "•'"'P > l-CH CH J,,
(4) 2CH=CH C"<^''2-NH4Ci ^ CH=C-CH=CH,
1"
(5) CH=C-CH=CH, + H3 > CH,=CH-CH=CH2
(6) nCH,=CH-CH=CH,
—"-'"'P
> f-CH2-CH=CH-CHHn
(7) CH=C-CH=CiI, +3H, > CH.CH.CH^CHj
Trircmg hop 1. C.H.Br4 -> QH, -> QHe, ^
C2H5CI
-»
C2H4
Polietilen
C2H2Br4
+ 2Zn ^ QH,
+2ZnBr2
CH2+H, > C,H, % ^'^v
QHft
+ a, CHjCl + HCl
QHsQ
—^ CH4 + HCl
nCH,=CH,
^2^^4^-'"
) [-CH CH,-],,
Trircfng hop 2. C,H:Br4 CjH, CjHiCl
->• C2H5CI
C,H4 -> Polietilen
C2H3Br4
+ 2Zn C^H.
+2ZnBr2
C^H,
+ HCl > C,H,C1
C.H,C1 + H, >
C.HsQ
QH^Cl C.H4 + HCl
nCH.=CH, y [-CH3-CH2-L
Truofng hop 3.
CH,Br4 -» CH:
'^'i".!!'^
> QH, +
3H,
C,H, +2H2
> QH, -^.^
TrircJng
ho'p 2.
C^HT
—*•
C4H4
—•
C4H10
—•
QjH^
2CH=CH
Cua^.NH^a ^ CH=C-CH=CH,
CHsC-CH=CH,
+3H, > CH.CH^CHjCH,
CH,CH,CH,CH,
"""'"'"'^
)
QHfi
+
CH2=CH,
Trircyiig
hop 3. CH^COONa ^
CH4
C,H, ^ CjH,
CHjCOONa
+ NaOH ) CH4 + Na.COj
KIEN
THirc CO BAN j
I,
HIDROCACBON
THOM
(AREN)
Cong
thurc
Chung
:
C„H2n-6
(n>6)
Cau
true
cua
phan
tilr
benzen
•
Sir hinh thaiih
lien
ket trong phSn tir
benzen
Sau nguydn
tiJf
C trong
phan
tir
benzen
a trang thai lai hoa sp' (lai hoa tarn giac).
Sau nguyen tir C trong
phfin
tir
benzen
tao thanh mot luc
giac
diu. Ca 6 nguyen
tir
C va 6 nguyen tir H ciing nJm tren mot mat phing (con goi la mat
phSng
phan
tir).
Cac goc hoa tri deu
bang
120".
•
Bieu di6n cau tao ciia
benzen
hoac
3.
Tinh
chat
vat h'
Benzen va cac ankyl
benzen
la nhihig
chat
khong mau, hdu nhu kh6ng tan trong
nu6c
nhutig tan nhieu trong cac dung moi
oj
Phan i'fn)j
halogen
hoa
•
Benzen va cac dong
dang
ciia
benzen
khong
phan
ii'ng
v6i dung djch brom
nhung
phan
ii'ng
d6
dang
vdi brom khan khi c6 mat cOa bot sat lam
xiic
tac
Br
Br^
Fe
+
HBr
Brombenzen
47
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