Hintedo sơ đồ chuỗi phản ứng hóa học hữu cơ
Bạn đang xem bản rút gọn của tài liệu. Xem và tải ngay bản đầy đủ của tài liệu tại đây (17.63 MB, 40 trang )
547.076
GS.TS. NGUYEN X U A N T R U O N G
S460D „
TT
f—^
i
CHuol P H A N
-JK
rn
I'—^
h
1^
urnl
r^i^*
M(
\f—
J L J L J L_J L_J L_J L J 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
"
"
6ntMtotn,M
||||||||||i|i|||i|
iL
)
•
DVL.013452
O
NHA XUAT
BAN flAI HOC QUI
sa DO
^4
I..'
CHUOl PHAH UTHG
WOA HOC
Hiivco
•
A
•
•
•
Hl'i'r
Giup on tap he thong hoa kieh thtic
Giup di nhd va nhd nhanh kieh thiic
Danh cho hoc sinh Idp 10, 11, 12
On thi tot nghiep THPT va luyen thi Dai Hoc
\
-
• - •••
'1
100
ODI
NHA XOAT BAN
flAI HOC QUOC 6 I A HA NOI
*
T 6 M TAT KIEN THQC CO B A N
vA BAI TAP C H U O I P H A N Q N G
^lyctc not
HIDROCACBON
daii.
HIDROCACBON
ChU(mgl.
Hoa hoc la nganh khoa hoc nghifen cihi
cac chat va su bien d6i cua cac
A. K I E N THirC C O BAN
cha't. Mu6'n chuyen chat nay thanh chat khac ta cho cac chat tac dung vdi nhau
I. H I D R O C A C B O N NO, M A C H Hd (ANKAN)
trong nhOng didu kien nha't djnh (xiic tac, nhiet d6, ap sua't, ...).
1. Cong thiic Chung: C„H2„,2
Kifi'n thiic hoa hoc chij yfe'u la kife'n thiic ve sir tuong tac giOa cac chSft xay ra
trong phan ting hoa hoc va dugc diln ta bang phuong trinh hoa hoc.
2. Ca'u tao
•
Nguyfin tir C trong phan tir ankan d^u d trang thdi lai hoa sp' (cacbon tii:
dian), goc hoa tri bang I09''28'.
•
Trong phan tir chi c6 lidn kd't a nen nguyen tir C quay dugc d l dang quanh
true lien ket don C—C.
Chu6i phan ling giiip cac em 6n tap, he thC'ng hoa kien thiic mdt each sinh
d6ng va hieu qua nha't.
Chudi phan ling giiip d l nhor, nhd lau boi kie'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
(n > 1)
3. linh chat vat h
•
d didu kien thuomg : C, -> C 4 la chat khi
C, -> Ciftla chat long
C|7 tro len la cha't ran
hoc - Cao dang.
Xin tran trgng gidi thieu cu6'n sach:
•
SO DO C H U O l PHAN IfNG HOA HOC H C X J C O
Khi so nguyen tijr C tang thi phSn tir khoi tang nen t" tang. Mach cacbon
cang phan nhanh thi be mat tid'p xiic cang giam nen lire hut giua cac phan tix
Tac gia chan thanh cam on nhOng y kien dong gop cua ban dgc, nha't la ciia cac
giam nen t" giam.
Thay Co giao va cac em hgc sinh.
•
Tac gid
V i khong c6 lien ket hidro vdi nude ndn tat ca hidrocacbon no deu khdng tan
trong nude (ki nude) nhung tan nhieu trong dung moi huti co.
4. Tinh chat hoa hoc
+ Phan umg the halogen
^
C,|Hi|, ^. 3 +
ZXT
— — ^
C„H2„ + 2—
Vi (III:
CH4 + CI:
CH3CI + HCI
)
Metyl clorua (clometan)
CH4 + 2C!2
> CH2C1, + 2HC1
Metylen clorua (diclometan)
CH4 + 3 C I ,
>
CHCI3 + 3HCI
Clorofom (triclometan)
CH4 + 4CI2
CCI4 + 4 H C !
Cacbon tetraclorua (tetraclo metan)
Cac d6ng phSn cua metan cung tham gia phan iJng thfi' tucmg tir metan. Vf du:
CI2, as
25° C
—.
,
Mx
iv
1
Mat khac : mx = my -> Mx > My - » dx/y = = ^ =
> '
MY
CHj-CHa-CHj + CHj-CHj-CH.a + HQ
Tir bi^u thiic: ^
2 — clopropan (57%) 1 — clopropan (43%)
CH3-CH2-CH3
2a^iL_^ CH3-CHBr-CH,
+ CHj-CH.-CH^Br + HBr
25°C
2-brompropan (97%) 1 - brompropan (3%)
(san phim chinh)
(san ph^m phu)
• Q o the' cho H a cacbon cac bac khac nhau. Brom hdu nhu chi the' cho H d
cacbon bac cao. Flo phan ling manh 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
C„H2„,2
W ^ M ; C H 4 + 202
Y
^
CH31
...
C02
"hh
=2(no2-
^ ' ^ " 0 0 2 )
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
CH3-CH3
sua't toa nhiet ma con gay doc hai cho m6i truomg.
•
+ Phan ung tiich (gay lien ket C - C va C -H)
) QH3^ + C „ _ , H , ( „ _ , ) , ,
>
500°C
xt
(m>2;
CH3CH = CHCH3 + H2
CH2 = CH2 + CH3CH3
Khi C O chat xuc tac, nhiet do thich hop, ankan bi oxi hoa khdng hoan toan tao
thanh dSn xua't chiia oxi. Vi du :
n-m>0)
CH4 + 0 ,
CH3CH = CH2 + CH4
>
^" „
Dudri tac dung cua nhidt va xuc tac
Fe, Pt, ...), cac ankan kh6ng
nhOng bi tach hidro tao thanh hidrocacbon khCng no ma con bj gay cac li6n
k6't C - C d^ tao ra cac phan tir nho hem.
•
Ne'u mach cacbon dai, khi oxi hoa c6 the' bi be gay :
CHiCH,CH,CH3 + O,
+ Phan umg phan huy
• Phan hiiy boi nhiet:
Gia sir ta c6 so d6 :
1 ()()()" c
crackinh
-> honh(?pY
DSc biet:
Trong phan umg crackinh s6 mol khi sau phan umg tSng nhimg kh6'i liromg kh6ng
doi VI ham lirong C va H trong X va Y nhu nhau
nx < n y -> P, < P,
> HCHO + H2O
200atni.300"C
Nhdn xet:
khi khac
^
< " H 2 0
"hh = " H J O - " C O 2
Cl' + Cr ^ CI.
•CH3 + a * ^ CH3C1
ankan
+ 2H,0
-> Cac hidrocacbon do thu6c day dong ding ankan va
c) Bixorc dut day truy^n
Hon hdp X
nC02 + (n + DH.O
^-
Hoac : no2 > l.Sncoj
CH3C1 + cr
CH3CH2CH2CH3
+
d6ng dang ma thu duoc :
"CO2
•CH3 + CI -f CI
"^f
"x
Nhdn xet: Khi d6't chay m6t hay m6t h6n hop cac hidrocacbon thu6c ciing day
C H J I H + CI* - ) • 'CHi + HCl
•CH3 + *CH3
Pi
bi nhiet phan
+ Phan umg oxi hoa
a) Oxi hoa hodn toan
Khi dd't cac ankan chay tao ra CO,, H-,0 va toa nhilu nhiet
b) Buorc phat tri^n day truy^n :
H + CI* ^
va dxA- = — ta se tinh duoc ny do do tinh duoc % ankan
=^
nx
' " ' I > 2CH3COOH + H , 0
our-j
•
PhSn huy bai clo :
+
C„H„,.3 + (n H- DCU
,„Hs.C^,c.rn,
>
+ 2(n +
DHQ
AUCj+
5. D i e u c h e
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
•
Mot so phmmg phap khac
a) Tif nhom cachiia :
I2H2O
(Di^u chd-AI4C, : 2AI2O3 + 9C
h) Ti(C vdH.
C + 2H.
cachon
4 A l ( O H ) 3 i + 3CH4
) Al^Q + 6C0T)
:
Ni
^
CH4
. .TOOT
Tdnghop Vuydc(Phap)
2C„H„„ ,X + 2Na
II. H I D R O C A C B O N NO, M A C H V O N G ( X I C L O A N K A N )
( C „ H 3 „ , + 2NaX
C„H2„
J. Cong thitc chung:
(n>3)
Chu y: N6'u dung hai loai d3n xua't halogen c6 g6c ankyl khac nhau se thu
2. Tinh chat hoa hoc
duoc h6n hop 3 ankan song kho tach khoi nhau vi chiing c6 nhi6t d6 s6i xa'p
a) Phdn iOi}> cgng md vdni> ci'ia xiclopropan
vd
.xiclohutan
X I bang nhau:
R-R
R X + R ' X + 2Na
•
+ 2NaX
^'
R-R'
+ 2NaX
R'-R'
+ 2NaX
propan
+ Br2
CH2Br-CH2-CH2Br
T6ng hop Konbe (Dure)
/,.? -
2 R C O O N a + 2 H . O -^2!^
R - R + 2CO,t +
c) Phuang phdp gidm much
/ -
Catot
Ni
Phuong phap Duma :
120°C
R
H
+ Na^COj
C H , C O O N a + NaOH
—
CaO
C
H
4
+ Na,COi
t'
t"
Xicloankan vong 5, 6 canh tro len khdng c6 phan ting c6ng ma vong trong
h) Phdn I'rng the
Phan ling thd' a xicloankan tuong tu nhu a ankan. V i du :
a
CaO
C H , ( C O O N a ) , + 2NaOH — S f i 2 _ ^ CH4 + 2 N a X 0 3
+ Ch
Phuong phap crackinh :
+ HC1
—
Q.^:.. + 2 — i r 2 £ ] H i 2 S — ^ C,„H2„, + C,„. „,,H2,„. ^, + 2 (m > 2, n > m)
+
> CH,-CH2-CH2-CH3
nhirng dieu ki^n trSn.
Vidu:
•
hiompropan
Xiclobutan chi c6ng vdi hidro :
cachon
R C O O N a + NaOH —
dihrompropan
+ HBr ^ C H , - C H 2 - C H 2 B r
2NaOH + H . t
Anot
•
> CH,-CH.-CH3
80° C
xiclopentan
Phuong phap gift nguyen mach cacbon
•
QHi,, + HT
——> C„H2„ + 2
C,iH2„ - 2 + 2H2
——> QiH,,, + 2
>
(•) Phdn I'fng oxi hoa hodn todn
C„H2„+y02
D i tir ancol no, dcm chiic :
C „ H 2 , „ , O H + 2HI —
\ HCi
xiclohexan
1°
•
+ CU
Hidro hoa anken, ankin, ankadien tuong iJng :
C„H2„,2 + H2O + I2
C6H,2+ 9O2 ^
nCO. + nH20
6CO2 + 6H2O
3.
»i6uche
E l a : CH,CHO
Ngoai viec tach trirc ti^'p tuf qua trinh chung cat ddu mo, xicloankan con diroc
didu che' tuf ankan. V i du :
F la: Q H 4
G la: C 4 H ,
H la: C a C
)
CH3[CH.]4CH,
1
1
+
Hj
Cac phirong trinh hoa hoc :
4. iTng dung
(1) A I 4 C , + 1 2 H , 0 ^ 4 A 1 ( 0 H ) ,
+3CH4
Ngoai viec dung lam nhien Vitu nhu ankan, xicloankan dugc dung lam dung
t", xt
xiclohexan
5. Cdch viet dong phdn mach
o
+
benzen
vdng
Ve vong 16n nha't roi thu nho dan, chii y t6 hop cac loai nhanh (neu c6).
•
Them cac nguyen t\X H vao mach de dam bao dung hoa tri I V ciia cacbon.
H,C
CH,
xiclopropan
(3)
C H 4 + CI,
CHj — CH,
CH,
C H — CH3
CHj — C H ,
metylxk 7 opropan
xiclohutan
(4)
2CH4
(5)
2CH.,C1 + 2Na
(6)
C,H, + C I ,
(7)
C , H 4 + H C 1 ->C,H,C1
(8)
C , H 4 + Br,
(9)
C,H4 + H,0
(11) CaC, + H , 0
Bai 1.
(6)
C,H4Br,
CjHsOH
CH4(OH)3
C , H , + Ca{OH),
> C,H6
>C,H4
'''^^"-^
•> Cao su Buna
Hg-'»4.so"c ^ C H 3 C H O
(15) C,H, + H C 1 ->C,H,C1
(16) C , H 4 + H ,
(17) C , H ,
(18) 2 C , H ,
^"4Ci.'oo"c
(20) nC4H,
(21) C4H4 + 2 H ,
(22) C4H,o
^'-'"^ ) C , H ,
> C,H4 + H,
(19) C4H4 + H ,
» C4^10
H
3C,H4(OH), + 2 K 0 H + 2MnO,
(1)^
CH5OH
la: A I 4 C ,
CH^Cl + HCl
C3H5CI
(14) C,H, + H , 0
Huong Akn giai
CM, + 2NaCl
(12) C,H, + 2 H ,
»
(13) C , H , + H ,
(17)
A
+ HCl
'-'"""^ > Q H , + 2 H ,
(10) 3 C , H 4 + 2 K M n 0 4 + 4 H 2 O
B. B A I T A P C H u 6 l P H A N iTNG
Dap an
> CH3CI
3H.
•
CH,
^"^''^ > CH4 + Na.CO,
(2) CH,COONa + N a O H
m 6 i , lam nguydn lieu di^u chfi'cac chat khac.
^ C4H4
P-'co3.'"c ^ c , H ,
> (C4He)„ (Cao su buna)
> C4H,o
' " " " ^ C H 4 + C,He
B la: CH.COONa
D la: Q H j
8
9
Bai 2.
Bai 3.
1. CH4 - U C , H . — . C H , C H O ^ C , H , O H ^ C 4 H , - ^ C 4 H | o
Ancol iso-propylic<-
—^C4H|o—^CH4-^ H C H O
- l ^ C H ^ — • CiH^Cl —^C4H|o—^CH4It
CO,
2. CH,COONa
3. Q H ^ C l — ^ C , H , O H
QH,
O
1) 2CH4
C,H,
^C,H,0 -^CH,-CH.-COOH
.:
,,
,
) C H , + 3H,
lam lann nhann
2) C2H2 + H.O
-
Jli^h^
-
-
».
CH,CHO
xo"c
Hirdng dan giai
1. N a - O - C - C H , - C - N a
II
II
o
r
o
A I 4 C , + 12HC1
CH4 + 2Na,CO,
Cnickinh,
5. C + 2H3
6. CO, + 4 H ,
-
.100^ c
C.H,OH
^'^"^ > C4H, + 2 H , 0 + H , t
45(rC
CH4 + Na.CO, + H , 0
5) C4H, + 2 H ,
C4H,„
6) C4H,o
C , H , + CH4
3 CH4 + 4A1 ( O H ) ,
3 CH4 + 4AIC1,
A I 4 C , + 6H,S04 ^ 3 CH4 + 2AU(S04),
4. C,H«
3) CH,,CHO + H :
4) 2 C , H , O H
OiO. t0
2. C H , C O O H + 2NaOH
3. A I 4 C , + I 2 H 3 O ^
+ 2NaOH ^
.0
l'
>
vi k h u a n
7. CO + 3 H ,
C H , - C H - CH3
CH4 + C , H ,
,
/^'^f'
^ ) C.H^+
lamlanhnhanh
^ CH4 + 2 H , 0
^
OH
© 1) 2CH,COONa + 2 H , 0
CH4
CH4 + H , 0
0
8. CH,COONa + NaOH
7) C H 3 - C H = C H , + H O H
> CH4 + Na^CO,
2) C,He + CK
'"^"^"'^"^
3) 2C2H5CI + 2Na ^
4) C4H,o
)
.
o
C,H,,C1
C,H,o + 2 N a a
"''^'"^ > C , H , + CH4
5) CH4 + 0 ,
) HCHO + H , 0
600" c
6()()"C
6) H C H O + 2 A g O
> CO, + H^O + 4Ag>l.
© 1) C3H7CI + NaOH,„j„g — ^ CiH^OH + NaCl
2C0, +
.
NaOH + H,T
Cty TNHHMTVDVVHKhang
2) C,H70H + CuO —
Vift
^ C H 3 - C H 2 - C H O + Cu + H3O
1 ^
Mn"
3) C H , - C H , - C H O + - O ,
2 "
XI,t
6) n C H , - C = C H
>CH3-CH,-COOH
I
^
/
CH3
I
CH3 CH3
-C-CHI
4) C H , - C H 2 - C H O + ^ O .
> CH3-CH,-COOH
5) CH3 - C H - C H . + H C I - > C H 3 - C H - C H , ^ *
C H 3 J„
(Bai 5, 6, 7, 8 ban doc tir viet P T H H ciia cac phan urng)
'
Bai 5. Viet P T H H cua cac pu thirc hien chuoi bien hoa sau :
CI
6) CH3-CH-CH,+NaOH,„a„g
a. A I 2 O 3 — • A I 4 C 3 — • m e t a n — > • m e t y l c i o r u a — • metilenclorua
CH3-CH-CH3
+ NaOH
— •
OH
7) C H 3 - C H - C H 3
clorofoni — •
b. axitaxetic
+ C u O ^ C H , - C - C H , + Cu + H . O
tetraclometan
natriaxetat — • m e t a n — ^ m e t y l c i o r u a ^ ^ e t a n — ^ etilen
c. butan — e t a n
OH
^
— e t y l c l o r u a — • b u t a n — • propen — ^ propan
Bai 6.
Bai 4.
a) Cong thirc phan ti'r ciia hidrocacbon A la CiH,, (vong). Hay viet P T H H cua cac
phan I'rng theo chuoi sau dudi dang cong thuc cau tao thu gon.
>
B
^
D
»
E
>
^ xt. t"
ankan A
5
>
Polipropilen
-
+CuO
+NaOH
B
+0,
D
^ — E
b) Dung cong thuc cau tao viet PTHH ciia cac phan irng theo so d6 sau :
cao su isopren
i-Br-,
" CH,
I
-C - C H -
QH,o
—<
"
- C4H6Br2
D
C4H6Br-,
("i9t chat)
(hai chat)
Hwong dan giai
DCjH,,
) C,He+
2) n C H 3 - C H = C H . -
XI.I"
Bai 7. Hoan thanh cac chu6i phan irng sau :
C,H,
a. A
. f-CH-CH2-
Mir
B
+D
c
-CH-CH2I
CH2-OCOCH3
CH.
3)nCH3-CH-CH2-CH3
> r C H 2 = C - C H = CH
xl.t"
,
f-CH,-C = CH-CH,-
5) n C H 3 - C H - C H 2 - C H ,
12
^ E — * ^
de hidro
^ /
c. C 3 H 6 — •
d. C 3 H ,
CH3
CH.
CH,
A — B
b.CHd
CH3
CH,
4)nCH2 = C - C H = CH2
+ 2H,
A | — • A2 — A 3 — • A4
-
B2
C
CH3-C = CH-CH3^
CH,
F — • CH4
F
— •
Glixeron
E
•
e. C2H4Br2
B
HjSO^d.t''
F
— •
H2
NaOOCCH2COONa
-£{j^" (-1'""! pluin
g.
.
C3H6
, ,
• ,
irnfi hoa hoc HiTii cir - I\'f>uypn \tiiiii
—
•
_^
C,
—
•
NaOHIg
E
_
—
•
C H 3 - C O - C H O
^ AgNO^/NH,
2^A - 2 — B
h . 1.1 i c l o | * o p a n
•
C2
Trir&ng
F
B
•
D
•
,_^„„
E
•
„
H2SO4
—-—
G
•
G
(CjHftO)
H
(C2H6O)
C h u o n g 2.
+CI2
D — •
H
•
pohme
A. K I E N T H t r c C O B A N
1. A n k e n (olefin)
/. Cong thifc Chung :
2. Cdu tao
•
k. A
F
•
A
•
B: —
•
C,fl2,.
(n >2)
T r o n g phan tir c 6 m o t n d i d o i ( C = C ) v d i C l a i h o a sp- t a o g o c 120", phSng
t r o n g d o c 6 1 l i e n k^'t a b^n v a m o t l i e n k e t 7t k e r n b6n n e n a n k e n d d t h a m
g i a p h a n irng h o n a n k a n .
Bai 8. V i e t P T H H ci'ia c h u o i p l i a n i r n g t he o s a d o sau :
a. CaC2
HIDROCACBON KHONG NO
•
D
• F
•
N g u y e n tir C k h o n g q u a y diroc q u a n h l i a n ket d d i ( C = C ) l a m xuS't h i e n d d n g
CH
phan k h o n g g i a n ( d d n g phdn cis.
trans).
3. Tinh chat vat li
<
A —•C
+HC1^
B i v ^BN a O H
c. CH4 — • A - • < ^
+2HCI^ B 7
J^—•
A ^ G J - * " Cao su Buna
•
T i r Q - > C 4 la chat k h f , Q
C|« l o n g va
t r d I6n t d n tai d a n g r a n .
•
N h i e t d d n d n g chay va nhiet d o s d i t u o n g d d i tha'p, t i khd'i h o i n h d , t i n h t a n
t r o n g nirdc k e m .
•
C a c a n k e n t h i r d n g phfln c u e (|.i ^ 0 ) va fi,„ > \i„,„„ d o d d cac d d n g phan
trans
- an ken n d n g c h a y a nhiet d p c a o h o n n h u n g l a i s d i d nhiet d d tha'p h o n so
v d i cac d d n g phan cis t i r o n g I'rng.
CH4-*- D
E
C2H5OH
D — • E — • F — • HCHC
•
A n k e n hau nhir k h d n g tan t r o n g nude va la nhOng chat k h d n g m a u .
4. Tinh chat hoa hoc
L i e n ket n c i i a anken k e m ben At hi dut de tao thanh l i e n ket a v d i cac n g u y e n tir
+NaOH
khac nen dh t h a m g i a phan I'rng c d n g , phan i h i g t r u n g h o p va phan ting o x i hda.
+
Phsin umg cong
a) Cgni> //. —> ankan
C„H2„ + H ,
Nlian
Goi
—
> C„H2,n.2
xet : K h i g i a i toan ciin l u u y :
X la h d n h o p a n k e n va
ban d a u , Y la h d n h o p t h u d u p c sau p h a n iJng. T a
cd :
•
N e u m o t h i d r o e a b o n m a c h h d phan u'ng vira d u v d i
t h e o t i le m o l 1: 1 t h i
d d la a n k e n .
•
N e u 2 h a y n h i e u a n k e n c d n g v d i H2 v d i c u n g h i e u suat t h i ta c d the' thay h d n
h o p b a n g c d n g t h u c t u o i i g ducmg C - H
C-H
- + H .
nank.n p i f
= I n 2 Pif
C - H -
^,
= "umk - n,,„
r
'
Chi'i y: K h d n g the' d u n g each nay neu cac anken c d n g h o p v d i H , k h d n g c u n g
h i e u suat.
Sffcld chuSiphan li-ng hda hpc Httu ca- Nguyln XuQn Tru&ng
•
2CH,-Ci l - C H , + 2H,0 — f ^
CH3 - C H - CH3 + C H 3 - C H , - C H , O H
V i h6n hop X, Y c6 cung s6 mol C, H nSn d6't chay h6n hop A hay B d^u cho
OH
cung ke't qua :
d6'tX
'o'CO2
va
= n^
Ancol isopropylic
(spchinh)
d6'tY
r» sinh ra do d6't X = n^Q va nu r, sinh ra do dot Y
+ Phan iimg trung hop
'H,o
t", xt ->
Do do khi lam toan, neu gap h6n hop sau khi qua Ni/t° dem ddt (h6n hop Y ) thi
thay vl ti'nh toan vdi h6n hop Y (thucmg phufc tap hem X ) ta c6 t h i dung cac
- 1 < 1 (gia sCr
nCH, = (pH
MY
X, Y do o cung dieu kien t°, ap sua't)
h) Cdna halogen (CI..
p
Xt
[-CH, —CH-]„
CH,
polipropilen (PP)
cci.^
C„H,„X3
+ Phan iimg oxi hoa
! I''
a) Oxi hda hodn toan :
Phan ling lam mA't mau dung djch brom dirge dung d l nhan bi6't cac hop chait
C„H2„+
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
Quy tac Mac-c6p-nhi-c6p : K h i c6ng mot tac nhan bat d6'i H A (axit hoac
nucfc) vao liSn ket d6i (C = C) ciia anken thi san p h i m chinh dugc tao thanh
dang thu duoc :
"CO2 = " H 2 0 hoac n^o^ = 1-5 n^^^Q ^
MI
CH,
•
CH = CH2
t
+ H"
I
cr
lankan
• C H , - C H 2 - C H 2 C I (spphu)
Giai thich quy tac : Do g6'c ankyl day electron lam cho lidn ket 71 bj phan cue,
n6n ion duong dd gdn vao cacbon mang didn am va ngugc lai.
Kha nang phan ling c6ng : H I > HBr > HCl > H F
•
C6ng H , 0 - > ancol
C H , = C H , + H3O
'-^—^ CH.CH^OH
t"
'
Ancbletylic
=
"H2O '
nc02
• D o t chay h6n hop anken + a n k i n (ankadien) t h i n^.^^ > n^^^Q va
(spchinh)
CI
•
*
• D6't chay h6n hop ankan + anken ( x i c l o a n k a n ) t h i n^^Q^ > n^^o
(cacbon c6 bac tha'p hon) va phdn mang didn am ciia tac nhan (X~) gSn v^o
r*CH,-CH-CH3
Cac hidrocacbon do thu6c day d6ng
dang anken hay xicloankan
do phAn duong ciia tac nhan (H*) gin vao C ciia n6'i d6i mang di6n am
cacbon ciia n6'i d6i mang dien duong (cacbon c6 bac cao hon). V i du :
"^^'"^
• K h i d6't chay mot hidrocacbon hay nhidu hidrocacbon thu6c cung day d6ng
c) Cons HA (A = halogen, O H " , OSO,H")
•
^
Nhan xet :
dang tac dung voi brom theo t i le mol 1: 1 thi cac hidrocacbon do la anken.
•
polietilen (PE)
t",
CH,
Nhan xet :
•
I-CH.-CH.-,.
Br,)
C„H,„ + X , (dd)
- C - ]„
"CH, = CH,
12
Mx < M Y ^ d (XA') = = A = ^ =
m^ = mv va nv < nX
[-c
Vidu:
phan ling dot chay X de ti'nh nco ^ va UH ^ o•
Ancol propylic
(spphu) ,^
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.
3C„H3„ + 2KMn04 + 4 H , 0
3C„H2n(OH)2 + 2 M n 0 2 l + 2 K O H
Vi du :
3CH.=CH2 + 2KMn04 + 4 H , 0 ^
3CH2-CH2 +
OH
(mau tim)
MnO^J-+ 2 K O H
OH
17
Nhdri
xet:
D i r a v a o sir b i e i i d o i m a u c u a d u n g
d i c h ( d u n g d i c h m a u ti'm ->
bi
nhat mau va c6 ke't tiia mau den xuS't hifen) phan ung nay duoc dung de nhan r a
sir CO mat cua n6'i d6i, nO'i ba.
+
Dung djch K M n 0 4 dam dac, o t° cao oxi hoa manh lam dut mach cacbon tai
II, ANKADIEN
1, C o n g thufc C h u n g :
n6'i d6i cho xeton, axit cacboxylic hay C O , tuy theo CTCT cua anken. Phan
c a n c l i vao vi trf ciia hai lien ke't d6i ma ngucri ta chia lam 3 loai :
ling nay dugc dung de' xac dinh vj tri cua n6'i d6i dua vao ca'u tao cua san
•
Lien ke't d6i lien : Hai lien ke't d6i of l i ^ n nhau. V i du:
C H , = C = CH2
Trong cong nghiep ngirofi ta oxi hoa nhe etilen de san xua't C H 3 C H O
2CH2 = C H 3 + 0 ,
+
•
^^cx,,c.cx,
t°
^
•
2CH3CHO
Phan ling the
6 nhiet d6 tha'p cac anken d l tham gia phan ling c6ng clo, nhimg b nhiet d6
Lien kd't doi lien hgp: Hai lien ke't d6i b each nhau m6t lien ke't don. V i du :
CH2=CH-CH=CH2
CH2=C(CH3)-CH=CH2
buta-1,3-dien (butadien)
2- metylbuta - 1,3 - dien (isopren)
Vfdu:
CH,Cl-CH(OH)-CH2Cl + HCl
C,.H,„,,
^ k i : ^ c „ H 3 „ + H,
p
+
Dehidrat
huu CO.
+
Phcin ifng
•
Cong
> C„H,„ + H , 0
Cdn}> H2 vao ankin (xt: Pd) hoar ankadien
H3
—
^
^
(xt: Ni) tuang
ifng
C„H3„
•
+
khoi dan xiidt monohalogen
C„H2„, ,X
+
'^Q";""-"'
— ^
Ni
->
CH3-CH-CH2-CH3
CH,
Cong halogen
(X2) vd hidrohalogenua
(HX)
ra san ph^m cong -1,2, nhiet d6 cao Uu tien tao ra san ph^m c6ng -1,4.
CH3-CH,-CH=CH,
cua ankan tUcfng ifng
> C„H2„ + H X
Loai X2 ra khoi dan xudt a, P - dihalogen
R - C H X - C H X - R + Zn
18
^
+2H2
-> C H 3 - C H 2 - C H 2 - C H 3
tao ra h6n hgp cac san phslm c6ng- 1,2 va -1,4. 6 nhiet d6 tha'p uu tien tao ra
ankan
Loai HXra
Ni
Butadien cung nhu isopren c6 t h ^ tham gia phan ling cong X2, H X va thucmg
CH,=CH,
C H 2 = C H - C H = C H , + H, —
Crackinh
hidro
CH3
t"
+
cong
CH2 = C - C H = CH2
t°
Vi du: C H H C H +
hoc
CH,=CH-CH=CH, + 2H,
t^no'c
C„H,„_, +
Isopren hay 2- metylbuta-1,3- dien la cha't long, kh6ng mau, s6i b 34°C
Deu la nhQng chat khdng tan trong nu6c nhirng tan dugc trong cac dung moi
hoa ancol ti/cmg ifng
C„H3„„OH
+
Butadien hay divinyl la chat khong mau, c6 mui dac trung, t° = - 4''C
h) Tinh chat hoa
ankan tUcfn^ i?ng
Dehidro
-
C H 2 0 H - C H ( O H ) - C H , O H + 2NaCl
CH2C1-CH(0H)-CH,C1 + 2NaOH ^
5. Dieu che
+
-
A l y l clorua dugc diing de d i l u che glixerol
+ H,0 ^
3, Butadien v a isopren
a) Tinh chat vat li
A l y l clorua
CH2=CH-CH2C! + a,
'
,
2
3
4
5
CH2 = C H - CH2 - C H = CH2 penta - 1,4 - dien
ling the' boi d o . V i du :
C H , = C H - C H 3 + C K — 5 5 2 1 ^ C H 3 = C H - C H 3 C 1 + HCl
propadien (anlen)
Lien ke't doi khong lien hgp: Hai lien ke't d6i each nhau nhieu lien ke't don.
•
cao (500 — 600°C) m6t s6' anken dSu day d6ng d i n g c6 t h ^ tham gia phan
•
S3)
(n
C„lii„-i
2, P h a n loai
ph^m oxi hoa.
•
(DIOLEFIN)
cua ankan tuctng ifng
R-CH=CH-R + ZnX,
+
Phan i/ng trung hcq?
•
Trung hgp — 1,4 d^ cho polime c6 tinh dan h6i cao (cao su)
nCH,=CH-CH=CH2
—^'^"'"^
n C H 2 = C - C H = CH2
CH,
p, t°, xt
)
[—CH2-CH=CH-CH2—]„
polibutadien (cao su buna)
-CH2-C = CH-CH2|CH3
poliisopren (cao su isopren)
19
p, t ° . Xt
n CH2 = C - C H = CH2
-CH2-C = CH-CH2
I
CI
tir c a c b o n (^^^^ = c = 3,29) d o d o cac a n k - 1 - i n c6 H l i n h d6ng, d ^ b i d u t d ^
clopren
d o n g v a i t r o tac nhftn t r o n g phan l i n g c6ng hoSc phan l i n g t h e ' v d i k i m l o a i .
p o l i c l o p r e n ( c a o su c l o r e n )
L i e n ke't ba ( C = C ) b a o g6m 1 l i e n ket a va 2 l i e n ket TT k e m b ^ n . T u y n h i e n
M o t phSn CO the t r u n g hcrp - 1 , 2 d^' t a o t h a n h p o l i m e k h 6 n g d a n h 6 i . D i e u nay
•
iii>'' g i a i t h i c h t f n h d a n h o i k e m cm m 6 t s6' l o a i c a o su t 6 n g h a p .
p. t°, xt
nCH,=CH-CH=CH,
lien ket 71 t r o n g l i e n ket ba hcri b^n h o n lien ke't 71 t r o n g l i e n ke't d o i nen phan
,
iJng c6ng v a o l i e n k e t ba x a y ra k h o hem phan l i n g c6ng v a o l i e n ke't d6i.
-CH2-CH-
3. T i n h c h a t v a t l i
• ('1 nhiet d6 thircmg :
CH = CH.
^
n = 2 ^ 4 la chaft k h i
5. D i e u c h e a n k a d i e n
n > 17 l a chat ran
a) D e h i d r o h o a b u t a n hoSc buten a n h i ^ t d 6 c a o (GOO^C) c 6 m a t cha't x u c tac
(Cr,03):
CH.CH^CH^CH, — ^ " • P - " ^
'"'P'"^
4. T i n h c h a t h o a h o c
Phan l i n g x a y ra q u a 2 g i a i doan ( g i a i doan 1 t a o san p h ^ m d a n g cis)
, 4_— >.
Anken
—>
xt.t
'
'
Ankan
xt,t
M u 6 ' n d i r n g phan l i n g 6 g i a i doan t h i i nha't ( a n k e n ) n g o a i t i Id m o l 1: 1 c ^
_^ci/NH.ci
'•i^i—> C H , = C H - C = C H — ^ - ^ - ^
chu y d u n g cha't x i i c tac t h i c h h o p .
CH,=CH-CH=CH,
Pd,
C H s C H + HV
d ) T 6 n g hcrp K o n b e ( D u e ) :
CH^CH + 2H.
2 C H , = C H - C O O N a + 2 H . O — i ^ ! ^ C H , = C H - C H = C H , + 2C0,T
+ 2 N a O H + H,T
cheisopren
Ni, t°
*
CH,=CH,!
CHj-CHj^
Nhan xet : N e u g o i X l a h 6 n h o p a n k i n v a H , ban d d u , Y l a h 6 n h o p t h u duoc
sau phan l i n g . T a c 6
•
nH.pu
=nx
-nY^a,„^i„pu
D e h i d r o h 6 a isopentan v a isopenten (san p h ^ m c r a c k i n h din m o ) ^
H a m l u g n g C, H t r o n g h a i h 6 n h o p X v a Y l a n h u nhau nen k h i g i a i toan d ^
CH3-CH-CH2-CH3
d o n g i a n ta thay d6't chay h 6 n h o p Y bang dd't chay h 6 n h o p X .
'"•"•"^
) C H 2 = C - C H = CH2 + 2 H 2
CH3
CH3-C = CH-CH3
CH3
^"•'^•"^
)
1. C o n g thurc C h u n g : C „ H 2 „ . 2
mx
v a ny < nx - > Mv < My
d (X/Y)(=
= r -
= _ L = _ L < 1 (g,a
"X
su X , Y d o 0 Cling d i e u k i e n ap sua't, nhiet d o )
CgnsX2(X=CI,
•
(n>2)
^
Br)
Phan l i n g x a y ra q u a h a i g i a i doan (giai doan 1 c 6 n g trans). M u d ' n d t o g phan
ting a g i a i doan t h i i nha't t h i cSn thuc h i e n a nhiet d 6 tha'p.
2. C a u t a o
•
= mv
MY
CH2=C-CH-CH2 + H,
III. ANKIN
Q . H : , , —2
'
^ QiH2„_2X2
^
> C„H2n_2X4
T r o n g p h a n tijf c 6 l i e n ke't b a ( C = C ) vdri n g u y a n tir C l a i h o a sp n e n phan t i r
Nhan xet:
CO ca'u t a o t h a n g , g o c h o a t r i 180°.
• N o i c h u n g a n k i n l a m ma't m a u nu6c b r o m c h a m h o n a n k e n .
0
•
fH
Ankin
^ CH,=CH-CH=CH, + H ,+ 2H.O
400-50(1" C
+ Dieu
1^^,,
Phan ihi}> coni>
c ) D i tilf a x e t i l e n
2CH^CH
I
a) Cgn^ hicfro:
) CH:-CH-CH=CH, + H,
MgOiA\,o,
Cac a n k i n ra't ft tan t r o n g nude, tan duoc t r o n g m o t so d u n g m d i h i h i c o .
+
> C H 2 = C H - C H = C H , + 2H3
b) D e h i d r o h o a va h i d r a t hoa ancol e t y l i c n h d x u c tac ( Z n O hoac M g O v a AUO,)
2CH,CH,OH
'
n = 5 - > 16 l a chat l o n g
+ Dieu clie'hiita - 1J - dien
C4H8
''^
D 6 d a i l i d n ke't b a ra't ngdn ( 1 , 1 9 A ) nSn electron 6 gSn n h a n va b i nhan hut
m a n h n e n n g u y e n tir C a n6'i ba c 6 d o a m diSn I o n nha't t r o n g cac l o a i n g u y d n
•
K h d i lucmg c i i a b i n h d u n g d u n g d i c h b r o m tang l e n l a k h d i l u c n g ciia a n k i n
ha'p t h u .
,,
C6ngHX(X^a,Br.I)
•
Phan l i n g x a y ra q u a h a i g i a i doan v a g i a i doan sau k h o h o n g i a i doan t n r ^ .
Cty TNHH MTVDVVHKhang
Sff dd chuSi phan irng hda hpc Hihi cff - Nguyen Xuitn Trir&ng
CH.CH + HCl
) CH3=CHCI
— ^
Cac phuang trinh hoa hoc :
CH = CH + 2AgNO, + 2NH3 -> AgC = C A g i + 2NH4NO3
-CH2 - C H -
Cl
CH, = CHCl + HCl
•
R-C = CH + AgNO, + NH3
CH = CH + 2CuCl + 2NH3 -> CuC = CCui + 2NH4CI
> CH3-CCI2-CH3
D6ng (I) axetilenua (mau do)
R - C = CH + CuCl + NHj -> R-C = CCui
CI
cl) Con^ mfdc (hidrat
hoa)
Axetilen + H2O
•
•
) [CH2=CHOH] ->• CH,CHO
(kh6ngb^n)
Xeton
R,-C=C-R, + H O H '
,,»,^„., ,
R, - C H = C - R 2
-
.
.
i
•
R.-CH.-COR,
axit
Vi du:
•
qua blnh dung dung dich AgNO,/NH, thu duac hdn hap Y. Ta c6
" a n k - 1 - in =
Iflbinh ling
CH,COOCH = CH,
xt,f
-CH2 - C H COOCH3
vinyl axetat
Phan
AgC = CAg + 2 H a -> CH = CH T + 2 A g C l i
H6n hap khi X (hidrocabon no, hidrocacbon khdng no, khi khac) di cham
axetic
C H ^ C H + CH,COOH ^
+
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)
(khdng bin)
Nhan xet Neu mot hidrocacbon tac dung v6i nude tao ra andehit axetic thi
hidrocacbon do la axetilen.
Cong
Trong day d6ng dang ankin chi c6 axetilen phan utig vdri cdc ion kim loai
theo ti le mol 1: 2 con cac ank -1 - in khac phan ling theo ti IS mol 1 : 1 .
• Co the dijng cac phan vrng trfin di nhan bife't axetilen va cac ank - 1- in.
A . I .
OH
e)
<^
Nhgn xet ;
Andehit axetic
Cac d6ng dang + HjO
+ NH4CI
(mau do)
CH=CH + H , 0
•
R - C = C A g i + NH4NO3
(mau vang nhat)
Phan ung c6ng vao d6ng dang axetilen tuftn theo quy tac Mac-cop-nhi-cop.
CH3 - C = CH2
»
Bac axetilenua (mau vang nhat)
Vinyl clorua
Poli(vinyl clorua)
CH, - CHCl, ( 1 , 1 — dicloetan)
CHj-C^CH + HCl
Vift
Khac vdi anken, ankin kh6ng triing hop thanh polime. Hai phan tij axetilen c6
th^ c6ng hop vori nhau de' tao thanh vinyl axetilen.
"
> Hy)
(nx
= ^ a n k - 1 - in
T l k f t lua — Tlmufli ank - I - In
+
Phan
I'/ng oxi hoa
a)
Oxi hoa hoan
toan (phan
I'mg (hay)
C„H,„ _ , +
poli(vinyl axetat) (PVA)
I'rng dime hoa vii trinie hoa
Hx
Nhan
•
nCO, + (n — 1 )H30
O:
xet :
Neu bai toan cho dot chay mdt hay mdt sd hidrocacbon mach hd, thudc cung
day ddng dang thu duac :
2CH = CH
""'f
> CH. = CH - C = CH
"cOj ^ " H J O
'^^^^
" O j *^^'^"co2~^
hidrocacbon dd thudc day
vinyl axetilen
ddng dang ankin hay ankadien va
Ba phan tir axetilen c6 the cong hap vdi nhau d6 tao thanh benzen.
3CH = CH
+
Phan
^ ^ ^ ^ C,H,
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 djch AgNO,/NHi cho ke't tiia mau vang, tac dung vdi dung djch
CuCl/NH, cho ket tiia mau do.
"hh =
•
nH20-"co2
^^^^ " h h =
2(l,5nco2-^o^)
Dd't chay hdn hap ankan + ankin (ankadien) hoac anken + ankin (ankadien)
+ anken
-
Ne'u nco2 =
-
Neu nco^
-
Ne'U
"H2O
nco2>"H20
^
"-'kin
".mkn,
=
<
"anki" >
"ankan
n,„k,„
"ankan
H
/
Sadd chuSiphdn
li-ng htia hpc HOu ca - Nguyin Xudn Trir&ng
Di tirddn xudt ch,'ra Ag cua ankin va ddn xudt chira halogen cua ankan
D6't chay h6n hap anken + ankin (ankadien) thi
> n H , 0 va n.
•
= nCO- - n
Phircmg phap tang mach cacbon.
AgC=C-R+R'Cl -> R'-C=C-R + A g C l i
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 + 2KOH + 2 H 2 O
^
C 2 H 2 + 2KMn04 + 3 H 2 S O 4 ^ 2C02t + 2MnS04 + K,S04 + 4 H 2 O
SCHj-C^CH + 8KMn04 + 12H,S04 -)•
,
Phan ling tuong tir doi v6i dSn x u ^ chufa Cu ciia ankin.
B. BAI TAP C H u 6 l PHAN UNG
Bai 1.
(NaOOC)2CH=CH
+ SCO,! + 8MnO, + 4K,S04 + I 2 H 2 O
Nhan xet : Co th^ diing phan ung lam mat mau dung dich thu6'c tim di nhan
biet cac ankin. So vdi anken thi t6c d6 phan utig didn ra cham hon.
5. Dieu che
5CH3COOH
+
C2H5OH
C2H4Br2,
n
C2H,C1
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,0
h) Tic than da, da v6i -> CaC, (dat den)
500° C
Than da
CaCOj
Hiro'ng dan giai
-> than c6'c (C)
-
CaO + 3C
QH|o
CH
1. NaOOC-CH=CH-COONa + 2 N a O H
) C a O + CO,T
2.
2000° c
16 di^n
CaC + CO
'"''^
4.
Nhan xet : 6 nhOng nod c6ng nghidp din khi chua phat trien nguofi ta thuong
di^u che Q H , theo phuong phap trdn.
2C + H ,
) CH,
di$n
'
Dieu chedong dang cua axetilen
^
'
> C,iH2„ _ 2 + 2 H 2
h) Di ti( dan xudt di halogen
H X
I I
R, - C - C - R , + 2KOH
X
H
+ 2KMn04 +
2H2O
C2H4(OH)2 + 2Mn02 + 2KOH
;
'^^"''"'^ ) C 2 H , + C 2 H 4
Ni.l"
-> C 2 H ,
->C2H4 + H2;
9. C H 4 + H2O .
, C2H3OH
10. C H , O H - ^ i ^ ^ C 2 H 4 + H2O
-
mrc
11. C2H5CI + NaOH
12.
an col
-> R , - C s C - R 2 + 2KX + 2H,0
;
'""^""'^ > C2H4(OH)2
loang, I
a) Dehidio hoa ankan ti/crng I'/ng
I I
C2H4
7. C H . + H , '
8. CjHe -
+ 2Na2C03
+ ZnBr2
nCH2=CH2-> [-CH2-CH2-],,
6. C 4 H , o
AgC = CAg + 2HC1 -> C H = C H T + 2AgCl^
CuC = CCu + 2HCl ^ C H s C H T + 2CuCli
Q,H2„ + 2
C2H4
'
d) Tii muoi axetilenua
+
C2H4
+ [O] + H 2 O
Hoac vidt:
5.
"^""^"""^
C3H4
^
B r 2 - > C2H4Br2
3. C2H4Br2 + Zn ^
CaC, + 2H,0 ^ Ca(OH), + C H ^ t
c) TCr C va H2:
C2H4 +
—
{
Q H , O H + HCl
1 3 . C H , + Cl2
— ^
C2H5CI
C2H.,0H + N a Q
+ H2O
->C2H,C1 +HC1
cry TNHHMTVDVVHKhang
Sffdb chudipItdn li-ng luiu lt(>c HCru cff ~ Nguyin Xu&n Trir&ng
2. CH3 - C H - C H , + NaOH
Bai2.
1. Ancol butylic ^ Butilen ^
Butan ^
8
Br
MetanAxetilen
7
6
OH
3. nCH,-CH=CH, -> f - C H - C H 2
C H ^ ^ C H 4 ^ CH,C\ C4H10
CHjCOONa
QH, \,
Br
Propanol - 2
. CH3-CH-CH2
Br
3
4
4. CH,-CH=CH: + B r 2 - > C H 3 - C H - C H 2
QH4(OH),
3. C3H6 \ - brompropan
(C,H,)„
^
CH3
Etilen « - Brometilen <- Etilenglicol <— Etilen
2.
C H , - C H - C H , + NaBr
Br
+ 2NaOH|„5„g — ^
Br
Bai3.
5
1,2- dibrompropan
Propilen glicol
CH,OH^^4
Hiro'ng dan giai
O 1. CH,-CH,-CH,-CH.OH
HO-CH3-CH,-COONa
Cao su buna
iK(rc
2. CH3-CH,-CH,=CH, + H ,
3. C4H,o
^^"'-•'^'"^ > C H 4 + C,H,
,. '^"f^,
Vinylaxetilen <—
, ) C,H. + 3H.
lam lann nnann
5. C H . + H .
C,H,o
C^H,
Hirong dan giai
" "
1. HO-CHo-CH.-COONa + NaOH — ! ^ CHi-CH.-OH + Na.COj
)CH4
"^'^'^""4
6. QH4 + [ 0 ] + H30
)CH4(OH)3
2. 2QH,OH ^ ^ i ^ C H , = C H - C H = C H , + 2H30 + H ,
7. C2H4(OH)2 + HBr -> QH4Br + IH.O
8. C,H4Br3 + Zn -> C3H4 + ZnBr,
3. CH,=CH-CH=CH, + Br,
© 1. 2CH,COONa + 2H,0 _ J ! E ^ C 2 H , + 2CO. + 2NaOH + H^.T
2. CH6 — ^ C H 4 - i -
Br
C,H,C1
5. CH,C1 + 2 Na + C\-C.H,
6. C4H,o
©
-> C4H,o + 2NaCl
^"^'^'"'^ > CH4 + C,H,
7. C,H, + [O] + H.O
- ^ C H , - C H - C H = CH2
I " I
Br
Br
^CH2-CH=CH-CH2
H,
3. C3H4 + 2KMn04 + 2H,0 ^ C3H4(OH)2 + 2MnO, + 2KOH
4. a H 4 + HCI ^
^
> C4H.Br4
CH,=CH-CH=CH,
> CH,-CH,-CH,=CH, + H , 0
4. 2CH4
C H 3 - C H - C H 2 + 2NaBr
I
OH
OH
"^^""-^ ) C,H,(OH)3
1. CH.,-CH=CH2 + HBr -> CH3 - C H - CH3
Br
4. CH,=CH-CH=CH, + Br, ->• C H , - C H - C H - C H2
" " 1 ^ 1
I
I
Br
Br
Br Br
5. nCH2=CH-CH=CH:
[-CH2-CH=CH-CH2-]„
6. CH2=CH-C=CH + H2
CH2=CH-CH=CH2
7. 2CH=CH
) CH,=CH-OCH
Br
Vi?l
Sar ad chuSi ph6n lirng hda hpc HOu ctr - Nguyin XuSn Tru&ng
2) C H , = C - C H ^ C H 2
Bai 4.
1.
'l' > f-CH2-C = CH-CH2-'
CH3
CH,
Glucoza
2
3
*• Rirooi etylic — ^ B u t a d i e n - 1,3
4 ^ Cao su buna
<^
^
t'
Tinh bot
CH2=CH-COONa
Plivinyl etilen
> CH2=CH-CH-CH2
CI
-CH2-C = CH-CH2-
3)
-CH
-
CH-
4) C,H,2
CH.Br CH,Br
CH,
""-^'"^ )
5) n C H , - C H = C H ,
Q H , + C,H,
^-CH-CH2-^
CI
3.
C3H, - U C , H , - ^ ( C ^ H , ) ^
-CH2 - C - C H j
-CH2-C-CH2-CH2-
CH,
Cho 3 san ph^m
C4H6Br2
+ nHCl
CH,
Bai 5.
CH3
dpdd ^
H,
<
!
(COONa),
Hiring dan giai
O 1) (QHioOj),, + n H , 0
2) Q H , , 0 ,
C H , = C H - C=CH
nQH,A
> 2 C , H , 0 H + 2CO,
3) 2 Q H 5 O H
^'2"3 ) C H , = C H - C H = C H , + 2H2O+ H^t
CH3CHO
C.H,
450" c
,0p
4)nCH, =CH
I
-CH, - C H -
XI
I
CH=CH,
Ag - C s C - A g
CH = C H .
CH, - CHCl,
(COOH),
1) 2 C H , = C H - C O O N a + 2 H , 0 — C H , = C H - C H = C H , + 2NaOH + 2 C 0 , t
H i r a n g dan giai
0
->CH2 - CH - CH = CH2
2) C H 2 = C H - C H = C H 2 + Br,
Br
Br
CH2 - CH = CH - CH2
Br
Br -
® I) C H 3 - C H - C H 2 - C H 3
CH3
Br
CH,
I
3) Q H ,
2H,
+ 2NaOH
-^""""^ > C : H ,
cn^h-^^^^'
C,H, + H ,
5) C , H , O H
Br
CH2 = C - C H = CH2 +
2) 2C + H ,
4)
3) C H , = C H - C H = C H , + Br, - > C H , - C H - C H - C H .
Br
O
1) N a - O - C - C - O - N a
Theo ty le 1 :2
Br
1
,
CH,=CH-C=CH
>C,H,
'If^;.
> C,H4 + H , 0
6) C H , C H O + H : - ^ C , H , O H
J C,H, + H , 0
"g„„,
^'^CHjCHO
> H , + 2Na,C03
8 ) C,H, + 4 [ 0 ]
Hoac vilt:
3C,H, + 8KMnO, + 4HjO
9) CH,-CHCl3
^
+ nNaOH-> nCHjCOGNa +
f-CH-CH,
'""^'^""^ > HOOC —COOH
3(COOH), +
CH = CH + 2HC1
e
10) CH = CH + 2HC1-> CH, - CHCl,
1) CaCO,
^ CaO + CO.
2000"f
^ CaC, + CO
900" r
11) AgC ^ CAg + 2HCI -> CH = CH + 2AgCli
2) CaO + 3 C
12)CH = CH + A g , 0
3) CaQ + 2H2O - > C2H2 + Ca(OH)2
Hay CO the vid't
-> AgC = CAg + H , 0
Hoac Viet: CH = CH + 2f AgCNHO^J^OH"
AgC = CAg + 4NH3 + 2H2O
CaC, + 2H" -> C2H2 + Ca-*
13) 2C2H,
4) C2H2
14) 2CH4
lilm lanh nhanh
LI
>
C.H2
i
+
l O
3H2
Bai 6.
— V i n y l axetat — ^
2. Da v6i — ^
— ^
Divinyl — ^
CaC.
Buten — ^
C.H.
4. C.H..
Hidro — ^
I
Etilen — ^
Vinyl axetilen
Butan — P r o p e n .
3. Dibrom etilen —!—> Axetilen — ^
— ^
Andehit axetic — A x i t axetic
Polivinyl axetat — ^ Polivinylancol
Voi s6'ng
e
Etilen glycol — ^
A
^' >
1) C2H4Br2 + 2KOHd
Axit oxalic.
'''"^^""^ ) HOOC-COOH
4) NaOOC-COONa + 2NaOH -> H . + 2Na2C03
Pd
I
CH3-C-CH3
— UB
E ^
O
2) CH^CH + H , 0
) CH3CHO
OU—OU
(
•
OCOCH 3
30
'''"'^""^ > HOOC-COOH + 2H2O
-CH-CH2-
^0CbCH3
-CH-CHo
3) C H 3 C O O H = CH, + NaOH
5) n C H ^ C H
^2lo"r
Ca
280"(•
CHjCOONa + C H 3 C H O
>CH3CHO
[-CH=CH-1
Hay (CH)2„
©
1) CH3-C=CH + H 2 O ^
CH3 - C - C H 2
OH
OH
4) C H 3 C O O H + CH=CH -> CH3COOCH=CH2
-CH-CH2 -
HO-CH.-CH,-OH
2) nCH3-COOCH=CH2
3) CH,CHO+ ^ O . - ^ ^ ^ C H . C O O H
5) nCH3COOCH=CH,
^
CH3-COOCH=H2
4) C2H2 + H2O
C,H, t + 2ZnBr2
dd KMnO.
1) C2H2 + C H 3 C O O H — ^
O
OH
I) C2H4Br4 + 2Zn
> CH2=CH2
7 ) HO-CH2-CH2-OH + 4[0]
Hirong dan giai
O
) C2H2 + 2KBr + 2H2O
6) CH2=CH2 + [O] + H .
CH3-C-CH3
C4H10
> CH4 + C 3 H ,
5) H2 + C2H2
OH
-> C,H.
7) CH3-CH2-CH=CH2 + H .
-> CH3-CH,-CH=CH,
3) HOOC-COOH + 2NaOH ^ (COONa). + 2H2O
CH,CHO
5. C H . - C ^ C H - ^ C H 3 - C - C H 2
> CH,=CH-CH=CH,
6) CH2=CH-CH=CH2 + H2
2) C2H2 + 4 [ 0 ]
Axit oxalic — ^ Oxalat natri
OH
6. RBr,
Pd
Ni
8) C4H,o
^ CH,COOCH=CH2 — -> P.V.A
Cupren
) CH2=CH-C=CH
5) CH2=CH-C=CH + H2
1. Tetrabrom axetilen — A x e t i l e n — ^
I
OH
OCOCH3
8Mn02 + 8 K O H
CH-CH2-
2) C H 3 - C - C H 2
OH
+H2O
I
CH3-C-CH3
OH
OH
Hudng dan giai
I
3)CH3-C-CH3
-> C H 3 - C - C H 3
OH
+ H.O
,- '.^'"u"': . >CH = CH + 3 H ,
lam lanh nhanh
O
1) CH.Br. + 2KOH
2) 3 Q H ,
> QH,
(1) 2CH,
^
.0
> Q H ^ t + 2KBr + 2H,0
(2) 2 C H = C H — ^ ^ ^ ^ C H = C - C H = CH2
(3) CH = C - C H = C H 2 + H 2
>CH,^CH-CH=:CH.
Pd/PdC03
3) QHft + QH4 ^ Q H , - C H , - C H 3
4) Q H , - C H . - C H ,
5) Q H , - C H = CH, -
6) Q H , + H:
> QH,-CH=CH, + H ,
-CH-CHj-^
(4) CH2 = C H - C H ^ C H 2 + 2 H 2
(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: C H : ; B: Q H , ; C: C,H^- D: C H , ; E: C H 4
CH,=CH:
Bal 7. Hoan thanh so do phan urng sau :
606
(I)
(1)
(3)
-C2H2
CH,
C2H6
C4H
4"4
C2H4
Hirong dan giai
(1) 2CH,
(2)
I5()()"c
-»-CH
lam lanh nhanh
3CH^CH
(3) 2 C H ^ C H
(4) CH = CH + H ,
^
2CH,
,,
I5i«)"c
, , , , >CH s C H + 3 H ,
lam lanh nhanh
(2> 2CH = CH-
11.1
^CH3 - C H - C H 2 - C H 3
>CH3-CH3+CH2^CH;,
^lA
= CH + 3 H ,
(5) C H 3 - C H 3
) C H ^ C H + 2H2
) C H ^ C - C H = CH,
^CH2
'"^"''"^ >CH2^CH2
(6) C H ^ C H + H ,
(7)
CH3-CH3
XI.I
-j-CHj =CH2 +H2
(8)
CH2=CH2+H2
^CH3-CH3
=CH2
(5) C H s C H + 2 H 2 - ^ J p ^ C H 3 - C H 3
Bal 10. Viet phiromg trinh hoa hoc ctia cac phan li^ng trong chu6i bie'n hoa sau (bie't
A, B, C, D, E la cac hidrocacbon):
Bai 8. Hoan thanh so do phan irng sau :
C3H8
(1)
(8)
C4H4
A:
32
->CHsC-CH-CH,
(4) C H 3 - C H 2 - C H 2 - C H 3
6"6
CH4
^
(3) C H = C - C H = C H . + 3 H -
)CH
Pd/PdCO
>CH3-CH2-CH;-CH3
CH4;
Hirong dan giai
B: C,H,: C ' .H,o; D: QH^; E: C H 4
33
(1) C H , - C H ^ - C H ^ - C H ^
•
""
>CH^+CH3-CH
=CH^
(7)
CH2=CH2+H2
>CH3-CH3
(2)
CH^-CH=CH2+H2-^^^^CH3-CH2-CH3
(8)
CH3-CH3
(3)
CH.-CH.-CH,
(9)
CH= CH + | 0 2 - ^ ^ 2 C 0 2 + H 2 0
(4)
CH3-CH2-CH2 -CH3
(10)
C4H4+5O2—^4C02+2H20
(5)
CH3-CH3
(6)
CH^CH + H,
>CH^+CH^=CH^
) C H 3 - C H 3 + C H 2 =CH2
" " " > C H ^ C H + 2H3
^'^"''^'^"^
> C H ^ C H + 2H2
(11)
c,H,+y02-^4C02+3H20
(12)
C4H,„+y02-^4C02+5H20
(13)
C2H4+4O2—^2C02+2H20
(14)
C2H^+-^02^%2C02+3H20
)CH2^CH2
(7)
CH3-CH3^^^^CH2-CH2
(5)
CH3=CH2+H2
+ H2
>CH3-CH3
Bai 11. Viet phirong trinh hoa hoc cua cac phan irng trong chu6i bien hoa sau (bifi't
A , B, C, D, E, F, G la cac hidrocacbon) :
Bai 12. Hoan thanh chu6i bid'n doi sau :
(4)
PE
(5)
Propan - >
AUCs-^ A - ^ B
X ^-^ etyl hidrosunfat
|(4)
(2)
C 0 2 ^ E
etylen oxit
Huo'ng dan giai
G-^
X la CH,=CH3
F
(7)
Hirong dan giai
A : CH4; B: C,H,; C: QH4; D: C4H,; E. QH,o; F: C H 4 ; G: C H ^
(1)
Al^C3 + i 2 H 2 0
(2)
2CH,
^
>3CH^+4A1(0H)3
,
> C H ^ C H + 3H2
l a m lanli nhanli
2
'f'"'"^;
(3)
2 C H = C H - ^ ^ ^ C H ^ C - C H = CH2
(4)
C H ^ C - C H ^ C H , ' ' ^ ' ^ ' ' ^ ' ^ " 3 >CH2 = C H - C H = C H 2
J
(5) CH2 - C H - C H = C H , + 2H2
(6)
CH3 - C H , - C H 2 - C H 3
(1) C H , = C H ,
) (-CH3-CH.-)„
) CH4 + CH,=CH3
(2) QHg
(3) CH,=CH2 + H O S O , H
(4) C H , = C H , +
-
> CHj-CH.OSO.H
)
CH2-CH2
-
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)
)CH3 - C H j - CH2 - CH3
>CH3 - C H 3 + C H 2 = C H 2
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.
34
35
Cty TnrHHUTTVTfvmiinang
Hirdnng dan giai
(X) (hidrcKacbon) -> (Y) -> etyl clorua
X c6 the' la C2H2 hoac C4H,o
- Ne'u X la Q H , thl Y la C,H4 hoSc QH^
- Ne'u X la C4H,o thl Y \h C.H^
V i du:
X la C4H10 thl Y la
C4H 10
Crackinf!
5 2CH,
'
l(X)"C
' " ' ^ ' ' ^ > CH,=CH-CH=CH,
7. nCH2=CH-CH=CH2 — ^
^ CH,=CH, + C H , - C H ,
CH3-CH3 + a,
c»cig.NH4Ci ^ c H , = C H - O C H
•
6. C H , = C H - C ^ H -K H,
QHj
^ H ^ - C H = CH-CH2>„
V J?0
-» C H 3 — C H , — C H , - < : H ,
8. CH,=CH—CH=CH, + 2H2
) CH3CH2C1 + H Q
rip
"*
t"c
Bai 17. Hoan thanh chu6i phan umg sau :
B^i 15. Hoan thanh chudi bie'n d6i sau:
(A,B. D chi chura 2 nguyen t6 C va H )
(A)
(2)
Axetilen
(1)
etan
C,H
•2"6
C4H4
(5)'
(3)
A2H2 ^
C H 4 ^
(6)
C2H4
JII^
PE
,,(8)
\B)_(5)^ (D)'
C2H4(OH)2
Hirong dan giai
Hv&ng dan giai
(1) HC=CH + 2H,
) QH^
(2) H C ^ C H +
, c.H,
> CH,=CH,
> CH4 +C,H4
2, 2CH4
(3) CH,=CH.+ H.
(4) 2C,H,
) CH3=CH-C^H
13 2C,H,
Q H , + 3H,
"^"^'Z'^"^"^' > CH,=CH-C=CH
1()()"C
(5) CH,=CH-C=CH + 3 H ,
"'""^
> CHj-CH^-CH^-CHj
Pil/HfiCO,
4. CM,
(6) C H j - C H . - C H . - C H ,
''"''""^ > Q H , + CH2=CH,
Bai 16. Hoan thanh chu6i phan umg sau :
(2)
(3)
(1)
CH.
CH3CI
A L4^3
C
CH2CI2
(5)
C 2 H 2 — ^ C4H4
(7)
^ C4H,
(8)
C4H10
t"c
5. C,H4 + H ,
6. QHfi
(4)
lU
Cao Su BuNa
^
„ „
QH4
Q-2"6
H
"'-'"^ > C,H4 + H3
7. nC,H4 - " - i ^ B ^
K'H2-CH,-f„
8. 3QH4 + 2KMn04 + 4 H : 0 -> 3C,H4(OH), + 2MnO, + 2KOH
li 18. Hoan thianh chu6i phan I'mg sau :
Hirang dan giai
CsHgCI
1. AI4C3 + 3H.O -> 4Al(OH)3 +3CH4
2. CH4 + CU
3. CH3C1 +
4. 2CH4
-» CH,C1 + H Q
a.
15(X)"C,lln
CHjQ, + HCl
> Q H , + 3H2
HgCOONa
JIL
CH.
C• 2H" 2, J I U
C2H6
11
Toluen
p - CloToluen
TNI
Sir do chudi phan liiif; hi'xi hoc UCni cir - NguySn Xu&n Trur&ng
Cty TNHH MTVDVVH Khang Vip
Hirong dan giai
1. C H j C O O N a + NaOH -> CH4 + Na.COj
2. 2CH4
l5(X)"C,lln
^ C ,2 H
"6
£
^"^'•^•'"'^ )
4.
Q6H
^6
o
C,H.,CH., + H Q
CHoCI
CH.
-> C H 2 + 3H2
3. Q H , + 2H2
4. 3 C H ,
3. C , H , + C H , C I
O
+ CI.
5. CftH,CH, + 2KMn04 + H , 0
5. Q H , + CU
QHsQ
6. QH« + C H 3 C I
6. CfiH.COOK + HCI
+ HCI
> QH,CH3
CH,
8. 3 C , H .
CH,
l"C
' ^ > C , H , C O O K + 2Mn02 + K O H
> C^HsCOOH + K C l
7. C a C , + 2 H , 0
+ HCI
+ HCI
> Ca(OW). + CM.
--^^^ C . H .
ft()()"C
7.
NO2
H2S04d
+ 3HNO3
+
Bai 20. Hoan thanh chu6i phan ling sau :
3H2O
C^Ag.
NO,
CH,
8.
o
CH,
+ cu
o
Fe, t^C
CaC.
+ HCI
CH,
^ — C,H,CI
I' .
CoH
2114
7=^
CI
(1)
n - Hexan
1. C a C . + 2 H . O
Benzyl Clorua
t(2)
CgHg
,4,
3. C^Ag, + 2HC1 —
T o l u e n - i ^ Kali b e n z o a t - ^ axit Benzoic
.ii.A...t.,:t.u..^.f ,,
., ,,„ V
A.>;.J,.,w;:-,,.
...It:.
:^„.;..;.
AljUw^ii.
Hurang dan giai
1.
2.
CH3CH2CH2CH2CH2CH3
f^l
+ 3HNO3 -
i
^
. k . ......
9
NO2
7. C H , + HCI
, NO2
8. nCH,=CHCl
3H2O
> C , A g , + 2NH4NO3
C3H. + 2AgCl
C3H4
5. C,H4 + HBr
+ 4H2-
!
+
>
4. C H 3 + H ,
> C.H^Br
6. CjHsBr + K O H
'"•'"^„
l
> Ca(OH): + C H ,
2. C , H , + 2 A g N O , + 2NH3
tw
(3)
(3)J
C.H^Br
Hirong dan giai
Bai 19. Hoan thanh chu6i phan ung sau :
TNB
PVC
> CM, + K B r + H3O
"'^^'2 > CH2=CHC1
xi,p.t"C
->
-fCHj-CHCl^^
Hp
.G
SatAchuSiphJH
ihtghda kpcHttu or- Nguyin Xu&n Trudmg
Bai 21. Hoan thanh chudi phan ung sau :
C2H4
(2)
4.
C2H6
P/tiftrnf! (in
A : CM,
(5)
C6H6
2. 3 Q H ,
C4H10
2.
5. 2CH4
i,
Bai 23.
xt.t"C
^
C3H4 +
CHe
Hoan thanh chu6i phan ting sau : (chudi hinh con ca)
"g'^'^-'" ) H2C = C H - C H 2 - C H 3
C,H4 + H .
Bai 22.
Ni,l' - > H 3 C - C H 2 - C H 2 - C H 3
'^'•'"^ > QH4
6. C H 3 - C H 2 - C H = CH2 + H2
7.
^H2C = C H - C H = CH2+H2
H2C=CH-CH2-CH3
4. C4H 10
> Q H , C H , + HCl
-»>H2C = C H - C H 2 - C H 3
3. H2C = C H - C H = C H 2 + H 2
"'-'"^ ) Q H ,
4. CM. + H,
-II
H2S04.
> Q H j + Ca(OH),
3. QHs + CH3CI
2
D: C4H10
Hirong dan giai
1. CaC, + 2H,0
-> H3C - CH2 - CH2 - CH3
C: C4He
(6)
C6H5CH3
Ni,t'
B: C4H8
C4H8
(3)
HC = C - C H = CH2
Ni.l"
>CH3-CH2-CH2
xl,t"C
Hirorng dan giai
Phuffng an 1
A : C4H,
B: C4H,
Hoan thanh chu6i phan ung sau : (chu6i hinh vudng)
C: C4H10
(2)
(4)
D
D: CM,
E: CH4
F: CM.
».
(3)
1. CH2 = C H - C H 2 - C H 3 + H2
t".Pd • > C H 3 - C H 2 - C H 2 - C H 3
k 2. CH2 = CH - CH = CH2 + 2H2
Ni.t" ->.CH3-CH2-CH2-CH3
Hirong dan giai
Phuffng an I
A : QH,o
B:CH4
^
C: CH3
D: QH4
3. C 4 H
1. C4H,o
2. C,H4
4.
"•'"'^ > QH4 + C H ,
"'''"^ > C2H, + H ,
3. 2HOCH
xl,l"C
^
H C s C - C H = CH.
I.
->C2H,+C2H,
XI. I*
->CH4+C3H,
10
C,H,„
5. C2H,
16.
xt.l
2CH4
>C2H2+2H2
>C2H2+3H.
* I
Set
ad chuSiphdn ihtg hda
hgc Huu <••'
\i-uyin
XuSn Trurdrng
PItirang an 2
3.
A : C,H,
B:
C,H4
C,H,2-^^^C,H,+3H2
XI,t"
4. C7H 16
C: C,Hs
D: CH4
E: C H 4
-^C3H,+C,H
10
5. C . H ^ - ^ ^ q H . + q H ,
F: Q H ,
6.
1. C H 2 = C H - C H 3 + H 2 - ^ ^ ^ ^ C H 3 - C H 2 - C H 3
2. C H S C - C H 3 + 2 H 2
)CH3-CH2-CH3
3. C3H^
)CH^+C2H^
4. C^H^
)CH^+C2H^
5. 2 C H ^
>C^n^+3H^
C2H,-^^C2H2+2H2
7. 3 C , H ,
XI,I'
->C.H,
Bai 25. Hoan thanh chu6i phan ling sau :
a6n" 12
5
6. C ^ H ^
2
metan
Butan
1
*• A
PE
B
Viny! axetilen — ^
>C2H2+H2
Poiibutadien
Polivinyl etilen
Bai 24. Hoan thanh chu6i phan irng sau : (chu6i hinh mui
Hirong dan giai
C
' 1 . QH,o
> Q H , + CH4
15(X)''
2. 2CH,
3. C H ,
-H
-^C2H2+3H2
QH4
H,
4. nC2H4
"'•'"•'^
3C,H.
^•'"•P
>-K:H2=CH2^„
Hiro'ng dan giai
5.
)
QH,
B:C,He
C: QH|2
6. 2C,H,
D: C4H,o
7. C H , = C H - C H C H + H ,
xt,t>
-)• C4H4
^'^"^^^
> C H 2 = C H - C H = CH2 '
E: QHft
g
G: Q H ,
nCH2-CH-CH = CH2-^J^-fCH2-CH=CH-CH2>n
poiibutadien
1- C 7 H „ - ^ C 3 H , + C , H , „
9. C H , = C H - C H - C H -
2. 2C3H^
•".H2-SO4
xl,t",p
-CH, - C H -
it.
^Q^^^^
CH-CH,
„
i:
H i r i n g dan giai
Hoan thanh chu6i phan ihig sau :
Bai 26.
Trircmg hop 1.
C.H.Br4 - > Q H , - > QHe, ^ C 2 H 5 C I - » C2H4
Polietilen
C2H2Br4 + 2 Z n ^ Q H , +2ZnBr2
4
CH4
•
A <
^
lam lanh nhanh
C •^^^—•
•D
^
» Cao SU buna
F —-—• G
— * • Polipropylen
CH^CH +
(3)
nCH:=CH3
(4)
2CH=CH
H,
>
C"<^''2-NH4Ci
C^H,
l-CH.-CH.-J,,
CH=C-CH=CH, + H 3
(6)
nCH,=CH-CH=CH,
(7)
CH=C-CH=CiI,
Bai 27.
> CH,=CH-CH=CH2
—"-'"'P
> f-CH2-CH=CH-CHHn
""'^'"^ > C H 4
"''"'P
+
2CH=CH
Q H , C : H , + CI:
) QH.CH,
QH5CH=CH.
+
[-CH3-CH2-L
C4H4 - >
C4H,o ^ C H 4 ^
Polietilen
t:uCi,.NH4Ci ^ C H = C - C H = C H ,
PS
CHjCH.CH^CH,
+
HCl
QH.CHCICK:
> QH,CH=CH,
+
HCI
nC;H5CH=CH3
— ^^i^^JL-^ [ - C H - C H . ( Q H , ) - ! „
Hoan thanh chudi phan umg sau :
QH,Br4 - ' A - ^ B - > D - > E - *
Polietilen
)
+3H2
CHjCHjCH^CHj
'•"^'^'"'^ > CjH^ + CH,=CH3
"i!^"'*''''"
) f-CH:-CH2-]„
Hoan thanh chu6i phan ung :
HQ
QH^CHCICH,
Bai 28.
— ^
y
CH=C-CH=CH,
Q,H,
+ CH.Cl
> C.HsQ
) |-CH:-CH(CH,)-]„
B^l 29.
QH,
H,
C,H2Br4 + 2 Z n - » C 3 H 2 +2ZnBr2
CH2=CH-CH,
Q H ^ C H . , ^ QH5C2H4CI
>
C^H. +2ZnBr2
> C,H,C1
CH,Br4 -» C H :
nCH,=CH2
"'•'"•P
C , H 4 - > Polietilen
C . H 4 + HCl
Hiro'ng dan giai
3C3H3
C j H i C l ->• C2H5CI
Truofng hop 3.
> CH.CH.CH^CHj
+3H,
^'^v
[-CH.-CH,-],,
CjH,
nCH.=CH,
Hoan thanh chu6i phan ling sau :
CH2 - * Q H ,
+
)
^2^^4^-'"
+ HCl
C.H,C1
^ CH=C-CH=CH,
%
C H 4 + HCl
QH^Cl
(5)
(9) C H , = C H - C H ,
— ^
C2H3Br4 + 2 Z n
1"
(8) CH^CH.CH^CH,
C H j C l + HCl
Trircfng hop 2. C,H:Br4
> CH,=CH2
"•'"'P
QHft + a ,
nCH,=CH,
"^'11"'^ ) C H , + 3H,
(2)
> C,H,
QHsQ
Hiro'ng dan giai
(1) 2CH,
CH2+H,
X ^
Y -> Z -> Q H ^
Hirong dan giai
Trircmg hop 1. C , H 8 ^ CH4 ^ C^H. ^
CH3CH2CH,
2CH4
C,H,
"*
QH,
'••^'"-'''"g > CH4 + C H 4
'^'i".!!'^ > Q H , + 3 H ,
+2H2
> QH,
- ^ . ^
TrircJng ho'p 2. C^HT —*• C4H4 —• C4H10 —• QjH^
2CH=CH
^ CH=C-CH=CH,
Cua^.NH^a
Chirmig 3.
HIDROCACBON THOM
A, K I E N THirc CO BAN
CHsC-CH=CH, + 3 H ,
CH,CH,CH,CH,
> CH.CH^CHjCH,
"""'"'"'^ ) QHfi + CH2=CH,
Trircyiig hop 3. CH^COONa ^ CH4
) CH4 + Na.COj
CHjCOONa + NaOH
CH4
'-'^"""'^ ) C H , + 3 H ,
I In
C H , + 2H,
_
_
_
> CH,
Trucmg hop 4. CH4 ^ C H , — C,H4
CH4
C,H, ^ CjH,
'^'.'''"'^ )
I In
C H , + H,
CH4 + H.
I , HIDROCACBON T H O M (AREN)
1. Cong thurc Chung : C „ H 2 n - 6
2. C a u true cua phan tilr benzen
(n>6)
•
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).
Il
M6i nguyen ti> C sir dung 3 obitan lai hoa de tao lien kfi't a vdi 2 nguydn tir C
•
ben canh no va mot nguyen tir H. Sau obitan p con lai ciia 6 nguydn til C xen
jBj^phu ben vdi nhau tao thanh obitan n chung cho ca vong benzen. Nhcr vay ma
^ H P l i e n ket 7: a vong benzen tuong d6'i ben viing hom so vdi lien ket n a anken cung
I p
nhu cac hidrocacbon kh6ng no khac.
•
Mo hlnh phan tir
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
QH^
C H . +3H,
"
> CH4
j
•
hoac
) CH,
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 hiru co nhu ancol, ete, axeton va dong
thai chinh chiing cung la dung m6i hoa tan nhidu chat khac. Chang han, benzen
hoa tan brom, iot, lu\ huynh, cao su, chat beo, ... Cac aren diu la nhihig chat c6
mui nhu benzen va toluen c6 mui thom nhe, nhung c6 hai cho siic khoe nha't la
benzen.
4. Tinh chat hoa hoc
+ Phan ling the
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
46
47
