Professional Documents
Culture Documents
Ankin (Alcin)
Ankin (Alcin)
Bin so n: V H ng Thi
t gi a ho c pha sau ho c pha tr c, c nh s nh . M ch chnh l m ch cacbon c ch a lin k t ba CC, di nh t v mang nhi u nhm th hn)
Th d :
c tn cc g c hi rocacbon lin k t vo cacbon mang n i ba, r i thm ch axetilen (Coi cc g c hi rocacbon lin k t vo cacbon mang n i ba nh l cc nhm th th H c a axetilen, acetilen)
Etin Axetilen
3 4
CH CH (C2H 2)
1 2
CH 3 C CH (C3H 4)
1 2 3
Propin Metylaxetilen
4
CH3
C C CH3 (C4H6)
5 4 3
3-Metylbut-1-in Isopropylaxetilen
CH 3 CH 2
CH C C CH3
4-Metylhex-2-in Sec-butylmetylaxetilen
CH3
C CH 2 C CH
5 1
CH CH3 CH3
3,5-imetyl-3-propylhex-1-in
(C11H20)
1 2 3 4
CH3
1
C C CH 2 (C5H 8)
2 3 4 5
CH3
6
CH 3 CH3
CH3
CH C C CH CH CH3 CH 3 CH 2 (C11H20)
5-Etyl-2,6-imetylhept-3-in
Gio khoa ha h u c
Bin so n: V H ng Thi
V.4. Tnh ch t ha h c V.4.1. Ph n ng chy 0 CnH2n 2 + (3n 1)/2 O2 t nCO2 + (n 1)H2O 1 mol n mol (n 1) mol Ankin chy t o s mol H2O < s mol CO2 hay th tch hi n c nh hn so v i kh cacbonic ( o trong cng i u ki n v nhi t v p su t) V.4.2. Ph n ng c ng hi ro (Ph n ng hi ro-ha) ankin c ng hi ro (H2) ph i c n dng ch t xc tc thch h p [Ni (Niken, Nickel) hay Pt (B ch kim, Platin)] v un nng. Ankin c ng H2 t o anken, r i ankan. CnH2n 2 + H2
Ankin Hi ro
t Ni ( Pt ) , t Ni ( Pt ) ,
0 0
CnH2n
Anken (Olefin)
CnH2n
Anken
+ H2
Hi ro
CnH2n + 2
Ankan (Parafin)
+ 2H2
Hi ro (2 mol)
t Ni ( Pt ) ,
CnH2n + 2
Ankan
R-CC-R + H2
Ankin Anken Hi ro
t Ni ( Pt ) ,
R-CH=CH-R
Anken
R-CH=CH-R +
H2
Ni ( Pt ) , t 0
R-CH2-CH2-R
Ankan
Khi c H2 d (hay v a ) v ph n ng hon ton (ph n ng hi u su t 100%, ph n ng k t thc, ph n ng xong), th: R-CC-R + 2H2
Ankin Hi ro
t Ni ( Pt ) , t Ni ( Pt ) ,
0 0
t Ni ( Pt ) ,
R-CH2-CH2-R
Ankan (Parafin)
Th d : CHCH + H2
Axetilen (Etin) Hi ro
CH2=CH2
Etilen (Eten)
CH2=CH2
Etilen
+ H2
CH3-CH3
Etan
Gio khoa ha h u c
Bin so n: V H ng Thi
th propin ph n ng h t
(C3H8) Propan
t o propan.
CH3-CH2-CH3
Lu L.1. Ph n ng c ng hi ro (H2) vo ankin th ng x y ra khng hon ton. Sau ph n ng, c th thu c ankan, anken l n ankin v H2. Ch khi no gi thi t cho c H2 d hay v a v ph n ng hon ton (hi u su t 100%, ph n ng xong, ph n ng k t thc), th t t c l ng ankin c lc u m i ph n ng h t t o ankan. L.2. Mu n ph n ng ankin c ng H2 t o ra ch y u l anken th ta dng H2 khng d v dng ch t xc tc Pd/PbCO3 (ch t xc tc pala i, paladium, trn ch t mang ch cacbonat, hay pala i trn ch t mang BaSO4), un nng. R-CC-R + H2
Ankin (1 mol) Hi ro (1 mol)
Pd / PbCO3 , t
R-CH=CH-R
Anken (Olefin)
Th d : CHCH + H2
(C2H2) Axetilen Hi ro
t Pd / PbCO3 ,
0
CH2=CH2
(C2H4) Etilen
Bi t p 35 H n h p kh A g m axetilen v hi ro c th tch 3,52 lt ( 27,3C; 106,4 cmHg) c cho vo m t bnh kn c ch a m t t b t Ni lm xc tc. un nng bnh m t th i gian, thu c h n h p kh B. a. H n h p B c th g m cc ch t no? b. T kh i c a h n h p A so v i heli b ng 2. Tnh kh i l ng h n h p B. c. Trong h n h p B trn c ch a 0,01 mol m t ch t m khi t chy t o s mol n c nh hn s mol CO2; 0,9 gam m t ch t m khi t chy t o s mol n c l n hn CO2. Tnh ph n trm th tch m i kh trong h n h p B v hi u su t ph n ng axetilen c ng hi ro. (C = 12 ; H = 1 ; He = 4) S: 1,6 gam 23,08% C2H6; 7,69% C2H4; 7,69% C2H2; 61,54% H2 HS 80% Bi t p 35 H n h p kh X g m metyl axetilen v hi ro. Cho 2,464 lt h n h p X ( o 27,3C; 1,4 atm) vo m t bnh kn c ch a m t t b t Niken lm xc tc. un nng bnh m t th i gian, thu c h n h p kh Y. a. H n h p Y c th g m cc ch t no?
Gio khoa ha h u c
Bin so n: V H ng Thi
b. T kh i hi c a h n h p X so v i hi ro b ng
109 . Xc 14
nh kh i l ng h n h p
Y. c. Trong h n h p Y trn c ch a 672 mL ( ktc) m t kh m khi t chy khng t o CO2; 0,84 gam m t kh m khi t chy t o s mol n c b ng s mol CO2. Tnh ph n trm kh i l ng m i kh trong h n h p Y. Tnh hi u su t ph n ng H2 c ng hi rocacbon khng no. (C = 12 ; H = 1) S: 2,18 gam 40,37% C3H8; 38,53% C3H6; 18,35% C3H4; 2,75% H2 HS 66,67% V.4.3. Ankin c ng halogen X2 (Cl2, Br2, I2) CnH2n 2
Ankin
X2
Halogen
CnH2n 2X2
D n xu t iahalogen c a anken
CnH2n 2X2
X2
CnH2n 2 X4
D n xu t tetrahalogen c a ankan
D n xu t ihalogen c a anken
t o d n xu t tetrahalogen
R C
R'
X2
Halogen
R C C X X
R'
Ankin
X X R C C X X
Dan xuat ihalogen cua anken Halogen
R'
X2
R C C X X
R'
Neu co X 2 d: R C C
Ankin
X X
Khi cho ankin tc d ng v i halogen X2, halogen c ng vo ankin t o d n xu t ihalogen c a anken, r i halogen c ng ti p vo d n xu t ihalogen c a anken t o ra d n xu t tetrahalogen c a ankan. Ankin c ng halogen d dng, ch c n dng dung d ch halogen v ph n ng x y ra c ngay c trong bng t i. V ph n ng x y ra d , nn n u c d halogen X2, th t t c ankin ph n ng h t t o d n xu t tetrahalogen c a ankan; V ng c l i, n u c d hi rocacbon khng no th halogen ph n ng h t. Tuy nhin, n u halogen X2 thi u th sau ph n ng c th thu c ankin cn d; s n ph m c ng d n xu t
Gio khoa ha h u c
Bin so n: V H ng Thi
ihalogen c a anken, d n xu t tetrahahlogen c a ankan (s n ph m c ng n i i l n n i n). Mu n ph n ng ankin c ng brom d ng giai o n t o d n xu t ibrom c a anken th th c hi n
nhi t th p (-20C)
Th d :
1
CH CH
Axetilen
Br2
Nc Brom
CH CH Br Br Br Br Br
1,2-ibrom etilen 1,2-ibrom eten
CH CH Br Br
Br2
CH CH Br
1,1,2,2-Tetrabrom etan
1,2-ibrom etilen
Neu co nc brom d th axetilen phan ng het, tao san pham noi n: Br Br CH CH + 2Br2 CH CH
(1 mol) Axetilen (2 mol) Nc brom
Br
Br Br Br
2
1,1,2,2-Tetrabrom etan
3 1
CH3
CH
2Br2 (d)
Nc Brom
CH3
C CH Br Br
1,1,2,2-Tetrabrom propan
Lu N u cho axetilen ph n ng tr c ti p v i kh clo (Cl2) nguyn ch t th s c hi n t ng n , do c ph n ng: C2H2 + Cl2 2C + 2HCl Do c ph n ng c ng clo vo axetilen, ng i ta dng dung d ch clo. Bi t p 36 D n 1,008 lt axetilen ( ktc) qua 200 mL dung d ch Br2 0,25 M. Dung d ch brom b m t mu hon ton v c 336 mL m t kh ( ktc) thot ra. Tnh kh i l ng cc s n ph m c ng brom thu c. Cc ph n ng x y ra hon ton. (C = 12 ; H = 1 ; Br = 80) S: 1,86 gam CHBr=CHBr; 6,92 gam CHBr2-CHBr2 Bi t p 36 Cho 672 mL metylaxetilen ( ktc) qua 1,75 lt dung d ch n c brom c n ng 0,02 mol/lt. N c brom m t mu hon ton v c 308 mL m t kh thot ra ( 27,3C; 608 mmHg). Tnh kh i l ng s n ph m c ng brom thu c.
Gio khoa ha h u c
Bin so n: V H ng Thi
Cho bi t cc s n ph m c ng brom tan trong dung d ch. Cc ph n ng x y ra hon ton. (C = 12 ; H = 1 ; Br = 80) S: 1 gam CH3-CHBr=CHBr ; 5,4 gam CH3-CHBr2-CHBr2
V.4.4. Ankin c ng n c (h p n c, Hi rat ha ankin) Ankin c ng n c theo t l mol 1 : 1, c mu i th y ngn (II) sunfat (HgSO4), trong mi tr ng axit sunfuric, un nng 80C, th ch c ankin n gi n nh t l axetilen m i t o c an ehit, l an ehit axetic (CH3-CHO). Cc ankin khc c ng n c v i i u ki n nh trn ch t o xeton (ceton, R-CO-R). Ph n ng c ng HX, c ng H2O vo ankin cng theo qui t c Markovnikov gi ng nh c ng vo anken.
CH CH
1 mol Axetilen
+
1 mol Nc
H2O
HgSO4/H2SO4 , 80 C
[CH2
0
CH OH]
CH3
CH O
CH3
C CH
H2O
Nc
[CH3
C CH2] OH
CH3
C CH3 O
(Khong ben)
+
CH3
C C CH3
H2O
Nc
HgSO4/H2SO4 , 80 C
[CH3
C C OH H
CH3]
CH3
C CH2 O
CH3
(1 mol)
(Khong ben)
V.4.5. Ankin c ng HX (Hi ro halogenua) Ankin c ng hi ro halogenua (HX) kh hn c ng halogen (X2). Tc d ng c a hi ro florua (HF) vo axetilen lc u t o vinyl florua, sau t o 1,1- ifloetan.
CH CH
Axetilen
HF
, Xt
CH2
CH F
Hiro florua t
0
CH2
CH F
HF
, Xt
CH3
CH F
Vinyl florua
1,1-iflo etan
Trong k thu t t ng h p nh a polivinyl clorua (PVC), mu n i u ch vinyl clorua, ng i ta cho axetilen tc d ng v i hi ro clorua (HCl) trn xc tc th y ngn (II) clorua (HgCl2) 120 150C. N u khng c xc tc HgCl2, th c ph n ng ti p gi a vinyl clorua v i HCl t o thnh 1,1- iclo etan (CH3-CHCl2)
Gio khoa ha h u c
Bin so n: V H ng Thi
CH CH
Axetilen
HCl
CH2 CH2
CH Cl CH Cl
n
Hidro clorua
nCH2
CH Cl
Vinyl clorua
CH2
CH Cl
HCl
t , Xt
CH3
CH Cl Cl
Vinyl clorua
Hidro clorua t , Xt
0
1,1-Diclo etan
CH3
C CH
HBr
CH3
C CH2 Br Br
Propin
Hidro bromua t
0
2-Brom propen
CH3 C CH2 Br
HBr
, Xt
CH3
C CH3 Br
2,2-Dibrom propan
V.4.6. Ankin c ng r u (R-OH), c ng axit h u c (R-COOH), axit xianhi ric (acid cianhidric, HCN)
t 0 , Xt
R C CH
R' OH
R C CH2 O R'
Ete khong no
Ankin
Ru
0
R C CH
R'
C OH O
t , Xt
R C CH2 O C O R'
Ankin
Axit hu c t 0 , Xt
R C
CH
HCN
R C CN
CH2
Axetilen
Axit Xianhiric
Th d :
Gio khoa ha h u c
Bin so n: V H ng Thi
CH CH
CH3
CH2
OH
CH2
CH O CH2
Etyl vinyl ete
CH3
Axetilen
Ru etylic
+
CH CH
CH3
C OH O
Zn(CH3COO)2
CH3
C O CH CH2 O
Vinyl axetat
Axetilen
Axit axetic
CH3
C CH
CH2
CH COOH
t 0 , Xt
CH2
CH COO C
Isopropenyl acrilat
CH2
CH3
Propin Me tyl axetilen Axit acrilic Axit propenoic
CH CH
Axetilen
HCN
t 0 , Xt
Axit Xianhiric
CH CH
CH2
CH C CH (C4H4)
Vinyl axetilen
Axetilen
(2C2H2)
Axetilen
3CH CH
(3C2H2) Axetilen
C6H6
Be nze n
c.
Gio khoa ha h u c
Bin so n: V H ng Thi
n CH CH
Axetilen
CH CH
Hay: n C2H2 2
Axetilen Trung hp (t 0 Xt) ,
(CH)n
Cupren (Chat cach ien, cach nhiet)
Khi c m t b t ng (Cu) v v t oxi 200-250C, axetilen trng h p t o thnh m t polime, l cupren. y l m t ch t b t v nh hnh, kh i l ng phn t r t l n, khng tan trong n c v cc dung mi h u c. Cupren c dng lm ch t cch i n, cch nhi t.
d. Tam h p propin, thu c ch t isopren
3 CH3
CH
CH3
1
H3C
CH3
(C9H12)
R-CC-R + 3[O]
Ankin
+ H2O
dd KMnO4
dd KMnO4
R-COOH +
Axit h u c
R-COOH
Axit h u c
CHCH + 4[O]
Axetilen
HOOC-COOH
Axit oxalic; Axit etan ioic
3CHCH
Axetilen (Ch t kh )
CHCH + 2KMnO4
Axetilen Kali pemanganat (Ch t kh ) (Ch t oxi ha)
Gio khoa ha h u c
10
Bin so n: V H ng Thi
0 1
+7
+3
+4
+2
Axit axetic
+3
+3
Axit propionic
R-CCH
Ankin u m ch Ankylaxetilen
+ AgNO3 + NH3
dd B c nitrat trong amoniac
R-CCAg
NH4NO3
R-CCH
Ankin u m ch Ankyl axetilen
CuCl
NH3
R-CCCu
NH4Cl
Dung d ch
AgCCAg
+ 2NH4NO3
HCCH +
Axetilen Etin dd
2CuCl
+ 2NH3
CuCCCu
+ 2NH4Cl
ng (I) axetilua Amoni clorua Mu i ng (I) c a etin (Ch t khng tan, c mu g ch)
2CH3-CCH
Propin, Metylaxetilen
+ AgNO3 + NH3
2CH3-CCAg
+ NH4NO3
Gio khoa ha h u c
11
Bin so n: V H ng Thi
CH3-CH2-CCH
Butin 1 Etyl axetilen
+
dd
CuCl + NH3
CH3-CH2-CCCu
Mu i
+ NH4Cl
Lu L.1. Chng trnh ph thng hi n nay khng h c ph n ng gi a ankin dung d ch ng (I) clorua trong amoniac.
u m ch v i
L.2. Ankin ch a n i ba trong m ch (R-CC-R) khng tc d ng v i dung d ch AgNO3/NH3 cng nh dung d ch CuCl/NH3. Th d : CH3-CC-CH3 + AgNO3 + NH3
But-2-in ; imetylaxetilen
L.3. Ng i ta th ng dng ph n ng c trng ny nh n bi t ankin u m ch, cng nh tch l y ankin u m ch ra kh i h n h p cch ch t h u c. N u l ankin u m ch th khi cho tc d ng v i dung d ch b c nitrat trong amoniac (AgNO3/NH3) s thu c ch t khng tan c mu vng nh t. Cho h n h p cc ch t h u c c ch a ankin u m ch tc d ng v i dung d ch b c nitrat trong amoniac th ch c ankin u m ch ph n ng t o ch t khng tan c mu vng nh t. Sau l c l y ch t khng tan ny cho tc d ng v i dung d ch axit clohi ric (HCl) s ti t o c ankin u m ch.
R-CCAg R-CCH
Ankin u m ch
NH4NO3
R-CCAg
Mu i b c c a ankin
+
u m ch
HCl
Axit clohi ric
+ AgCl
B c clorua
Th d : HCCH
Axetilen
2AgNO3
+ 2NH3
AgCCAg
B c axetilua
+ 2NH4NO3
AgCCAg
+ 2HCl
Axit clohi ric
HCCH
Axetilen
+ 2AgCl
B c clorua
CH3
CH C CH + AgNO3 + NH3
CH3
CH C CAg
+ NH4NO3
CH 3 Muoi bac cua 3-metylbut-1-in Bac isopropylaxetilua CH3 CH C CH + AgCl Bac clorua
CH3 Isopropylaxetilen
Gio khoa ha h u c
12
Bin so n: V H ng Thi
Bi t p 37 Tch l y ring t ng kh ra kh i h n h p g m: metan, etilen v axetilen. Bi t p 37 Hy tch l y ring t ng ch t ra kh i h n h p g m cc kh sau y: Propan, propilen v propin. L.4. Th c ra khi cho mu i b c nitrat vo dung d ch amoniac th c s t o ph c ch t c ch a ion ph c l [Ag(NH3)2]+ tan trong dung d ch. Cng nh khi cho ng (I) clorua vo dung d ch amoniac l c s t o ion ph c [Ag(NH3)2]+ tan. Trong sch ph thng c vi t Ag2O nh m n gi n ha. Do v y ph n ng gi a ankin u m ch v i dung d ch b c nitrat c cc cch vi t khc nhau nh sau:
R-CCH + AgNO3 + NH3 R-CCAg + NH4NO3 R-CCH + Ag2O AgNO3 / 3 R-CCAg + H2O NH R-CCH + [Ag(NH3)2]+ AgNO3 / 3 R-CCAg + NH4+ + NH3 NH R-CCH + [Ag(NH3)2]NO3 AgNO3 / 3 R-CCAg + NH4NO3 + NH3 NH
AgNO3 / NH R-CCH + [Ag(NH3)2]OH 3 R-CCAg + 2NH3 + H2O
Sch ph thng (khng nng cao, chng trnh chu n) hi n nay vi t theo cch u, ngha l vi t v y. Cn sch nng cao vi t ph n ng ny theo cch cu i, d ng ph c [Ag(NH3)2]OH.
c sao
Th d : Vi t ph n ng gi a axetilen v i dung d ch b c nitrat trong amoniac theo 5 cch. HCCH + 2AgNO3 + 2NH3 AgCCAg + 2NH4NO3
dd B c nitrat trong amoniac Amoni nitrat
HCCH + Ag2O
Axetilen B c oxit
NH 3 AgCCAg + H2O
B c axetilua N c
HCCH + 2[Ag(NH3)2]NO3 AgNO3 / 3 AgCCAg + 2NH4NO3 + 2NH3 (4) NH HCCH + 2[Ag(NH3)2]OH AgNO3 / 3 AgCCAg + 4NH3 + 2H2O NH Th d khc: Vi t ph n ng gi a propin v i dung d ch b c nitrat trong amoniac theo 5 cch. (5)
Gio khoa ha h u c
13
Bin so n: V H ng Thi
Ag2O
(5)
Th d t lm: Vi t ph n ng gi a isopropyl axetilen v i dung d ch b c nitrat trong amoniac theo cc cch khc nhau.
L.5.
thi tuy n sinh i h c hi n nay do B Gio D c v o T o ra chung cho c n c, theo st chng trnh sch gio khoa ph thng. Do o chng ta nn theo cch vi t ph thng khi lm bi. Nh v y trong 5 cch trn, n u h c theo chng trnh chu n (khng nng cao), th chng ta vi t theo cch (1). Theo chng trnh nng cao th vi t theo cch (5).
Bi t p 38 Ch t A c CTPT C10H10. Cho 2,6 gam ch t A tc d ng hon ton v i l ng d dung d ch AgNO3/NH3, thu c 9,02 gam m t ch t khng tan c mu vng nh t. Xc nh CTCT c a A. Bi t r ng khi hi ro ha hon ton A th thu c ch t 4-etyl-3metylheptan. (C = 12 ; H = 1 ; Ag = 108) Bi t p 38 X l m t hi rocacbon c CTPT C12H16. em 2,4 gam ch t X tc d ng v i l ng d dung d ch b c trong amoniac, ph n ng xong, thu c 5,61 gam m t ch t khng tan c mu vng nh t. N u em kh hon ton ch t X b ng H2 th thu c ch t 1-etyl-4-butyl xiclohexan. Xc nh CTCT c a X. Vi t cc phng trnh ph n ng x y ra. (C = 12 ; H = 1 ; Ag = 108) V.5. ng d ng V.5.1. Axetilen PVC
CH CH
Axetilen
+
HCl
, Xt
CH2
CH Cl
Axit hiric
n CH2
CH Cl
CH2
CH Cl n
Vinyl clorua
Gio khoa ha h u c
14
Bin so n: V H ng Thi
V.5.2.
Axetilen
CHCH + HCCH
Axetilen Axetilen
Vinylaxetilen
0
CH2=CH-CCH + H2 Pd , CH2=CH-CH=CH2 t
Vinyl axetilen Hi ro Buta-1,3- ien
n CH2=CH-CH=CH2 TH (-CH2-CH=CH-CH2-)n Na
Buta-1,3- ien
TH Na
Cao su buna
CH2
CH CH2 CN n
nCH2
TH Na
CH2
CH CH CH2
CH CH2 n
Buta-1,3-ien CH2 CH C CH
Cao su buna-S
1
CH2
CH C CH2 Cl
Hiro clorua TH Na
Axetilen Vinyl axetilen n-Butan Propen R u isopropylic Axeton 2-Metylbut-3-in-2-ol 2-Metylbut-2-en-3-in Isopren Cao su isopren CHCH + CHCH
Axetilen Vinyl axetilen Axetilen
Nh h p (t , Xt)
CH2=CH-CCH
Vinyl axetilen
CH2=CH-CCH + 3H2
Hi ro
Ni ,t 0
CH3-CH2-CH2-CH3
Butan; n- Butan
CH3-CH2-CH2-CH3
n-Butan
, Xt Cracking (t ,
CH4
Metan
+ CH2=CH-CH3
Propen (Propilen)
Gio khoa ha h u c
15
Bin so n: V H ng Thi
CH2 CH
Propen
CH3
H2O
N c
H3PO4, t , p (H2SO4(l), t 0 )
CH3
CH CH3 OH
R u isopropylic
CH3 CH CH3
R u isopropylic
CuO
CH3
C CH3 O
Cu
o ng
H2O
N c
OH
o ng (II) oxit
CH CH
Axetilen
CH3
C CH3 O
Axeton
, Xt
(KOH)
CH C C CH3 OH
2-Metylbut-3-in-2-ol
CH3
(Phan ng Favorski)
CH3 CH C C CH3 OH
2-Metylbut-3-in-2-ol
4 3 2 1
CH C C CH2
2-Metylbut-1-en-3-in
H2O
CH3
CH C C CH2
2-Me tylbut-1-en-3-in
H2
Pd , t 0
CH2 CH C CH2
Isopren Butaien-1,3
CH3
CH3
n CH2 CH
C CH2 CH3
TH Na
CH2
CH C CH2 CH3 n
Isopren
Cao su isopren
V.5.3. Ankin Anken Khi cho ankin tc d ng hi ro dng ch t xc tc l h n h p Pd/PbCO3 ho c Pd/BaSO4, un nng, th ankin ch c ng m t phn t hi ro t o anken tng ng.
R-CC-R +
Ankin
H2
Hi ro
R-CH=CH-R
Anken (Olefin)
Th d : CHCH + H2
Axetilen Hi ro
CH2=CH2
Etilen
CH3-CCH + H2
Propin Hi ro
CH3-CH=CH2
Propen
V.5.4. Axetilen
3 CH CH ( 3C2H2 )
Axetilen
Benzen
Tam h p C , 600 C (Than ho at tnh) Benzen
0
(C6H6)
Gio khoa ha h u c
16
Bin so n: V H ng Thi
V.5.6. Axetilen Nh a phenolfoman ehit Axetilen An ehit axetic Axit axetic Natri axetat Metan Foman ehit Axetilen Benzen Clobenzen Phenol Nh a phenolfoman ehit
CH CH
Axetilen
+
N c
+
H2O
1 2
HgSO4/H2SO4 80 0 C
2+
CH2 CH3
CH
OH
CH3
CH O
(Kho n g be n)
Anehit axetic
CH3
CHO
O2
Mn
COOH
Anehit axetic
Axit axetic
CH3 CH3
COOH
NaOH
Xu t
+
CH3
Axit axetic
Natri axetat
COONa CH4
Me tan
N c
+
H2O
Natri axetat
+
COONa (r) O2
NaOH (r)
Vo i to i-Xu t t0
Na2CO3
Xoa (Soda)
CH4
Metan
HCHO
Fomanehit
N c
H2O
3 C2H2
Axetilen
(C6H6)
Be nzen Fe (FeCl3)
Cl
+
Cl2
Clo
HCl
Hiro clorua
(C6H6)
Bezen
(C6H5Cl)
Clobenzen Phenyl clorua
Cl
+
OH NaOH()
Xu t (a c) t
0
,p (C6H5OH)
Phenol
NaCl
Natri clorua
(C6H5Cl)
OH (n + 2) (C6H5OH)
Phenol
+
OH (n + 1) HCHO
Fomanehit Tru n g ngng ( t , Xt )
0
OH CH2 CH2 n
Nh a phenol fomanehit
+
OH
(n + 1) H2O
N c
Gio khoa ha h u c
17
Bin so n: V H ng Thi
Hay:
OH n
Phenol Nh a phenolfomanehit
+
OH n HCHO
Fomanehit TN (t , Xt)
0
CH2 n
n H2O
N c
CH3-CHO
An ehit axetic
CH3-CHO
An ehit axetic
1 O2 2
Mn
2+
CH3-COOH
Axit axetic
CH2=CH-CN
Nitrin acrilic; Acrilonitrin; Acrilonitril
V.5.9. Axetilen PVAc , PVA Axetilen An ehit axetic Axit axetic Vinyl axetat Polivinyl axetat (PVAc) Polivinyl ancol (PVA)
CHCH + H2O
Axetilen N c
C HgSO4 80
CH3-CHO
An ehit axetic
CH3-CHO
An ehit axetic
1 O2 2
Mn
2+
CH3-COOH
Axit axetic
CH3-COOH + CHCH
Axit axetic Axetilen
, Xt Zn CH COO ) 2 t ((3 )
CH3-COO-CH=CH2
Vinyl axetat
n CH3
C O CH CH2 O
(t
TH
0
, Xt)
CH CH2 O C CH3 O n
Polivinylaxetat (PVA c)
Vinyl axetat
CH CH2 O C O CH3 n
+ n NaOH (dd)
dd X ut
CH CH2 OH n
Polivinylancol (PVA ) R u polivinylic
+ n CH3COONa
Natri axetat
V.5.10. Axetilen cn c dng gi tri cy cho mau chn; dng trong hn gi ; dng th p sng ( n kh ); bm bong bng bay;
Gio khoa ha h u c
18
Bin so n: V H ng Thi
V.6.
V.6.1. T
a voi Than a CaCO 3
A xetilen
CaO
Vo i so ng Canxi oxit
a vo i Canxi cacbonat
Kh cacbonic
CO 2
Than a CaO
Vo i so ng
+
Chng ca t (trong lo co c)
3C
Than co c
a t e n Canxi cacbua
CaC2
Cacbon oxit
CO
Canxi cacbua
CaC2
2H2O
N c
C2H2
Axetilen
Ca(OH)2
Canxi hiroxit
+
CaC 2
2HCl
C2H2
Axit clohiric
Canxi clorua
CaCl2
C2H2
Axetilen
3 H2
Hiro
2 Zn
Bo t ke m
R C C
Ankin
R'
2 ZnX2
Ke m halogenua
Th du: Br
1
Br
2
CH CH Br Br
2 Zn
Ke m
CH CH
Axetilen
2 ZnBr2
Ke m bromua
1,1,2,2-Tetrabrom etan
Cl Cl
2
CH3
C C Cl Cl
CH3
2 Cl2
Clo
CH3
C C CH3
Butin -2
2 NaCl
Natri clorua
2,2,3,3-Tetraclobutan
Lu
Gio khoa ha h u c
19
Bin so n: V H ng Thi
Ng i ta th ng dng phng php i u ch ny tch l y ankin (ch y u l ankin gi a m ch) ra kh i h n h p cc ch t h u c. Cho h n h p cc ch t h u c, c ch a ankin, tc d ng v i n c brom d. Ankin ph n ng t o s n ph m c ng brom b gi l i trong dung d ch. Sau cho b t k m vo s n ph m c ng brom, s ti t o c ankin.
Bi t p 39 imetyl axetilen c l n metan v propan. Hy tinh ch
imetyl axetilen.
Bi t p 39 Hy tch l y ring t ng kh ra kh i h n h p g m cc kh sau y: Butan, But-2-in v Cacbon ioxit. V.6.4. D n xu t , - ihalogen hay , - ihalogen c a ankan tc d ng v i KOH trong r u (ancol), un nng Ankin
R CH CH R' X X
+
2 KOH
Kali hiroxit
R u t0
R C C
Ankin
R'
2 KX
2 H2O
Kali halogenua
N c
R CH2 CH X X
2 KOH
R C CH
Ankin
2 KX
2 H2O
Th d :
CH2 Br CH2 Br + 2KOH
R u t0
CH CH
Axetilen
+ 2KBr
2H2O
1,2-ibrom etan
CH3
CH2 CH Br Br
2KOH
R u
t0
CH3
C CH
+ 2KBr + 2H2O
1,1-ibrom propan
Lu Ng i ta th ng v n d ng phng php i u ch ny chuy n ha m t anken thnh ankin tng ng. Cho anken tc d ng v i n c brom (dung d ch brom), anken ph n ng t o s n ph m c ng brom. Sau cho s n ph m c ng brom ny tc d ng v i KOH trong r u, un nng, s thu c ankin tng ng. Bi t p 40 Vi t phng trnh ph n ng chuy n ha qua l i gi a etilen v i axetilen. Bi t p 40 Vi t phng trnh ph n ng i u ch qua l i gi a propen v i propin.
Gio khoa ha h u c
20
Bin so n: V H ng Thi
Ankin
R-CCAg
B c axetilua
HCl
R-CCH
Ankin u m ch
AgCl
B c clorua
Th d : AgCCAg
B c axetilua
+ +
2HCl HCl
HCCH
Axetilen
2AgCl
B c clorua
CH3-CCAg
B c metylaxetilua
CH3-CCH
Propin
AgCl
B c clorua
Lu Ng i ta th ng dng phng php i u ch ny tch l y ring ankin u m ch ra kh i h n h p cc ch t h u c. Cho h n h p cc ch t h u c, c ch a ankin u m ch, tc d ng v i dung d ch b c nitrat trong amoniac. Ankin u m ch ph n ng, t o mu i b c c a ankin u m ch. Mu i ny khng tan, c mu vng nh t. L c l y ch t khng tan ny cho tc d ng v i dung d ch axit clohi ric, s ti t o c ankin u m ch. Bi t p 41 H n h p kh A g m metan, etilen v axetilen. Hy dng phng php ha h c tch l y ring m i ch t ra kh i h n h p A. Bi t p 41 H n h p X g m cc kh: etan, propin v imetylaxetilen. Hy tch l y ring m i kh ra kh i h n h p X. Bi t p 42 H n h p A g m hai ankin hn km nhau m t nhm metylen trong phn t . Cho 6,6 gam h n h p A h p th vo l ng d dung d ch b c nitrat trong amoniac, thu c 38,7 gam ch t r n khng tan, c mu vng nh t. Khng cn hi rocacbon sau ph n ng. a. Xc nh cng th c hai ankin trn. b. Tnh ph n trm kh i l ng m i ch t trong h n h p A. c. N u un nng h n h p A trong bnh kn v i ch t xc tc thch h p, thu c hai hi rocacbon tng ng, c c u t o cn x ng. Xc nh hai hi rocacbon ny v c tn chng. Hy cho bi t cc s n ph m ph c th c. (C = 12 ; H = 1 ; Ag = 108) S: 39,39% C2H2 ; 60,61% C3H4 c. Benzen, Mesitilen (Vinyl axetilen; Cupren; 2-metylPent-1-en-3-in; Poli metylaxetilen) Bi t p 42 H n h p A g m hai ankin u m ch lin ti p (khng c axetilen). Cho 3,22 gam h n h p A tc d ng hon ton v i l ng d dung d ch AgNO3/NH3, thu c 10,71 gam ch t r n mu vng. a. Xc nh CTPT, CTCT v tn c a hai ankin trn.
Gio khoa ha h u c
21
Bin so n: V H ng Thi
b. Tnh kh i l ng m i ch t trong 3,22 gam h n h p A. c. Trng h p ankin c kh i l ng phn t nh trong h n h p A, thu c m t hi rocacbon thm B. Vi t phng trnh ph n ng t o B v ph n ng gi a B v i dung d ch KMnO4, bi t r ng c t o mu i c a axit a ch c thm, ng th i c t o ch t r n mu en. (C = 12 ; H = 1 ; Ag = 108) S: 1,6 gam CH3-CCH ; 1,62 gam CH3-CH2-CCH
CU H I N PH N V
1. Ankin l g? Hy cho bi t cng th c t ng qut c a ankin. 2.
a.
c tn cc ch t sau y:
CH3 C C CH CH3 CH3 b. CH3 CH3 CH2 CH2 C CH2 CH CH3 C CH CH3 CH3 CH3 CH CH C CH CH C CH CH3 d. CH2 CH CH2 C CH
c.
a. 3,4,4-Trimetylpent-1-in c. Alylvinylaxetilen
b. 6-Etyl-7-metyl-4-propyl-3-isopropyloct-2-en d. Sec-butylisopropylaxetilen
4. A l m t ch t h u c thu c dy ng ng ankin. t chy 0,5 mol A, thu c 2 mol CO2. A tc d ng c dung d ch b c nitrat trong amoniac. Xc nh CTCT v c tn A. Vi t cc phng trnh ph n ng x y ra. S: But-1-in 5. X l m t hi rocacbon. M t th tch hi X v i 4,875 th tch kh metan c cng kh i l ng (cc th tch kh, hi o trong cng i u ki n v nhi t v p su t). Cho 7,8 gam X tc d ng h t v i dung d ch b c nitrat trong amoniac, thu c 29,2 gam ch t r n khng tan, c mu vng. Xc nh CTCT c a X. Bi t r ng X c c u t o m ch h , phn nhnh. (C = 12 ; H = 1 ; Ag = 108) 6.
t chy hon ton 4 gam ch t h u c A. S n ph m chy ch g m 6,72 lt CO2 ( ktc) v 3,6 gam H2O. T kh i hi c a A nh hn 1,5. Xc nh CTCT c a A. Vi t phng trnh ph n ng c a A v i: H2 (c Ni lm xc tc, un nng); N c brom (d); N c brom (thi u); Dung d ch KMnO4 (trong mi tr ng axit H2SO4); Dung d ch KMnO4 (trong mi tr ng trung tnh H2O); H2O (t mol 1 : 1, c mu i
Gio khoa ha h u c
22
Bin so n: V H ng Thi
Hg2+ lm xc tc, 80C); HCN (t l 1 : 1, c ch t xc tc, nhi t thch h p); Ph n ng tam h p A; Ph n ng trng h p ( a h p) A; Ph n ng chy c a A; Dung d ch AgNO3/NH3. Cho bi t A tc d ng c dung d ch b c nitrat trong amoniac. (C = 12 ; H = 1 ; O = 16)
7. H n h p A g m hai ankin c kh i l ng phn t hn km nhau 14 vC. Cho bi t 3,82 gam h n h p A lm m t mu v a dung d ch brom c ha tan 16 gam brom. S n ph m thu c ch g m lin k t n. a. Xc nh CTPT c a hai hi rocacbon trong h n h p A. b. Tnh % s phn t gam m i ch t trong h n h p A. c. Xc nh cc CTCT c th c c a hai ankin trn. c tn m i ch t. Cho bi t hai ch t trong h n h p A u c c u t o m ch th ng. (C = 12 ; H = 1 ; Br = 80) S: 40% C5H8; 60% C6H10 8. Vi t phng trnh ph n ng theo s sau y (m i mi tn l m t ph n ng): Metan Axetilen An ehit axetic Axit axetic Natri axetat Metan Foman ehit R u metylic An ehit fomic Axit fomic Metyl fomiat Natri fomiat Hi ro Amoniac Nit oxit Nit ioxit Axit nitric. 9. H n h p X g m ba kh l metan, etilen v axetilen. N u t chy h t 3,36 lt h n h p X ( ktc) r i cho s n ph m chy h p th vo n c vi d th thu c 24 gam k t t a. Cn n u l y 13,6 gam h n h p X cho tc d ng v i l ng d dung d ch b c nitrat trong amoniac th thu c 38,4 gam k t t a. Xc nh % kh i l ng m i ch t trong h n h p X. Cc ph n ng x y ra hon ton. (C = 12 ; H = 1 ; Ag = 108 ; Ca = 40 ; O = 16) S: 28,23% CH4 ; 41,18% C2H4 ; 30,59% C2H2 10. T CH4, NaCl, H2O v khng kh (ch t xc tc c ), hy vi t phng trnh ph n ng i u ch : Polivinyl axetat v axit picric (2,4,6-trinitrophenol). ( TS H, i h c S Ph m v i h c Lu t tp HCM, nm 2001) 11. Vi t phng trnh ph n ng theo s
Cn H 2n+2 A2
Cl2, askt , 1 : 1 (1)
0
sau:
A2 A5
(3)
A1
(2)
A3
0
A4
dd KMnO4 (5)
A6
(7)
A3
A1, A6 co cung so nguyen t cacbon trong phan t A6 cho c phan ng trang gng va ot chay 1mol A 6 thu c 2mol CO 2
12. H n h p Z g m 0,15 mol CH4; 0,09 mol C2H2 v 0,2 mol H2. Nung nng h n h p Z v i xc tc Ni thu h n h p Y. Cho Y qua dung d ch brom d thu c h n h p
Gio khoa ha h u c
23
Bin so n: V H ng Thi
kh A c phn t l ng trung bnh l 16. tng kh i l ng dung d ch brom l 0,82 gam. Tnh s mol m i ch t trong A. (C = 12 ; H = 1 ; Br = 80) ( TS H, i h c Qu c gia tp HCM, nm 2001) S: 0,15 mol CH4; 0,06 mol C2H6; 0,06 mol H2
13. X v Y l hai hi rocacbon c cng CTPT l C5H8. X l monome dng trng h p thnh cao su isopren; Y c m ch cacbon phn nhnh v t o k t t a v i dung d ch NH3 c Ag2O. Hy cho bi t CTCT c a X v Y. Vi t cc phng trnh ph n ng x y ra. ( TS H, nm 2002) 14. Ch t A c cng th c phn t l C7H8. Cho A tc d ng v i Ag2O (d) trong dung d ch amoniac c ch t B k t t a. Kh i l ng phn t c a B l n hn c a A l 214 vC. Vi t cc CTCT c th c c a A. (Ag = 108 ; H = 1) ( TS H kh i B, nm 2003) S: 4 CTCT 15. Cho h n h p A g m 0,3 mol C2H2 v 0,6 mol H2 i qua ng s ch a Ni, un nng. Thu c h n h p kh B. D n h n h p B qua bnh ng n c brom c d. Bnh brom tng thm m gam, c 8,96 lt h n h p kh C thot ra ( ktc) kh i bnh n c brom, trong C khng c hi n c. T kh i h n h p C so v i kh heli b ng 3,125. Tr s c a m l: a) 2 gam b) 4 gam c) 6 gam d) 5 gam (C = 12; H = 1; He = 4) 16. X l m t hi rocabon c CTPT C10H6. Cho 12,6 gam X tc d ng hon ton v i l ng d dung d ch b c nitrat trong amoniac, thu c 34 gam m t ch t r n mu vng nh t. Phn t X c ch a: a) 4 lin k t ba CC u m ch b) 3 lin k t ba CC u m ch c) 2 lin k t ba CC u m ch d) 1 lin k t ba CC u m ch (C = 12; H = 1; Ag = 108) 17. Cho 2,912 lt metylaxetilen ( ktc) l i qua 1,4 lt dung d ch Br2 0,1 M. T t c brom m t mu h t. C 672 mL m t kh ( ktc) thot ra kh i bnh n c brom. Kh i l ng s n ph m c ng brom thu c l: a) 26,4 gam b) 34,4 gam c) 50,4 gam d) T t c u khng ng (C = 12; H = 1; Br = 80) 18. H n h p A g m canxi cacbua v natri hi rua. Cho 11,2 gam h n h p A tc d ng hon ton v i l ng n c d, thu c h n h p B g m hai kh. Cho l ng h n h p B qua ng s c Ni lm xc tc, un nng, thu c m t ch t D duy nh t. D khng lm m t mu dung d ch KMnO4. Thnh ph n ph n trm kh i l ng m i ch t trong h n h p A l: a) 28,57%; 71,43% b) 68,57%; 31,43% c) 51,43; 48,57% d) 57,14%; 42,86% 19. A l m t hi rocacbon m 1 mol A c ng c 2 mol H2 t o ankan tng ng. Khi t chy 1 mol A th thu c 5 mol CO2 v khi cho A tc d ng v i dung d ch AgNO3
Gio khoa ha h u c
24
Bin so n: V H ng Thi
Kh i l ng cao su thu c theo s trn n u dng 1000 m3 metan ( ktc) lc l: A. 729 kg B. 364,50 kg C. 91,13 kg D. 182,25 kg (C = 12; H = 1)
23. em nung nng m t l ng kh metan 1500C r i lm l nh nhanh, thu c h n h p kh A g m axetilen, hi ro v metan cha b nhi t phn. T kh i c a A so v i oxi b ng 0,3. Hi u su t ph n ng nhi t phn metan l: A. 66,67% B. 70% C. 83,33% D. 90% (C = 12; H = 1; O = 16) 24. A l m t ankin. Khi t chy a mol A, thu c 6a mol CO2. A c th c bao nhiu cng th c c u t o? A. 5 B. 6 C. 7 D. 8 25. H n h p kh A g m etan, etilen v axetilen. D n 13,44 lt h n A qua l ng d dung d ch brom th c 6,72 lt kh thot ra. Cn n u cho cng l ng h n h p A trn qua l ng d dung d ch AgNO3 trong NH3 th thu c 24 gam k t t a. Ph n trm kh i l ng m i ch t trong h n h p A l: A. 50%; 33,33%; 16,67% B. 52,32%; 32,56%; 15,12% C. 17,44%; 33,33%; 49,23% D. 31,15%; 27,48%; 41,37% (C = 12; H = 1; Ag = 108) 26. A l m t ch t h u c m khi t chy ch t o CO2 v H2O. em t chy h t 5,2 gam A, r i d n s n ph m chy l n l t qua bnh (1) ng P2O5 d v bnh (2) ng n c vi d. Kh i l ng bnh (1) tng 3,6 gam. Trong bnh (2) c 40 gam k t t a. A tc
Gio khoa ha h u c
25
Bin so n: V H ng Thi
d ng dung d ch AgNO3 trong NH3 t o k t t a mu vng nh t. T kh i hi c a A l n hn 0,9 nhng nh hn 2,6. A l: A. Axetilen B. Metylaxetilen C. Vinylaxetilen D. A l h p ch t c ch a O v phn t c ch a lin k t ba CC u m ch (C = 12; H = 1; O = 16; Ag = 108; Ca = 40) 27. H n h p A g m 0,15 mol axetilen v 0,3 mol hi ro. D n h n h p qua ng s ng Ni xc tc, un nng, thu c h n h p kh B g m etan, etilen, axetilen v hi ro c kh i l ng phn t trung bnh b ng 18. Hi u su t ph n ng c ng hi ro l: A. 66,67% B. 60% C. 83,33% D. 85% (C = 12; H = 1) 28. A l m t hi rocacbon. Hi ro ha A, thu c hexan. Khi cho 0,02 mol A tc d ng h t v i dung d ch AgNO3/NH3 th thu c 5,84 gam k t t a. Cng th c c a A l: A. CH3CH2CH2CH2CCH B. CH3CCCH2CCH C. CH2=CHCH2CH2CCH D. HCCCH2CH2CCH (C = 12; H = 1; Ag = 108) 29. A l m t ch t c cng th c th c nghi m (C3H2)n. Hi ro ha A, thu c hexan. N u cho 3,8 gam A tc d ng hon ton v i l ng d dung d ch AgNO3 trong NH3 th thu c 9,15 gam k t t a mu vng nh t. Cng th c c a A l: A. HCCCH=CHCCH B. CH2=CHCCCCH C. CH2=C=CHCH2CCH D. HCCCH2CCCH3 (C = 12; H = 1; Ag = 108) 30. H n h p A g m hai ch t h u c d ng kh lin ti p trong dy ng ng ankin. Qua th nghi m cho th y 5,1 gam A tc d ng v a dung d ch brom c ha tan 0,22 mol brom t o d n xu t tetrabrom c a ankan. Ph n trm th tch m i ch t trong h n h p A l: A. 54,55%; 45,45% B. 33,33%; 66,67% C. 40%; 60% D. 63,64%; 36,36% (C = 12; H = 1) 31. Th c hi n ph n ng trng h p 224 lt kh axetilen ( o 27,3C; 836 mmHg), thu c 208 gam cupren, l m t polime c dng lm ch t cch i n, cch nhi t. Hi u su t ph n ng trng h p axetilen l: A. 60% B. 70% C. 80% D. 90% (C = 12; H = 1) 32. Ng i ta th c hi n ph n ng tam h p axetilen t o benzen b ng cch un nng bnh kn ng kh axetilen, c b t than lm xc tc, 600C. Sau khi a nhi t bnh v nh lc u. Coi th tch bnh khng thay i, ch t xc tc v benzen l ng t o ra chi m th tch khng ng k , ng i nh n th y p su t trong bnh gi m 2,5 l n so v i tr c khi ph n ng. Hi u su t ph n ng i u ch benzen t axetilen l: A. 90% B. 85% C. 70% D. 60% 33. T vi c th i u ch nh a PVC (poli vinyl clorua) theo s : vi HS % Vi s ng HS % 90 80 HS 100% Canxi cacbua Axetilen HS % Vinyl clorua HS % PVC 70 85 Kh i l ng vi ch a 80% CaCO3 c n dng s n xu t c 2 t n PVC l: A. 7,47 t n B. 5,976 t n C. 9,337 t n D. 6,15 t n (Ca = 40; C = 12; O = 16; H = 1; Cl = 35,5)