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Gio khoa ha h u c

Bin so n: V H ng Thi

V. ANKIN (ALKYNE, ALCYNE, AlCIN, DY NG NG AXETILEN)


V.1. nh ngha Ankin l m t lo i hi rocacbon m trong phn t c ch a m t lin k t ba, m ch h .

V.2. Cng th c t ng qut CnH2n 2 (n 2)

V.3. Cch c tn (Danh php) - Ankan Ankin (C thm s ch v tr c a lin k t ba,

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

But-2-in CH C CH CH3 Butin-2 CH 3 2-Butin (C5H8) imetylaxetilen


2 1

3-Metylbut-1-in Isopropylaxetilen

CH 3 CH 2

CH C C CH3

CH3 (C7H 12) CH3 CH 2 CH 2


3 2

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

Pent-2-in; Pentin-2; 2-Pentin Etylmetylaxetilen


7

CH 3 CH3

CH3

CH C C CH CH CH3 CH 3 CH 2 (C11H20)

5-Etyl-2,6-imetylhept-3-in

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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)

Khi c H2 d hay v a ng h t t o ankan. CnH2n 2


Ankin (1 mol)

v ph n ng hon ton (hay hi u su t 100%) th ankin m i ph n

+ 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

N u c H2 d (hay v a ) v ph n ng hon ton th axetilen ph n ng h t v t o ra etan: t0 CHCH + 2H2 Ni ( CH3-CH3 Pt ) ,


(C2H2) Axetilen Hi ro (C2H6) Etan

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Bin so n: V H ng Thi

t CH3-CCH + H2 Ni ( CH3-CH=CH2 (Propen; Propilen) Pt ) , t0 CH3-CH=CH2 + H2 Ni ( CH3-CH2-CH3 (Propan) Pt ) ,

N u ph n ng hon ton v c H2 d hay v a CH3-CCH + 2H2


Hi ro
Ni ( Pt ) , t 0

th propin ph n ng h t
(C3H8) Propan

t o propan.

CH3-CH2-CH3

(C3H4) Propin (Metylaxetilen)

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

N u c halogen X2 c d th t t c ankin ph n ng c a ankan: CnH2n 2 + 2X2 CnH2n 2 X4


Ankin Halogen D n xu t tetrahalogen c a ankan

t o d n xu t tetrahalogen

R C

R'

X2
Halogen

R C C X X

R'

Ankin

Dan xuat ihalogen cua anken

X X R C C X X
Dan xuat ihalogen cua anken Halogen

R'

X2

R C C X X

R'

Dan xuat tetrahalogen cua ankan

Neu co X 2 d: R C C
Ankin

X X R' + 2X2 R C C R'


Halogen (dung dch)

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

Propin Me tyl axetilen

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

(Khong ben) HgSO4/H2SO4 , 80 C

Anehit axetic Axetanehit Etanal

CH3

C CH

H2O
Nc

[CH3

C CH2] OH

CH3

C CH3 O

Propin Me tyl axetilen


1 2 3 4

(Khong ben)
+

CH3

Butin-2 imetyl axetilen (1 mol)

C C CH3

H2O
Nc

HgSO4/H2SO4 , 80 C

[CH3

C C OH H

CH3]

Axeton imetyl xeton Propanon

CH3

C CH2 O

CH3

(1 mol)

(Khong ben)

Me tyl etyl xeton Butanon -2

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

Vinyl florua Flo eten

CH2

CH F

HF

, Xt

CH3

CH F

(Qui tac Markovnikov)

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

HgCl2 , 120 - 150 C


0

CH2 CH2

CH Cl CH Cl
n

Hidro clorua

Etyl clorua TH (t , Xt)

nCH2

CH Cl

Vinyl clorua

Polivinyl clorua PVC

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

Este cua ru khong ben

R C

CH

HCN

R C CN

CH2

Axetilen

Axit Xianhiric

Hp chat nitrin khong no

Th d :

Gio khoa ha h u c

Bin so n: V H ng Thi

CH CH

CH3

CH2

OH

HgSO4 (BF3, CCl3-COOH , HgO)

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

CH2 CH CN Acrilonitrin Nitrin acrilic

V.4.7. Ph n ng trng h p a. Ph n ng nh h p axetilen, t o vinyl axetilen


CH CH
+

CH CH

Nh hp (CuCl, NH4Cl, 100 C )


0 Cu+ , 100 C 0

CH2

CH C CH (C4H4)
Vinyl axetilen

Axetilen

(2C2H2)

Axetilen

b. Tam h p axetilen, t o benzen

3CH CH
(3C2H2) Axetilen

Tam hp Than hoat tnh , C , 6000 C

C6H6
Be nze n

c.

a h p axetilen, thu c cupren

Gio khoa ha h u c

Bin so n: V H ng Thi

n CH CH
Axetilen

Trung hp (t 0, Xt) n Polime cua axetilen Cupren

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

t 0, Xt (H2SO 4am ac)


5

CH3
1

( 3 C3H4) Propin Metyl axetilen

H3C

CH3
(C9H12)

1, 3, 5 -Trimetyl benzen Me sitilen

V.4.8. Ph n ng ankin b oxi ha b i dung d ch kali pemanganat (KMnO4 , Thu c tm)

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 )

+ 8KMnO4 3KOOC-COOK + 8MnO2 + 2KOH + 2H2O


Kali pemanganat (Ch t oxi ha) Kali oxalat Mangan ioxit Kali hi roxit

CHCH + 2KMnO4
Axetilen Kali pemanganat (Ch t kh ) (Ch t oxi ha)

+ 3H2SO4 2CO2 + 2MnSO4 + K2SO4 + 4H2O


Axit sunfuric Kh cacbonic Mangan (II) sunfat

Gio khoa ha h u c

10

Bin so n: V H ng Thi

0 1

+7

+3

+4

+2

5CH3-CCH + 8KMnO4 + 12H2SO4 5CH3-COOH + 5CO2 + 8MnSO4 + 4K2SO4 + 12H2O


Propin (Ch t kh )
0 0

Kali pemanganat (Ch t oxi ha)


+7

Axit axetic

+3

+3

5CH3-CC-CH2-CH3 + 6KMnO4 + 9H2SO4 5CH3-COOH + 5CH3-CH2-COOH


Pentin-2 (Ch t kh ) Kali pemanganat (Ch t oxi ha) Axit axetic
+2

Axit propionic

+ 6MnSO4 + 3K2SO4 + 4H2O


V.4.9. Ankin u m ch (Ankin th t, Ankin c n i ba u m ch, R-CCH) tc d ng v i dung d ch b c nitrat trong amoniac, v i dung d ch ng (I) clorua trong amoniac Nguyn t H lin k t v i cacbon mang n i ba u m ch tng i linh ng. [Do H c m i n 2,10 cn C n i n (Csp3) c m i n 2,50; C n i i (Csp2) c m i n 2,69; C n i ba (Csp) c m i n l n nh t, 2,75, nn H lin k t vo C n i ba linh ng hn so v i H lin k t vo C n i n, n i i]. Do nguyn t H linh ng ny d c th b i ion b c (Ag+) c trong dung d ch b c nitrat trong amoniac (AgNO3/NH3), t o s n ph m th l mu i b c khng tan c mu vng nh t, m t lc sau chuy n sang mu xm. Nguyn t H linh ng ny cng d c th b i ion ng (I) (Cu+) c trong dung d ch ng (I) clorua trong amoniac (CuCl/NH3) t o s n ph m th l mu i ng (I) khng tan c mu g ch.

R-CCH
Ankin u m ch Ankylaxetilen

+ AgNO3 + NH3
dd B c nitrat trong amoniac

R-CCAg

NH4NO3

Mu i b c c a ankin u m ch Amoni nitrat B c ankylaxetilua (Ch t khng tan, c mu vng nh t)

R-CCH
Ankin u m ch Ankyl axetilen

CuCl

NH3

R-CCCu

NH4Cl

Dung d ch

ng (I) clorua trong amoniac

Mu i ng (I) c a ankin u m ch ng (I) ankylaxetilua (Ch t khng tan, c mu g ch)

Th d : HCCH + 2AgNO3 + 2NH3


Axetilen Etin

AgCCAg

+ 2NH4NO3

B c axetilua Mu i b c c a etin (Ch t khng tan, c mu vng nh t)

HCCH +
Axetilen Etin dd

2CuCl

+ 2NH3

CuCCCu

+ 2NH4Cl

ng (I) clorua trong amoniac

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

B c metyl axetilen (Ch t khng tan, c mu vng nh t)

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

ng (I) clorua trong amoniac

ng (I) c a butin 1 ng (I) axetilua (Ch t khng tan, c mu g ch)

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

CH3-CC-CH2-CH3 + CuCl + NH3


Pent-2-in; Etylmetylaxetilen

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-CCH + AgNO3 + NH3


Ankin u m ch

R-CCAg R-CCH
Ankin u m ch

NH4NO3

Mu i b c c a ankin u m ch (Ch t khng tan, c mu vng nh t)

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

Dung d ch b c nitrat trong amoniac

AgCCAg

+ 2HCl
Axit clohi ric

HCCH
Axetilen

+ 2AgCl
B c clorua

CH3

CH C CH + AgNO3 + NH3

CH3

CH C CAg

+ NH4NO3

CH3 3-Metylbut-1-in Isopropylaxetilen CH3 CH C CAg CH3 Axit clohiric + HCl

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

(1) (2) (3)

HCCH + Ag2O
Axetilen B c oxit

NH 3 AgCCAg + H2O
B c axetilua N c

HCCH + 2[Ag(NH3)2]+ AgNO3 / 3 AgCCAg + 2NH4+ + 2NH3 NH


Ion ph c c a b c v i amoniac Ion amoni Amoniac

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

CH3-CCH CH3-CCH CH3-CCH

+ AgNO3 + NH3 CH3-CCAg + NH4NO3


B c metylaxetilua

(1) (2) (3)

Propin; Mety axetilen

Ag2O

AgNO3 / 3 2CH3-CCAg + H2O NH

+ [Ag(NH3)2]+ AgNO3 / 3 CH3-CCAg + NH4+ + NH3 NH

CH3-CCH + [Ag(NH3)2]NO3 AgNO3 / 3 CH3-CCAg + NH4NO3 + NH3 (4) NH


AgNO3 / NH CH3-CCH + [Ag(NH3)2]OH 3 CH3-CCAg + 2NH3 + H2O

(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

Vinyl clorua TH (t 0, Xt)

n CH2

CH Cl

CH2

CH Cl n

Vinyl clorua

Polivinyl clorua PVC

Gio khoa ha h u c

14

Bin so n: V H ng Thi

V.5.2.

Axetilen

Cc lo i cao su nhn t o (Buna, Buna-N, Buna-S, Cloropren, Isopren)


, tXt CH2=CH-CCH
0

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

nCH2 CH CH CH2 + nCH CH2 Buta-1,3-ien CN Nitrinacrilic Acrilonitrin

CH2

CH CH CH2 Cao su buna-N

CH CH2 CN n

nCH2

CH CH CH2 + nCH CH2

TH Na

CH2

CH CH CH2

CH CH2 n

Buta-1,3-ien CH2 CH C CH

Stiren; Vinylbenzen + HCl Xt, t o


4 3 2

Cao su buna-S
1

CH2

CH C CH2 Cl

Vinylaxetilen nCH2 CH C CH2 Cl Cloropren

Hiro clorua TH Na

Cloropren; 2-Clobuta-1,3-ien CH2 CH C CH2 Cl Cao su cloropren n

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

Axeton imetyl xeton Propanon

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

H2SO 4(), 180 0C

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

Pd / PbCO3 , t Pd / PbCO3 , t Pd / BaSO4 , t


o o

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.5.5. Propin Mesitilen


CH3 3 CH3 C CH (3 C3H4)
Propin Metyl axetilen Tam h p (t 0, Xt)

(C9H12) H3C CH3


Mesitilen 1,3,5-Trimetyl benzen

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

Oxi (Kho n g kh)


+

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

Oxi (Kho ng kh) C 600 0 C

Nit oxit 600 - 800 0C

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

Clobenzen Phenyl 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

V.5.7. Axetilen Axit axetic o CHCH + H2O HgSO4 80 C


Axetilen N c

CH3-CHO
An ehit axetic

CH3-CHO
An ehit axetic

1 O2 2

Mn

2+

CH3-COOH
Axit axetic

Oxi (Khng kh)

V.5.8. Axetilen CHCH


Axetilen

Nitrin acrilic 0 , Xt + HCN t


Axit xianhi ric

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

Oxi (Khng kh)


0

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

Polivinylaxetat (PV Ac)

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.

i u ch ankin (Ch y u l i u ch axetilen) vi, than Axetilen


V oi song Than coc
t 0 cao
0 (1000 C)

V.6.1. T
a voi Than a CaCO 3

Canxi cacbua (a t en, Kh a)

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)

Than coc (C)


0

3C
Than co c

Lo ie n (Ho quang, 2000 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

V.6.2. Metan Axetilen Hi n nay ng i ta i u ch axetilen theo phng php ny.


2 CH4
Metan 1500 C La m la nh nhanh
0

C2H2
Axetilen

3 H2

Hiro

V.6.3. D n xu t , - tetrahalogen c a ankan tc d ng v i b t k m (Zn) hay natri (Na) Ankin


X X R C C X X R'
+

2 Zn
Bo t ke m

R C C
Ankin

R'

2 ZnX2
Ke m halogenua

Da n xua t anpha, beta tetra halogen cua ankan

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

Da n xua t anpha, beta halogen cu a ankan R u t0

R CH2 CH X X

2 KOH

R C CH
Ankin

2 KX

2 H2O

Da n xua t anpha, anpha halogen cu a ankan

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

Propin Me tyl axetilen

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

V.6.5. Cho mu i b c c a ankin u m ch

u m ch tc d ng v i axit clohi ric


Ankin

R-CCAg
B c axetilua

HCl

R-CCH
Ankin u m ch

AgCl
B c clorua

Axit clohi ric

Th d : AgCCAg
B c axetilua

+ +

2HCl HCl

HCCH
Axetilen

2AgCl
B c clorua

Axit clohi ric

CH3-CCAg
B c metylaxetilua

CH3-CCH
Propin

AgCl
B c clorua

Axit clohi ric

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.

3. Vi t cng th c c u t o thu g n cc ch t c tn sau y:

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

H2SO4() , 180 C (4)

A4

dd KMnO4 (5)

H2SO4() , 180 C (6)

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

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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

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trong NH3 th th y t o ra ch t khng tan c mu vng nh t. C bao mhiu cng th c c u t o ph h p c a A? A. 1 B. 2 C. 3 D. 4


20. D n 4,48 lt h n h p g m hai kh axetilen v etilen qua l ng d dung d ch b c nitrat trong amoniac, c 3,36 lt kh thot ra v c m gam k t t a. Th tch kh o i u ki n tiu chu n. Tr s c a m l: A. 12 B. 6 C. 16 D. 24 (C = 12; H = 1; Ag = 108) 21. V i cc ch t: butan, buta ien, propilen, but-2-in, axetilen, metylaxetilen, isobutan, isobutilen, anlen. Ch n pht bi u ng v cc ch t trn: A. C 3 ch t tc d ng dung d ch AgNO3/NH3 t o k t t a mu vng nh t B. C 6 ch t lm m t mu n c brom C. C 7 ch t lm m t mu tm c a dung d ch KMnO4 D. C 3 ch t khng tham gia ph n ng c ng hi ro 22. T metan, ng i ta c th i u ch cao su buna theo s sau: HS 80% HS 70% HS 60% HS 90% Metan Axetilen Vinylaxetilen Buta-1,3- ien Cao su buna

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

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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)

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