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

V.1. nh ngha Ankin l mt loi hirocacbon m trong phn t c cha mt lin kt ba, mch h. V.2. Cng thc tng qut CnH2n 2 (n 2)

V.3. Cch c tn (Danh php) - Ankan Ankin (C thm s ch v tr ca lin kt ba, t gia hoc pha sau
hoc pha trc, c nh s nh. Mch chnh l mch cacbon c cha lin kt ba CC, di nht v mang nhiu nhm th hn)

Th d:

c tn cc gc hirocacbon lin kt vo cacbon mang ni ba, ri thm ch axetilen (Coi cc gc hirocacbon lin kt vo cacbon mang ni ba nh l cc nhm th th H ca 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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V.4. Tnh cht ha hc V.4.1. Phn ng chy t0 CnH2n 2 + (3n 1)/2 O2 nCO2 + (n 1)H2O 1 mol n mol (n 1) mol Ankin chy to s mol H2O < s mol CO2 hay th tch hi nc nh hn so vi kh cacbonic (o trong cng iu kin v nhit v p sut) V.4.2. Phn ng cng hiro (Phn ng hiro-ha) ankin cng hiro (H2) phi cn dng cht xc tc thch hp [Ni (Niken, Nickel) hay Pt (Bch kim, Platin)] v un nng. Ankin cng H2 to anken, ri ankan. CnH2n 2 + H2
Ankin Hiro
Pt ) , t Ni ( Pt ) , t Ni (
0 0

CnH2n
Anken (Olefin)

CnH2n
Anken

+ H2
Hiro

CnH2n + 2
Ankan (Parafin)

Khi c H2 d hay va v phn ng hon ton (hay hiu sut 100%) th ankin mi phn ng ht to ankan. CnH2n 2
Ankin (1 mol)

+ 2H2
Hiro (2 mol)

Pt ) , t Ni (

CnH2n + 2
Ankan

R-CC-R + H2
Ankin Anken Hiro

Pt ) , t Ni (

R-CH=CH-R
Anken

R-CH=CH-R +

H2

Ni ( Pt ) , t 0

R-CH2-CH2-R
Ankan

Khi c H2 d (hay va ) v phn ng hon ton (phn ng hiu sut 100%, phn ng kt thc, phn ng xong), th: R-CC-R + 2H2
Ankin Hiro
Pt ) , t Ni ( Pt ) , t Ni (
0 0

Pt ) , t Ni (

R-CH2-CH2-R
Ankan (Parafin)

Th d: CHCH + H2
Axetilen (Etin) Hiro

CH2=CH2
Etilen (Eten)

CH2=CH2
Etilen

+ H2

CH3-CH3
Etan

Nu c H2 d (hay va ) v phn ng hon ton th axetilen phn ng ht v to ra etan: Pt ) , t 0 CHCH + 2H2 Ni ( CH3-CH3
(C2H2) Axetilen Hiro (C2H6) Etan

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Pt ) , t CH3-CCH + H2 Ni ( CH3-CH=CH2 (Propen; Propilen) Ni ( Pt ) , t 0 CH3-CH=CH2 + H2 CH3-CH2-CH3 (Propan)

Nu phn ng hon ton v c H2 d hay va th propin phn ng ht to propan. CH3-CCH + 2H2

Hiro
Pt ) , t Ni ( CH3-CH2-CH3
0

(C3H4) Propin (Metylaxetilen)

(C3H8) Propan

Lu L.1. Phn ng cng hiro (H2) vo ankin thng xy ra khng hon ton. Sau phn ng, c th thu c ankan, anken ln ankin v H2. Ch khi no gi thit cho c H2 d hay va v phn ng hon ton (hiu sut 100%, phn ng xong, phn ng kt thc), th tt c lng ankin c lc u mi phn ng ht to ankan. L.2. Mun phn ng ankin cng H2 to ra ch yu l anken th ta dng H2 khng d v dng cht xc tc Pd/PbCO3 (cht xc tc palai, paladium, trn cht mang ch cacbonat, hay palai trn cht mang BaSO4), un nng. R-CC-R + H2
Ankin (1 mol) Hiro (1 mol)
/ PbCO 3 , t Pd
0

R-CH=CH-R
Anken (Olefin)

Th d: CHCH + H2
(C2H2) Axetilen Hiro
/ PbCO 3 , t Pd
0

CH2=CH2
(C2H4) Etilen

Bi tp 35 Hn hp kh A gm axetilen v hiro c th tch 3,52 lt ( 27,3C; 106,4 cmHg) c cho vo mt bnh kn c cha mt t bt Ni lm xc tc. un nng bnh mt thi gian, thu c hn hp kh B. a. Hn hp B c th gm cc cht no? b. T khi ca hn hp A so vi heli bng 2. Tnh khi lng hn hp B. c. Trong hn hp B trn c cha 0,01 mol mt cht m khi t chy to s mol nc nh hn s mol CO2; 0,9 gam mt cht m khi t chy to s mol nc ln hn CO2. Tnh phn trm th tch mi kh trong hn hp B v hiu sut phn ng axetilen cng hiro. (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 tp 35 Hn hp kh X gm metyl axetilen v hiro. Cho 2,464 lt hn hp X (o 27,3C; 1,4 atm) vo mt bnh kn c cha mt t bt Niken lm xc tc. un nng bnh mt thi gian, thu c hn hp kh Y. a. Hn hp Y c th gm cc cht no?

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b. T khi hi ca hn hp X so vi hiro bng

109 . Xc nh khi lng hn hp 14

Y. c. Trong hn hp Y trn c cha 672 mL (ktc) mt kh m khi t chy khng to CO2; 0,84 gam mt kh m khi t chy to s mol nc bng s mol CO2. Tnh phn trm khi lng mi kh trong hn hp Y. Tnh hiu sut phn ng H2 cng hirocacbon 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 cng halogen X2 (Cl2, Br2, I2) CnH2n 2
Ankin

X2
Halogen

CnH2n 2X2
Dn xut iahalogen ca anken

CnH2n 2X2

X2

CnH2n 2 X4
Dn xut tetrahalogen ca ankan

Dn xut ihalogen ca anken

Nu c halogen X2 c d th tt c ankin phn ng to dn xut tetrahalogen ca ankan: CnH2n 2 + 2X2 CnH2n 2 X4

Ankin Halogen Dn xut tetrahalogen ca ankan

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 dng vi halogen X2, halogen cng vo ankin to dn xut ihalogen ca anken, ri halogen cng tip vo dn xut ihalogen ca anken to ra dn xut tetrahalogen ca ankan. Ankin cng halogen d dng, ch cn dng dung dch halogen v phn ng xy ra c ngay c trong bng ti. V phn ng xy ra d, nn nu c d halogen X2, th tt c ankin phn ng ht to dn xut tetrahalogen ca ankan; V ngc li, nu c d hirocacbon khng no th halogen phn ng ht. Tuy nhin, nu halogen X2 thiu th sau phn ng c th thu c ankin cn d; sn phm cng dn xut

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ihalogen ca anken, dn xut tetrahahlogen ca ankan (sn phm cng ni i ln ni n). Mun phn ng ankin cng brom dng giai on to dn xut ibrom ca anken th thc hin
nhit thp (-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 Nu cho axetilen phn ng trc tip vi kh clo (Cl2) nguyn cht th s c hin tng n, do c phn ng: C2H2 + Cl2 2C + 2HCl Do c phn ng cng clo vo axetilen, ngi ta dng dung dch clo. Bi tp 36 Dn 1,008 lt axetilen (ktc) qua 200 mL dung dch Br2 0,25 M. Dung dch brom b mt mu hon ton v c 336 mL mt kh (ktc) thot ra. Tnh khi lng cc sn phm cng brom thu c. Cc phn ng xy ra hon ton. (C = 12 ; H = 1 ; Br = 80) S: 1,86 gam CHBr=CHBr; 6,92 gam CHBr2-CHBr2 Bi tp 36 Cho 672 mL metylaxetilen (ktc) qua 1,75 lt dung dch nc brom c nng 0,02 mol/lt. Nc brom mt mu hon ton v c 308 mL mt kh thot ra ( 27,3C; 608 mmHg). Tnh khi lng sn phm cng brom thu c.

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Cho bit cc sn phm cng brom tan trong dung dch. Cc phn ng xy 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 cng nc (hp nc, Hirat ha ankin) Ankin cng nc theo t l mol 1 : 1, c mui thy ngn (II) sunfat (HgSO4), trong mi trng axit sunfuric, un nng 80C, th ch c ankin n gin nht l axetilen mi to c anehit, l anehit axetic (CH3-CHO). Cc ankin khc cng nc vi iu kin nh trn ch to xeton (ceton, R-CO-R). Phn ng cng HX, cng H2O vo ankin cng theo qui tc Markovnikov ging nh cng 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 cng HX (Hiro halogenua) Ankin cng hiro halogenua (HX) kh hn cng halogen (X2). Tc dng ca hiro florua (HF) vo axetilen lc u to vinyl florua, sau to 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 thut tng hp nha polivinyl clorua (PVC), mun iu ch vinyl clorua, ngi ta cho axetilen tc dng vi hiro clorua (HCl) trn xc tc thy ngn (II) clorua (HgCl2) 120 150C. Nu khng c xc tc HgCl2, th c phn ng tip gia vinyl clorua vi HCl to thnh 1,1-iclo etan (CH3-CHCl2)

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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 cng ru (R-OH), cng axit hu c (R-COOH), axit xianhiric (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:

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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. Phn ng trng hp a. Phn ng nh hp axetilen, to 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 hp axetilen, to benzen

3CH CH
(3C2H2) Axetilen

Tam hp Than hoat tnh , C , 6000 C

C6H6
Be nze n

c. a hp axetilen, thu c cupren

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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 mt bt ng (Cu) v vt oxi 200-250C, axetilen trng hp to thnh mt polime, l cupren. y l mt cht bt v nh hnh, khi lng phn t rt ln, khng tan trong nc v cc dung mi hu c. Cupren c dng lm cht cch in, cch nhit.
d. Tam hp propin, thu c cht 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. Phn ng ankin b oxi ha bi dung dch kali pemanganat (KMnO4 , Thuc tm)

R-CC-R + 3[O]
Ankin

+ H2O
4 dd KMnO

4 dd KMnO

R-COOH +
Axit hu c

R-COOH
Axit hu c

CHCH + 4[O]
Axetilen

HOOC-COOH
Axit oxalic; Axit etanioic

3CHCH
Axetilen (Cht kh)

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

Kali pemanganat (Cht oxi ha) Kali oxalat Mangan ioxit Kali hiroxit

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

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

Axit sunfuric Kh cacbonic Mangan (II) sunfat

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0 1

+7

+3

+4

+2

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

Propin (Cht kh)
0 0

Kali pemanganat (Cht oxi ha)

+7

Axit axetic

+3

+3

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

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

Axit propionic

+ 6MnSO4 + 3K2SO4 + 4H2O

V.4.9. Ankin u mch (Ankin tht, Ankin c ni ba u mch, R-CCH) tc dng vi dung dch bc nitrat trong amoniac, vi dung dch ng (I) clorua trong amoniac Nguyn t H lin kt vi cacbon mang ni ba u mch tng i linh ng. [Do H c m in 2,10 cn C ni n (Csp3) c m in 2,50; C ni i (Csp2) c m in 2,69; C ni ba (Csp) c m in ln nht, 2,75, nn H lin kt vo C ni ba linh ng hn so vi H lin kt vo C ni n, ni i]. Do nguyn t H linh ng ny d c th bi ion bc (Ag+) c trong dung dch bc nitrat trong amoniac (AgNO3/NH3), to sn phm th l mui bc khng tan c mu vng nht, mt lc sau chuyn sang mu xm. Nguyn t H linh ng ny cng d c th bi ion ng (I) (Cu+) c trong dung dch ng (I) clorua trong amoniac (CuCl/NH3) to sn phm th l mui ng (I) khng tan c mu gch.

R-CCH
Ankin u mch Ankylaxetilen

+ AgNO3 + NH3
dd Bc nitrat trong amoniac

R-CCAg

NH4NO3

Mui bc ca ankin u mch Amoni nitrat Bc ankylaxetilua (Cht khng tan, c mu vng nht)

R-CCH
Ankin u mch Ankyl axetilen

CuCl

NH3

R-CCCu

NH4Cl

Dung dch ng (I) clorua trong amoniac

Mui ng (I) ca ankin u mch ng (I) ankylaxetilua (Cht khng tan, c mu gch)

Th d: HCCH + 2AgNO3 + 2NH3

Axetilen Etin

AgCCAg

+ 2NH4NO3

Bc axetilua Mui bc ca etin (Cht khng tan, c mu vng nht)

HCCH +
Axetilen Etin

2CuCl

+ 2NH3

CuCCCu

+ 2NH4Cl

dd ng (I) clorua trong amoniac

ng (I) axetilua Amoni clorua Mui ng (I) ca etin (Cht khng tan, c mu gch)

2CH3-CCH
Propin, Metylaxetilen

+ AgNO3 + NH3

2CH3-CCAg

+ NH4NO3

Bc metyl axetilen (Cht khng tan, c mu vng nht)

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CH3-CH2-CCH
Butin 1 Etyl axetilen

CuCl + NH3

CH3-CH2-CCCu

+ NH4Cl

dd ng (I) clorua trong amoniac

Mui ng (I) ca butin 1 ng (I) axetilua (Cht khng tan, c mu gch)

Lu L.1. Chng trnh ph thng hin nay khng hc phn ng gia ankin u mch vi dung dch ng (I) clorua trong amoniac. L.2. Ankin cha ni ba trong mch (R-CC-R) khng tc dng vi dung dch AgNO3/NH3 cng nh dung dch 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. Ngi ta thng dng phn ng c trng ny nhn bit ankin u mch, cng nh tch ly ankin u mch ra khi hn hp cch cht hu c. Nu l ankin u mch th khi cho tc dng vi dung dch bc nitrat trong amoniac (AgNO3/NH3) s thu c cht khng tan c mu vng nht. Cho hn hp cc cht hu c c cha ankin u mch tc dng vi dung dch bc nitrat trong amoniac th ch c ankin u mch phn ng to cht khng tan c mu vng nht. Sau lc ly cht khng tan ny cho tc dng vi dung dch axit clohiric (HCl) s ti to c ankin u mch.

R-CCH + AgNO3 + NH3

Ankin u mch

R-CCAg R-CCH
Ankin u mch

NH4NO3

Mui bc ca ankin u mch (Cht khng tan, c mu vng nht)

R-CCAg Th d: HCCH
Axetilen

HCl
Axit clohiric

+ AgCl
Bc clorua

Mui bc ca ankin u mch

2AgNO3

+ 2NH3

AgCCAg
Bc axetilua

+ 2NH4NO3

Dung dch bc nitrat trong amoniac

AgCCAg

+ 2HCl
Axit clohiric

HCCH
Axetilen

+ 2AgCl
Bc 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

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Bi tp 37 Tch ly ring tng kh ra khi hn hp gm: metan, etilen v axetilen. Bi tp 37 Hy tch ly ring tng cht ra khi hn hp gm cc kh sau y: Propan, propilen v propin. L.4. Thc ra khi cho mui bc nitrat vo dung dch amoniac th c s to phc cht c cha ion phc l [Ag(NH3)2]+ tan trong dung dch. Cng nh khi cho ng (I) clorua vo dung dch amoniac l c s to ion phc [Ag(NH3)2]+ tan. Trong sch ph thng c vit Ag2O nhm n gin ha. Do vy phn ng gia ankin u mch vi dung dch bc nitrat c cc cch vit khc nhau nh sau:

R-CCH + AgNO3 + NH3 R-CCAg + NH4NO3

3 / NH 3 R-CCH + Ag2O AgNO R-CCAg + H2O

3 / NH 3 R-CCH + [Ag(NH3)2]+ AgNO R-CCAg + NH4+ + NH3

3 / NH 3 R-CCH + [Ag(NH3)2]NO3 AgNO R-CCAg + NH4NO3 + NH3

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

Sch ph thng (khng nng cao, chng trnh chun) hin nay vit theo cch u, ngha l c sao vit vy. Cn sch nng cao vit phn ng ny theo cch cui, dng phc [Ag(NH3)2]OH.

Th d: Vit phn ng gia axetilen vi dung dch bc nitrat trong amoniac theo 5 cch. HCCH + 2AgNO3 + 2NH3 AgCCAg + 2NH4NO3
dd Bc nitrat trong amoniac Amoni nitrat

(1) (2) (3)

HCCH + Ag2O
Axetilen Bc oxit

3 NH AgCCAg + H2O

Bc axetilua

Nc

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

Ion phc ca bc vi amoniac

Ion amoni

Amoniac

3 / NH 3 HCCH + 2[Ag(NH3)2]NO3 AgNO AgCCAg + 2NH4NO3 + 2NH3 (4)

3 / NH 3 HCCH + 2[Ag(NH3)2]OH AgNO AgCCAg + 4NH3 + 2H2O

(5)

Th d khc: Vit phn ng gia propin vi dung dch bc nitrat trong amoniac theo 5 cch.

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Bin son: V Hng Thi

CH3-CCH CH3-CCH CH3-CCH

+ AgNO3 + NH3 CH3-CCAg + NH4NO3

Bc metylaxetilua

(1) (2) (3)

Propin; Mety axetilen

Ag2O

3 / NH 3 AgNO 2CH3-CCAg + H2O

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

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

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

(5)

Th d t lm: Vit phn ng gia isopropyl axetilen vi dung dch bc nitrat trong amoniac theo cc cch khc nhau.
L.5. thi tuyn sinh i hc hin nay do B Gio Dc v o To ra chung cho c nc, theo st chng trnh sch gio khoa ph thng. Do o chng ta nn theo cch vit ph thng khi lm bi. Nh vy trong 5 cch trn, nu hc theo chng trnh chun (khng nng cao), th chng ta vit theo cch (1). Theo chng trnh nng cao th vit theo cch (5). Bi tp 38 Cht A c CTPT C10H10. Cho 2,6 gam cht A tc dng hon ton vi lng d dung dch AgNO3/NH3, thu c 9,02 gam mt cht khng tan c mu vng nht. Xc nh CTCT ca A. Bit rng khi hiro ha hon ton A th thu c cht 4-etyl-3metylheptan. (C = 12 ; H = 1 ; Ag = 108) Bi tp 38 X l mt hirocacbon c CTPT C12H16. em 2,4 gam cht X tc dng vi lng d dung dch bc trong amoniac, phn ng xong, thu c 5,61 gam mt cht khng tan c mu vng nht. Nu em kh hon ton cht X bng H2 th thu c cht 1-etyl-4-butyl xiclohexan. Xc nh CTCT ca X. Vit cc phng trnh phn ng xy ra. (C = 12 ; H = 1 ; Ag = 108) V.5. ng dng 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

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Bin son: V Hng Thi

V.5.2.

Axetilen

Cc loi cao su nhn to (Buna, Buna-N, Buna-S, Cloropren, Isopren)

, Xt t CH2=CH-CCH
0

CHCH + HCCH
Axetilen Axetilen

Vinylaxetilen
0

, t CH2=CH-CCH + H2 Pd CH2=CH-CH=CH2

Vinyl axetilen

Hiro

Buta-1,3-ien

Na n CH2=CH-CH=CH2 TH (-CH2-CH=CH-CH2-)n

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 Ru 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 hp (t , Xt)

CH2=CH-CCH
Vinyl axetilen

CH2=CH-CCH + 3H2
Hiro

Ni ,t 0

CH3-CH2-CH2-CH3
Butan; n- Butan

CH3-CH2-CH2-CH3
n-Butan

( t , , Xt Cracking

CH4
Metan

+ CH2=CH-CH3
Propen (Propilen)

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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 dng hiro dng cht xc tc l hn hp Pd/PbCO3 hoc Pd/BaSO4, un nng, th ankin ch cng mt phn t hiro to anken tng ng.

R-CC-R +
Ankin

H2
Hiro

/ PbCO 3 , t Pd

R-CH=CH-R
Anken (Olefin)

Th d: CHCH + H2
Axetilen Hiro
/ BaSO 4 , t Pd
o

/ PbCO 3 , t Pd

CH2=CH2
Etilen

CH3-CCH + H2
Propin Hiro

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)

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Bin son: V Hng 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 Nha phenolfomanehit Axetilen Anehit axetic Axit axetic Natri axetat Metan Fomanehit Axetilen Benzen Clobenzen Phenol Nha phenolfomanehit
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

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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 4 80 C CHCH + H2O HgSO

Axetilen Nc

CH3-CHO
Anehit axetic

CH3-CHO
Anehit 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 xianhiric

CH2=CH-CN
Nitrin acrilic; Acrilonitrin; Acrilonitril

V.5.9. Axetilen PVAc , PVA Axetilen Anehit axetic Axit axetic Vinyl axetat Polivinyl axetat (PVAc) Polivinyl ancol (PVA)

CHCH + H2O
Axetilen Nc

4 80 C HgSO

CH3-CHO
Anehit axetic

CH3-CHO
Anehit axetic

1 O2 2

Mn

2+

CH3-COOH
Axit axetic

Oxi (Khng kh)

0

CH3-COOH + CHCH
Axit axetic Axetilen

, Xt ( Zn ( CH 3COO ) 2 ) t

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 thp sng (n kh ); bm bong bng bay;

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V.6. iu ch ankin (Ch yu l iu ch axetilen) V.6.1. T vi, than Axetilen

a voi Than a CaCO 3 V oi song Than coc
t 0 cao
0 (1000 C)

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 Hin nay ngi ta iu 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. Dn xut , - tetrahalogen ca ankan tc dng vi bt km (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

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Bin son: V Hng Thi

Ngi ta thng dng phng php iu ch ny tch ly ankin (ch yu l ankin gia mch) ra khi hn hp cc cht hu c. Cho hn hp cc cht hu c, c cha ankin, tc dng vi nc brom d. Ankin phn ng to sn phm cng brom b gi li trong dung dch. Sau cho bt km vo sn phm cng brom, s ti to c ankin.
Bi tp 39 imetyl axetilen c ln metan v propan. Hy tinh ch imetyl axetilen. Bi tp 39 Hy tch ly ring tng kh ra khi hn hp gm cc kh sau y: Butan, But-2-in v Cacbon ioxit. V.6.4. Dn xut , -ihalogen hay , -ihalogen ca ankan tc dng vi KOH trong ru (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 Ngi ta thng vn dng phng php iu ch ny chuyn ha mt anken thnh ankin tng ng. Cho anken tc dng vi nc brom (dung dch brom), anken phn ng to sn phm cng brom. Sau cho sn phm cng brom ny tc dng vi KOH trong ru, un nng, s thu c ankin tng ng. Bi tp 40 Vit phng trnh phn ng chuyn ha qua li gia etilen vi axetilen. Bi tp 40 Vit phng trnh phn ng iu ch qua li gia propen vi propin.

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Bin son: V Hng Thi

V.6.5. Cho mui bc ca ankin u mch tc dng vi axit clohiric u mch

Ankin

R-CCAg
Bc axetilua

HCl

R-CCH
Ankin u mch

AgCl
Bc clorua

Axit clohiric

Th d: AgCCAg
Bc axetilua

+ +

2HCl HCl

HCCH
Axetilen

2AgCl
Bc clorua

Axit clohiric

CH3-CCAg
Bc metylaxetilua

CH3-CCH
Propin

AgCl
Bc clorua

Axit clohiric

Lu Ngi ta thng dng phng php iu ch ny tch ly ring ankin u mch ra khi hn hp cc cht hu c. Cho hn hp cc cht hu c, c cha ankin u mch, tc dng vi dung dch bc nitrat trong amoniac. Ankin u mch phn ng, to mui bc ca ankin u mch. Mui ny khng tan, c mu vng nht. Lc ly cht khng tan ny cho tc dng vi dung dch axit clohiric, s ti to c ankin u mch. Bi tp 41 Hn hp kh A gm metan, etilen v axetilen. Hy dng phng php ha hc tch ly ring mi cht ra khi hn hp A. Bi tp 41 Hn hp X gm cc kh: etan, propin v imetylaxetilen. Hy tch ly ring mi kh ra khi hn hp X. Bi tp 42 Hn hp A gm hai ankin hn km nhau mt nhm metylen trong phn t. Cho 6,6 gam hn hp A hp th vo lng d dung dch bc nitrat trong amoniac, thu c 38,7 gam cht rn khng tan, c mu vng nht. Khng cn hirocacbon sau phn ng. a. Xc nh cng thc hai ankin trn. b. Tnh phn trm khi lng mi cht trong hn hp A. c. Nu un nng hn hp A trong bnh kn vi cht xc tc thch hp, thu c hai hirocacbon tng ng, c cu to cn xng. Xc nh hai hirocacbon ny v c tn chng. Hy cho bit cc sn phm 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 tp 42 Hn hp A gm hai ankin u mch lin tip (khng c axetilen). Cho 3,22 gam hn hp A tc dng hon ton vi lng d dung dch AgNO3/NH3, thu c 10,71 gam cht rn mu vng. a. Xc nh CTPT, CTCT v tn ca hai ankin trn.

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b. Tnh khi lng mi cht trong 3,22 gam hn hp A. c. Trng hp ankin c khi lng phn t nh trong hn hp A, thu c mt hirocacbon thm B. Vit phng trnh phn ng to B v phn ng gia B vi dung dch KMnO4, bit rng c to mui ca axit a chc thm, ng thi c to cht rn mu en. (C = 12 ; H = 1 ; Ag = 108) S: 1,6 gam CH3-CCH ; 1,62 gam CH3-CH2-CCH

CU HI N PHN V
1. Ankin l g? Hy cho bit cng thc tng qut ca ankin. 2. c tn cc cht sau y:
a. CH3 C C CH CH3 CH3 c. CH3 CH3 CH3 CH CH C CH CH C CH d. CH2 CH CH2 C CH b. CH3 CH3 CH2 CH2 C CH2 CH CH3 C CH CH3

3. Vit cng thc cu to thu gn cc cht 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 mt cht hu c thuc dy ng ng ankin. t chy 0,5 mol A, thu c 2 mol CO2. A tc dng c dung dch bc nitrat trong amoniac. Xc nh CTCT v c tn A. Vit cc phng trnh phn ng xy ra. S: But-1-in 5. X l mt hirocacbon. Mt th tch hi X vi 4,875 th tch kh metan c cng khi lng (cc th tch kh, hi o trong cng iu kin v nhit v p sut). Cho 7,8 gam X tc dng ht vi dung dch bc nitrat trong amoniac, thu c 29,2 gam cht rn khng tan, c mu vng. Xc nh CTCT ca X. Bit rng X c cu to mch h, phn nhnh. (C = 12 ; H = 1 ; Ag = 108) 6. t chy hon ton 4 gam cht hu c A. Sn phm chy ch gm 6,72 lt CO2 (ktc) v 3,6 gam H2O. T khi hi ca A nh hn 1,5. Xc nh CTCT ca A. Vit phng trnh phn ng ca A vi: H2 (c Ni lm xc tc, un nng); Nc brom (d); Nc brom (thiu); Dung dch KMnO4 (trong mi trng axit H2SO4); Dung dch KMnO4 (trong mi trng trung tnh H2O); H2O (t mol 1 : 1, c mui

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Hg2+ lm xc tc, 80C); HCN (t l 1 : 1, c cht xc tc, nhit thch hp); Phn ng tam hp A; Phn ng trng hp (a hp) A; Phn ng chy ca A; Dung dch AgNO3/NH3. Cho bit A tc dng c dung dch bc nitrat trong amoniac. (C = 12 ; H = 1 ; O = 16)
7. Hn hp A gm hai ankin c khi lng phn t hn km nhau 14 vC. Cho bit 3,82 gam hn hp A lm mt mu va dung dch brom c ha tan 16 gam brom. Sn phm thu c ch gm lin kt n. a. Xc nh CTPT ca hai hirocacbon trong hn hp A. b. Tnh % s phn t gam mi cht trong hn hp A. c. Xc nh cc CTCT c th c ca hai ankin trn. c tn mi cht. Cho bit hai cht trong hn hp A u c cu to mch thng. (C = 12 ; H = 1 ; Br = 80) S: 40% C5H8; 60% C6H10 8. Vit phng trnh phn ng theo s sau y (mi mi tn l mt phn ng): Metan Axetilen Anehit axetic Axit axetic Natri axetat Metan Fomanehit Ru metylic Anehit fomic Axit fomic Metyl fomiat Natri fomiat Hiro Amoniac Nit oxit Nit ioxit Axit nitric. 9. Hn hp X gm ba kh l metan, etilen v axetilen. Nu t chy ht 3,36 lt hn hp X (ktc) ri cho sn phm chy hp th vo nc vi d th thu c 24 gam kt ta. Cn nu ly 13,6 gam hn hp X cho tc dng vi lng d dung dch bc nitrat trong amoniac th thu c 38,4 gam kt ta. Xc nh % khi lng mi cht trong hn hp X. Cc phn ng xy 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 (cht xc tc c ), hy vit phng trnh phn ng iu ch: Polivinyl axetat v axit picric (2,4,6-trinitrophenol). ( TSH, i hc S Phm v i hc Lut tp HCM, nm 2001) 11. Vit phng trnh phn ng theo s sau:
Cn H 2n+2 A2
Cl2, askt , 1 : 1 (1)
0

A1

(2)

A2 A5

(3)

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. Hn hp Z gm 0,15 mol CH4; 0,09 mol C2H2 v 0,2 mol H2. Nung nng hn hp Z vi xc tc Ni thu hn hp Y. Cho Y qua dung dch brom d thu c hn hp

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Bin son: V Hng Thi

kh A c phn t lng trung bnh l 16. tng khi lng dung dch brom l 0,82 gam. Tnh s mol mi cht trong A. (C = 12 ; H = 1 ; Br = 80) ( TSH, i hc Quc gia tp HCM, nm 2001) S: 0,15 mol CH4; 0,06 mol C2H6; 0,06 mol H2
13. X v Y l hai hirocacbon c cng CTPT l C5H8. X l monome dng trng hp thnh cao su isopren; Y c mch cacbon phn nhnh v to kt ta vi dung dch NH3 c Ag2O. Hy cho bit CTCT ca X v Y. Vit cc phng trnh phn ng xy ra. ( TSH, nm 2002) 14. Cht A c cng thc phn t l C7H8. Cho A tc dng vi Ag2O (d) trong dung dch amoniac c cht B kt ta. Khi lng phn t ca B ln hn ca A l 214 vC. Vit cc CTCT c th c ca A. (Ag = 108 ; H = 1) ( TSH khi B, nm 2003) S: 4 CTCT 15. Cho hn hp A gm 0,3 mol C2H2 v 0,6 mol H2 i qua ng s cha Ni, un nng. Thu c hn hp kh B. Dn hn hp B qua bnh ng nc brom c d. Bnh brom tng thm m gam, c 8,96 lt hn hp kh C thot ra (ktc) khi bnh nc brom, trong C khng c hi nc. T khi hn hp C so vi kh heli bng 3,125. Tr s ca m l: a) 2 gam b) 4 gam c) 6 gam d) 5 gam (C = 12; H = 1; He = 4) 16. X l mt hirocabon c CTPT C10H6. Cho 12,6 gam X tc dng hon ton vi lng d dung dch bc nitrat trong amoniac, thu c 34 gam mt cht rn mu vng nht. Phn t X c cha: a) 4 lin kt ba CC u mch b) 3 lin kt ba CC u mch c) 2 lin kt ba CC u mch d) 1 lin kt ba CC u mch (C = 12; H = 1; Ag = 108) 17. Cho 2,912 lt metylaxetilen (ktc) li qua 1,4 lt dung dch Br2 0,1 M. Tt c brom mt mu ht. C 672 mL mt kh (ktc) thot ra khi bnh nc brom. Khi lng sn phm cng brom thu c l: a) 26,4 gam b) 34,4 gam c) 50,4 gam d) Tt c u khng ng (C = 12; H = 1; Br = 80) 18. Hn hp A gm canxi cacbua v natri hirua. Cho 11,2 gam hn hp A tc dng hon ton vi lng nc d, thu c hn hp B gm hai kh. Cho lng hn hp B qua ng s c Ni lm xc tc, un nng, thu c mt cht D duy nht. D khng lm mt mu dung dch KMnO4. Thnh phn phn trm khi lng mi cht trong hn hp 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 mt hirocacbon m 1 mol A cng c 2 mol H2 to ankan tng ng. Khi t chy 1 mol A th thu c 5 mol CO2 v khi cho A tc dng vi dung dch AgNO3

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trong NH3 th thy to ra cht khng tan c mu vng nht. C bao mhiu cng thc cu to ph hp ca A? A. 1 B. 2 C. 3 D. 4
20. Dn 4,48 lt hn hp gm hai kh axetilen v etilen qua lng d dung dch bc nitrat trong amoniac, c 3,36 lt kh thot ra v c m gam kt ta. Th tch kh o iu kin tiu chun. Tr s ca m l: A. 12 B. 6 C. 16 D. 24 (C = 12; H = 1; Ag = 108) 21. Vi cc cht: butan, butaien, propilen, but-2-in, axetilen, metylaxetilen, isobutan, isobutilen, anlen. Chn pht biu ng v cc cht trn: A. C 3 cht tc dng dung dch AgNO3/NH3 to kt ta mu vng nht B. C 6 cht lm mt mu nc brom C. C 7 cht lm mt mu tm ca dung dch KMnO4 D. C 3 cht khng tham gia phn ng cng hiro 22. T metan, ngi ta c th iu ch cao su buna theo s sau: HS 80% 70% 60% 90% Metan Axetilen HS Vinylaxetilen HS Buta-1,3-ien HS Cao su buna

Khi lng cao su thu c theo s trn nu dng 1000 m3 metan (ktc) lc u l: A. 729 kg B. 364,50 kg C. 91,13 kg D. 182,25 kg (C = 12; H = 1)
23. em nung nng mt lng kh metan 1500C ri lm lnh nhanh, thu c hn hp kh A gm axetilen, hiro v metan cha b nhit phn. T khi ca A so vi oxi bng 0,3. Hiu sut phn ng nhit phn metan l: A. 66,67% B. 70% C. 83,33% D. 90% (C = 12; H = 1; O = 16) 24. A l mt ankin. Khi t chy a mol A, thu c 6a mol CO2. A c th c bao nhiu cng thc cu to? A. 5 B. 6 C. 7 D. 8 25. Hn hp kh A gm etan, etilen v axetilen. Dn 13,44 lt hn A qua lng d dung dch brom th c 6,72 lt kh thot ra. Cn nu cho cng lng hn hp A trn qua lng d dung dch AgNO3 trong NH3 th thu c 24 gam kt ta. Phn trm khi lng mi cht trong hn hp 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 mt cht hu c m khi t chy ch to CO2 v H2O. em t chy ht 5,2 gam A, ri dn sn phm chy ln lt qua bnh (1) ng P2O5 d v bnh (2) ng nc vi d. Khi lng bnh (1) tng 3,6 gam. Trong bnh (2) c 40 gam kt ta. A tc

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dng dung dch AgNO3 trong NH3 to kt ta mu vng nht. T khi hi ca A ln hn 0,9 nhng nh hn 2,6. A l: A. Axetilen B. Metylaxetilen C. Vinylaxetilen D. A l hp cht c cha O v phn t c cha lin kt ba CC u mch (C = 12; H = 1; O = 16; Ag = 108; Ca = 40) 27. Hn hp A gm 0,15 mol axetilen v 0,3 mol hiro. Dn hn hp qua ng s ng Ni xc tc, un nng, thu c hn hp kh B gm etan, etilen, axetilen v hiro c khi lng phn t trung bnh bng 18. Hiu sut phn ng cng hiro l: A. 66,67% B. 60% C. 83,33% D. 85% (C = 12; H = 1) 28. A l mt hirocacbon. Hiro ha A, thu c hexan. Khi cho 0,02 mol A tc dng ht vi dung dch AgNO3/NH3 th thu c 5,84 gam kt ta. Cng thc ca A l: A. CH3CH2CH2CH2CCH B. CH3CCCH2CCH C. CH2=CHCH2CH2CCH D. HCCCH2CH2CCH (C = 12; H = 1; Ag = 108) 29. A l mt cht c cng thc thc nghim (C3H2)n. Hiro ha A, thu c hexan. Nu cho 3,8 gam A tc dng hon ton vi lng d dung dch AgNO3 trong NH3 th thu c 9,15 gam kt ta mu vng nht. Cng thc ca A l: A. HCCCH=CHCCH B. CH2=CHCCCCH C. CH2=C=CHCH2CCH D. HCCCH2CCCH3 (C = 12; H = 1; Ag = 108) 30. Hn hp A gm hai cht hu c dng kh lin tip trong dy ng ng ankin. Qua th nghim cho thy 5,1 gam A tc dng va dung dch brom c ha tan 0,22 mol brom to dn xut tetrabrom ca ankan. Phn trm th tch mi cht trong hn hp 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. Thc hin phn ng trng hp 224 lt kh axetilen (o 27,3C; 836 mmHg), thu c 208 gam cupren, l mt polime c dng lm cht cch in, cch nhit. Hiu sut phn ng trng hp axetilen l: A. 60% B. 70% C. 80% D. 90% (C = 12; H = 1) 32. Ngi ta thc hin phn ng tam hp axetilen to benzen bng cch un nng bnh kn ng kh axetilen, c bt than lm xc tc, 600C. Sau khi a nhit bnh v nh lc u. Coi th tch bnh khng thay i, cht xc tc v benzen lng to ra chim th tch khng ng k, ngi nhn thy p sut trong bnh gim 2,5 ln so vi trc khi phn ng. Hiu sut phn ng iu ch benzen t axetilen l: A. 90% B. 85% C. 70% D. 60% 33. T vi c th iu ch nha PVC (poli vinyl clorua) theo s : 90% 80% vi HS Vi sng HS HS 100% 70% 85% Canxi cacbua Axetilen HS Vinyl clorua HS PVC Khi lng vi cha 80% CaCO3 cn dng sn xut c 2 tn PVC l: A. 7,47 tn B. 5,976 tn C. 9,337 tn D. 6,15 tn (Ca = 40; C = 12; O = 16; H = 1; Cl = 35,5)