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CHUYN 4 :

PHNG PHP GII BI TP V HIROCACBON THM

Phng php gii

I. Phn ng th (ph n ng clo ha, brom ha, nitro ha)

Nhng lu khi lm cc bi tp lin quan n phn ng th ca hirocacbon thm : + Ph n ng clo ha, brom ha (to, Fe) hoc phn ng nitro ha (to, H2SO4 c) i vi hirocacbon thm phi tun theo quy tc th trn vng benzen. + Phn ng clo ha, brom ha c th xy ra phn mch nhnh no ca vng benzen khi iu kin phn ng l nh sng khuch tn v un nng (i vi brom). + Trong bi ton lin quan n phn ng nitro ha th sn phm thu c thng l hn h p cc ch t, v v y ta nn s dng phng php trung b nh tnh ton.

Cc v d minh ha
V d 1: Lng clobenzen thu c khi cho 15,6 gam C6H6 tc d ng ht vi Cl2 (xc tc bt Fe) vi hiu su t phn ng t 80% l : A. 14 gam. B. 16 gam. C. 18 gam. D. 20 gam. Hng dn gii
15,6 .80% = 0,16 mol. 78 Phng trnh phn ng : nC H
6 6 (p )

t , Fe C6H6 + Cl2 C6H5Cl + HCl (1) 0,16 mol: 0,16 Vy kh i lng clobenzen thu c l : 0,16.112,5= 18 gam. p n C.

V d 2: Hn hp g m 1 mol C6H6 v 1,5 mol Cl2. Trong iu kin c xc tc bt Fe, to, hiu sut 100%. Sau phn ng thu c cht g ? bao nhiu mol ? A. 1 mol C6H5Cl ; 1 mol HCl ; 1 mol C6H4Cl2. B. 1,5 mol C6H5Cl ; 1,5 mol HCl ; 0,5 mol C6H4Cl2. C. 1 mol C6H5Cl ; 1,5 mol HCl ; 0,5 mol C6H4Cl2. D. 0,5 mol C6H5Cl ; 1,5 mol HCl ; 0,5 mol C6H4Cl2. Hng dn gii T l mol

n Cl
6

nC H

= 1,5 phn ng to ra hn hp hai sn phm l C6H5Cl v C6H4Cl2

Phng trnh phn ng : Phng trnh phn ng : mol: mol: C6H6 + Cl2 x x C6H6 + 2Cl2 2y y
t , Fe C6H5Cl + x
t , Fe C6H4Cl2 + y
o

HCl x

(1)

2HCl (2) 2y

Phng php hc tt mn ha hc l : Chm ch nghe ging, chm hc l thuyt, chm lm bi t p, chm n bi c

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x + y = 1 x = 0,5 Theo gi thit ta c : x + 2y = 1,5 y = 0,5 Vy sau phn ng thu c 0,5 mol C6H5Cl ; 1,5 mol HCl ; 0,5 mol C6H4Cl2. p n D.
V d 3: M t hp cht hu c X c vng benzen c CTGN l C3H2Br v M = 236. G i tn hp cht ny bit rng hp cht ny l sn phm chnh trong phn ng gia C6H6 v Br2 (xc tc Fe). A. o- hoc p-ibrombenzen. B. o- ho c p-ibromuabenzen. C. m-ibromuabenzen. D. m-ibrombenzen. Hng dn gii t CTPT ca hp cht X l (C3 H2Br)n suy ra (12.3+2+80).n = 236 n = 2. Do cng thc phn t c a X l C6H4Br2. V hp cht X l sn phm chnh trong phn ng gia C6 H6 v Br2 (xc tc Fe) nn theo quy tc th trn vng benzen ta th y X c th l o- ibrombenzen ho c p-ibrombenzen. p n A. V d 4: Hirocacbon X l ng ng ca benzen c phn trm khi lng cacbon bng 90,56%. Bit khi X tc dng vi brom c hoc khng c mt bt st trong m i trng hp ch thu c m t d n xut monobrom duy nht. Tn ca X l : A. Toluen. B. 1,3,5-trimetyl benzen. C. 1,4-imetylbenzen. D. 1,2,5-trimetyl benzen. Hng dn gii t cng thc phn t ca X l CnH2n-6 (n > 6) Theo gi thit ta c :
12n 90,56 = n = 8 V y X c cng thc phn t l C8 H12. 2n 6 100 90,56

V X tc dng vi brom c hoc khng c mt bt st trong mi trng hp ch thu c m t d n xut monobrom duy nht nn tn c a X l: 1,4-imetylbenzen. p n C. V d 5: t chy hon ton a gam hirocacbon X thu c a gam H2O. Trong phn t X c vng benzen. X khng tc d ng vi brom khi c mt bt Fe, cn khi tc d ng vi brom un nng to thnh dn xu t cha 1 nguyn t brom duy nht. T khi hi c a X so vi khng kh c gi tr trong kho ng t 5 n 6. X l A. Hexan. B. Hexametyl benzen. C. Toluen. D. Hex-2-en. Hng dn gii t cng thc phn t ca X l CxHy Phng trnh phn ng :
y y to C x H y + (x + )O2 xCO2 + HO 4 2 2 a a y . mol: 12x + y 12x + y 2

(1)

Theo (1) v gi thit ta c :

a y a x 2 . = = 12x + y 2 18 y 3

Vy cng thc n gin nht c a X l C2 H3, cng thc phn t ca X l (C2H3)n. V t khi hi ca X so vi khng kh c gi tr trong kho ng t 5 n 6 nn ta c : 29.5 < 27n < 29.6 5,3 < n < 6,4 n = 6 cng thc phn t c a X l C12H18. 2
Phng php hc tt mn ha hc l : Chm ch nghe ging, chm hc l thuyt, chm lm bi t p, chm n bi c

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Trong phn t X c vng benzen. X khng tc d ng vi brom khi c mt bt Fe, cn khi tc dng v i brom un nng to thnh dn xu t cha 1 nguyn t brom duy nht nn tn c a X l : Hecxametyl benzen. p n B. V d 6: TNT (2,4,6- trinitrotoluen) c iu ch b ng phn ng c a toluen vi h n hp gm HNO3 c v H2SO4 c, trong iu kin un nng. Bit hiu sut c a ton b qu trnh tng hp l 80%. Lng TNT (2,4,6- trinitrotoluen) to thnh t 230 gam toluen l A. 550,0 gam. B. 687,5 gam. C. 454,0 gam. D. 567,5 gam. Hng dn gii Phng trnh phn ng :
H2 SO 4 ac, t (1) C6H5CH3 + 3HNO3 C6H2(NO2)3CH3 + 3H2O 227 gam: 92 gam: 230.80% x Theo phng trnh v gi thit ta th y kh i lng TNT (2,4,6-trinitrotoluen) to thnh t 230 gam toluen vi hiu su t 80% l :
o

x= p n C.

230.80%.227 = 454 gam. 92

V d 7: Nitro ha benzen c 14,1 gam hn hp hai cht nitro c kh i lng phn t hn km nhau 45 vC. t chy hon ton hn hp hai cht nitro ny c 0,07 mol N2. Hai cht nitro l: A. C6H5NO2 v C6H4(NO2)2. B. C6H4(NO2)2 v C6H3(NO2)3. C. C6H3(NO2)3 v C6H2(NO2)4. D. C6H2(NO2)4 v C6H(NO2)5. Hng dn gii t cng thc phn t trung bnh ca hai hp cht nitro l C6 H6 n (NO2 )n S phn ng chy :
2 C6 H 6 n (NO2 )n 6CO2 +

O , to

6n n H2O + N2 2 2
n 14,1 . 2 78 + 45n

(1)

mol:

14,1 78 + 45n

Theo (1) v theo gi thit ta c :

n 14,1 . = 0, 07 n = 1, 4 2 78 + 45n

Theo gi thit hn hp hai cht nitro c khi lng phn t hn km nhau 45 vC nn phn t ca chng hn km nhau m t nhm -NO2. Cn c vo gi tr s nhm NO2 trung bnh l 1,4 ta suy ra hai hp cht nitro c cng thc l C6H5NO2 v C6H4(NO2)2. p n A.

Phng php hc tt mn ha hc l : Chm ch nghe ging, chm hc l thuyt, chm lm bi t p, chm n bi c

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V d 8: Nitro ho bezen thu c hn hp 2 cht hu c X v Y, trong Y nhiu hn X m t nhm NO2. t chy hon ton 12,75 gam hn hp X, Y thu c CO2, H2O v 1,232 lt N2 (ktc). Cng thc phn t v s mol X trong hn hp l : A. C6H5NO2 v 0,9. B. C6H5NO2 v 0,09. C. C6H4(NO2)2 v 0,1. D. C6H5NO2 v 0,19. Hng dn gi i t cng thc phn t trung bnh ca hai hp cht nitro l C6 H6 n (NO2 )n S phn ng chy :
2 C6 H 6 n (NO2 )n 6CO2 +

O , to

6n n H2O + N2 2 2

(1)

mol:

12,75 78 + 45n

n 12, 75 . 2 78 + 45n n 12, 75 . = 0, 055 n = 1,1 2 78 + 45n

Theo (1) v theo gi thit ta c :

Theo gi thit hn hp hai cht nitro hn km nhau mt nhm NO2. Cn c vo gi tr s nhm NO2 trung bnh l 1,1 ta suy ra hai hp cht X v Yc cng thc l C6 H5NO2 v C6H4(NO2)2. Tng s mol ca hn hp X v Y l p dng s ng cho :

12,75 78 + 45n

= 0,1 mol .

n C H NO
6 5

1 1,1

2 1,1 = 0,9

n C H NO
6 5

nC H
6

4 (NO 2 )2

0,9 9 = 0,1 1

nC H
6

4 (NO2 )2

2
4 (NO2 )2

1,1 1= 0,1 =
9 .0,1 = 0, 09 mol. 10

Vy ch n s mol c a n C H
6

p n B.

II. Phn ng trng hp

V d 10: Tin hnh trng hp 10,4 gam stiren c hn hp X gm polistiren v stiren (d). Cho X tc dng vi 200 ml dung dch Br2 0,15M, sau cho dung KI d vo thy xut hin 1,27 gam iot. Hiu sut trng hp stiren l : A. 60%. B. 75%. C. 80%. D. 83,33%. Hng dn gi i
10, 4 1,27 = 0,1 mol; n Br = 0,15.0,2 = 0,03 mol; n I = = 0, 005 mol. 8 8 2 2 104 254 Phng trnh phn ng : nC H =
nCH=CH 2
|

xt, t o

CH CH2
|

(1)
n

C6 H5

C6 H5

mol:

0,075

Phng php hc tt mn ha hc l : Chm ch nghe ging, chm hc l thuyt, chm lm bi t p, chm n bi c

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C 6 H 5 CH = CH 2 + Br2

C 6 H 5 CH CH 2 Br
|

(2)

Br

mol: KI mol:

0,025 + Br2 0,005

0,025
KBr + I2

(3)

0,005

Theo (3) ta thy s mol Br2 d l 0,005 nn s mol brom phn ng (2) l 0,025 mol v bng s mol ca stiren d. Vy s mol stiren tham gia phn ng trng hp l 0,075 mol, hiu su t phn 0,075 .100 = 75%. ng trng hp l 0,1 p n B. V d 11: hiro ho etylbenzen ta c stiren; trng hp stiren ta c polistiren vi hiu sut chung 80%. Khi lng etylbenzen cn dng sn xut 10,4 tn polisitren l : A.13,52 tn. B. 10,6 tn. C. 13,25 tn. D. 8,48 tn. Hng dn gii S phn ng :
H2 ,t ,xt t , p,xt nC6 H5CH=CH2 nC6 H5CH2CH3
o
o

CH CH 2 C6 H5
| n

gam: tn:

106n

104n

x.80% 10,4 Vy kh i lng etylbenzen cn dng sn xu t 10,4 tn polisitren vi hiu sut 80% l : x=
10, 4.106n = 13,25 tn. 104n.80%

p n C.

III. Ph n ng oxi ha Phng php gii

Nhng lu khi lm cc bi tp lin quan n phn ng oxi ha hirocacbon thm : + Phn ng oxi ha khng hon ton : Benzen khng b oxi ha b i dung dch KMnO4, cc ng ng ca benzen b oxi ha bi KMnO4 khi un nng. V d : C6H5CH3
KMnO4 , H 2 O

80-1000 C

C 6 H5 C OK
||

HCl

C 6 H5 C OH
||

O O 5H3C-C6H4-CH3 + 12KMnO4 + 18H2SO4 5HOOC-C6H4-COOH + 6K2SO4 + 12MnSO4 +28H2O

C6H5-CH2-CH2-CH3 + 2KMnO4+3H2SO4 C6H5COOH + CH3COOH + K2SO4 + 2MnSO4 + 4H2O + Phn ng oxi ha hon ton : Trong phn ng oxi ha hon ton benzen v cc ng n CO2 n H2O ng ca benzen ta c n C H = . n 2 n 6 3

Cc v d minh ha
Phng php hc tt mn ha hc l : Chm ch nghe ging, chm hc l thuyt, chm lm bi t p, chm n bi c

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V d 12: oxi ho ht 10,6 gam o-xylen (1,2-imetylbenzen) cn bao nhiu lt dung d ch KMnO4 0,5M trong mi trng H2SO4 lo ng. Gi s dng d 20% so vi lng phn ng. A. 0,48 lt. B. 0,24 lt. C. 0,12 lt. D. 0,576 lt. Hng dn gii Phng trnh phn ng : 5H3C-C6H4-CH3 + 12KMnO4 + 18H2SO4 5HOOC-C6H4-COOH + 6K2SO4 + 12MnSO4 +28H2O 0,1 mol 0,24 mol Theo phng trnh v gi thit ta c : n KMnO4 = 0,24 + 0,24.20% = 0,288 mol

0,288 = 0,576 lt. 0,5 Ch : Nu dng phng php bo ton electron th nhanh h n. Mn +7 + 5e Mn +2 2C3 2C +3 + 12e Nn 5.nKMnO 4 = 12.n o xilen , t suy ra kt qu.
Vy Vdd KMnO =
4

p n D. V d 13: t chy ht m gam 2 ng ng c a benzen A, B thu c 4,05 gam H2O v 7,728 lt CO2 (ktc). Gi tr ca m v s t ng s mol ca A, B l : A. 4,59 v 0,04. B. 9,18 v 0,08. C. 4,59 v 0,08. D. 9,14 v 0,04. Hng dn gii t cng thc phn t trung bnh ca A v B l : C n H2n 6 Theo gi thit ta c : n H O =
2

4,05 7,728 = 0,225 mol; nCO = = 0,345 mol. 2 18 22,4

Kh i lng ca hai cht A, B l : m = m C + m H = 0,225.2 + 0,345.12 = 4, 59 gam. Phng trnh phn ng :

3n 3 to O2 (1) n CO2 + (n 3) H2O 3 Theo phng trnh phn ng ta th y tng s mol c a hai cht A, B l :

C n H 2n 6

n A, B =

n CO2 n H2O 3

0,345 0,225 = 0, 04 mol. 3

p n A. V d 14: t chy ht 9,18 gam 2 ng ng ca benzen A, B thu c 8,1 gam H2O v V lt CO2 (ktc). Gi tr ca V l : A. 15,654. B. 15,465. C. 15,546. D. 15,456. Hng dn gii t cng thc phn t trung bnh ca A v B l : C n H2n 6 Phng trnh phn ng :
C n H 2n 6

3n 3 to O2 n CO2 3

(n 3) H2O

(1)

Theo gi thit ta c :

Phng php hc tt mn ha hc l : Chm ch nghe ging, chm hc l thuyt, chm lm bi t p, chm n bi c

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n H2O =

8,1 = 0,45 mol m H = 0, 45.2 = 0,9 gam 18 m C = 9,18 0, 9 = 8, 28 gam n CO2 = n C = 8,28 = 0,69 mol. 12

Vy th tch CO2 thu c l : 0,69.22,4=15,456 lt. p n D. V d 15: t chy ht 9,18 gam 2 ng ng k tip thu c dy c a benzen A, B thu c H2O v 30,36 gam CO2. Cng thc phn t ca A v B ln lt l : A. C6H6 ; C7H8. B. C8H10 ; C9H12. C. C7H8 ; C9H12. D. C9H12 ; C10H14. Hng dn gii t cng thc phn t trung bnh ca A v B l : C n H2n 6 Phng trnh phn ng :
C n H 2n 6

mol:

3n 3 to O2 n CO2 3 xn

(n 3) H2O

(1)

n = 8, 625 (14n 6)x = 9,18 Theo (1) v gi thit ta c : x = 0, 08 nx = 0,69 Vy Cng thc phn t ca A v B ln lt l C8H10 v C9 H12. p n B.

V d 16: t chy hon ton m t th tch hi hp cht hu c A cn 10 th tch oxi (o cng iu kin nhit v p sut), sn phm thu c ch gm CO2 v H2O vi m CO2 : m H2O = 44 : 9. Bit MA < 150. A c cng thc phn t l : A. C4H6O. B. C8H8O. C. C8H8. D. C2H2. Hng dn gii T gi thit m CO2 : m H2O = 44 : 9 suy ra : n CO : n H O = 1 : 0,5 n C : n H = 1 : 1.
2 2

A c th c hoc khng c oxi, t cng thc phn t ca A l CxHxOy. Phng trnh phn ng : 5x y x to CxHxOy + ( ) O2 H2O (1) xCO2 + 4 2 2 mol: 1

( 5x y ) 4 2

x = 8 5x y ) =10 4 2 y = 0 Vy cng th c phn t c a A l C8H8. p n C.

Theo (1) v gi thit ta c : (

Phng php hc tt mn ha hc l : Chm ch nghe ging, chm hc l thuyt, chm lm bi t p, chm n bi c

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V d 17: t chy hon ton hirocacbon X cho CO2 v H2O theo t l mol 1,75 : 1 v th tch. Cho bay hi hon ton 5,06 gam X thu c m t th tch hi ng bng th tch ca 1,76 gam oxi trong cng iu kin. Nhn xt no sau y l ng i vi X ? A. X khng lm mt mu dung d ch Br2 nhng lm mt mu dung dch KMnO4 un nng. B. X tc d ng v i dung dch Br2 to kt t a trng. C. X c th trng hp thnh PS. D. X tan t t trong nc. Hng dn gii Theo gi thit t chy hon ton X cho n CO : n H O = 1,75 : 1 n C : n H = 1,75 : 2 = 7 : 8.
2 2

t cng thc phn t ca X l (C7H8)n. Theo gi thit ta c :

n X = nO =
2

1, 76 5, 06 = 0, 055 mol M X = = 92 gam / mol (12.7 + 8)n = 92 n = 1 32 0, 055

Vy cng th c phn t c a X l C7H8. Nhn xt ng i vi X l : X khng lm mt mu dung dch Br2 nhng lm mt mu dung d ch KMnO4 un nng (X l toluen: C6 H5CH3). p n A. V d 18: A, B, C l ba cht hu c c %C, %H (theo khi lng) ln lt l 92,3% v 7,7%, t l khi lng mol tng ng l 1: 2 : 3. T A c th iu ch B hoc C bng mt phn ng. C khng lm mt mu nc brom. t 0,1 mol B ri dn ton b sn phm chy qua b nh ng dung dch nc vi trong d. a. Khi lng bnh tng ho c gim bao nhiu gam ? A. Tng 21,2 gam. B. Tng 40 gam. C. Gim 18,8 gam. D. Gim 21,2 gam. b. Khi lng dung d ch tng hoc gim bao nhiu gam ? A. Tng 21,2 gam. B. tng 40 gam. C. gim 18,8 gam. D. gim 21,2 gam. Hng dn gii Theo gi thit ta th y A, B, C c cng cng thc n gin nht.
92,3 7, 7 : = 1:1 . Cng thc n gin nht c a A, B, C l CH. 12 1 T A c th iu ch B ho c C b ng mt phn ng; C khng lm mt mu nc brom nn A l C2H2, B l C4H4; C l C6 H6 (benzen). S t chy B : nC : nH =
O2 ,t C4H4 (1) 4CO2 + 2H2O mol: 0,1 0,4 0,2 Dn ton b sn phm chy vo bnh ng nc vi trong d th xy ra phn ng : CO2 + Ca(OH)2 CaCO3 + H2 O (2) 0,4 mol: 0,4 Kh i lng b nh nc vi trong tng b ng tng kh i lng c a CO2 v H2O = 0,4.44 + 0,2.18= 21,2 gam. Kh i lng kt ta bng 0,4.100 = 40 gam. Nh v y khi lng kt t a tch ra kh i dung d ch ln hn kh i lng nc v CO2 nn kh i lng dung d ch gim l 40 21,2 =18,8 gam. p n AC.
o

Phng php hc tt mn ha hc l : Chm ch nghe ging, chm hc l thuyt, chm lm bi t p, chm n bi c