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VI. AREN (HIROCACBON THM)

VI.1. nh ngha Aren hay hirocacbon thm l mt loi hirocacbon m trong phn t c cha t nht mt nhn thm (nhn benzen) VI.2. Cng thc tng qut (CnH2n + 2 - 8 - m) CnH2n - 6 - m CnH2n - 6 - 2k n6 m: nguyn dng chn, c th bng 0 m = 0; 2; 4; 6; 8; 10; ... (n 6; k = 0; 1; 2; 3; 4; ...)

Hirocacbon thm cha mt nhn thm, ngoi nhn thm l cc gc no mch h (ng ng benzen): CnH2n - 6 (n 6)

Ch l c th p dng cng thc CnH2n - 6 - m xc nh cng thc phn t cho mi loi hirocacbon thm (mt nhn thm hay nhiu nhn thm, gc hirocacbon lin kt vo nhn thm c th l gc no hay khng no, mch h hay vng); Cn cng thc CnH2n - 6 ch p dng ng cho loi hirocacbon thm ng ng benzen (ch c mt nhn thm duy nht, gc hirocacbon lin kt vo nhn thm, nu c, l cc gc no, mch h). Hoc bt u vi cng thc ca ankan (alcan) vi n nguyn t C th s nguyn t H ti a tng ng l (2n + 2), to mt nhn benzen th tr 8 nguyn t H (gm 1 vng, 3 ni i), nu ngoi nhn thm c thm mt lin kt i na th chng ta tr tip 2 nguyn t H to lin kt i C=C nm bn ngoi nhn thm, hoc nu c lin kt ba CC th tr 4 nguyn t H, mt vng th tr tip 2 nguyn t H;

Bi tp 43 Xc nh CTPT ca cc cht sau y:

CH3 CH=CH2 CH2 CH=CH2

CH

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Bi tp 43 Xc nh phn t lng ca cc cht sau y:

CH3 CH CH3 CH3 CH2 HC CH2 C CH

(C = 12; H = 1)

VI.3. Cch c tn
Coi cc gc hirocacbon gn vo nhn thm nh l cc nhm th gn vo benzen. Hai nhm th gn vo v tr 1,2 cn gi l v tr orto (o - ); Hai nhm th gn vo v tr 1,3 cn gi l v tr meta (m - ); Hai nhm th gn vo v tr 1,4 cn gi l v tr para (p - ). Thng hirocacbon thm c tn thng thng, nn thuc lng, nh toluen, xilen, stiren, naptalen, antraxen, cumen, mesitilen,... CH3 CH3 CH3 CH CH2 CH3 CH

Benzen ( CnH2n - 6 ) C6H6

Vinylbenzen Stiren ( CnH2n - 6 - m ) Isopropylbenzen Cumen ( Cn H2n - 6 ) C9H12 C8H8

1, 2

Dimetylben zen o Xilen ( CnH2n - 6 ) C8H10

CH3

CH3 Naptalen ( CnH2n - 6 - m ) C10H8

1, 3

m C8H10

CH3 Dimetylbenzen Xilen

CH3 Dimetylbenzen p Xilen C H 8 10

1, 4

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CH3

CH2=CH CH2

H3C CH3 1,3,5-Trimetylbenzen Mesitilen C9H12

Antraxen (CnH2n - 6 - n ) C14H10 Phenantren C14H10

C CH

1-Etinyl-2-phenyl-4-alylbenzen C17H14

Bi tp 44 Xc nh CTPT v tnh khi lng phn t ca cc cht sau y: a. Mesitilen (1,3,5-Trimetylbenzen) b. p-Xilen (1,4-imetylbenzen) c. Stiren (Vinylbenzen) d. Naptalen e. Biphenyl (Phenylbenzen) f. Phenylaxetilen (Etinylbenzen) g. Axit picric (2,4,6-Trinitrophenol) h. p-Toluiin (1-Amino-4-metylbenzen) i. o-Clorotoluen (1-Clo-2-metylbenzen) j. Benzoyl clorua (C6H5COCl) k. Axit salixilic (Axit o-hidroxibenzoic) l. Ru benzylic (Phenylmetanol) (C = 12; H = 1; O = 16; N = 14; Cl = 35,5) Bi tp 44 Hy xc nh CTPT v khi lng phn t ca cc cht sau y: a. Toluen (Metylbenzen) b. o-Xilen c. p-Ximen (p-Metylisopropylbenzen) d. Cumen (Isopropylbenzen) e. Antraxen f. Phenantren g. Duren (1,2,4,5-Tetrametylbenzen) h. 1-Vinyl-3-etinyl-5-alylbenzen i. p-Phenylxiclohexylbenzen j. Benzanehit (Phenylmetanal) k. Axit tereptalic (Axit 1,4-benzenicacboxilic) l. Axit benzoic (Axit benzencacboxilic) (C = 12; H = 1; O = 16)

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VI.4. Tnh cht ha hc

S d gi loi hirocacbon ny l hirocacbon thm v hu ht chng c mi thm c trng. V phng din cu to, phn t loi ny c cha t nht mt nhn thm (nhn benzen). V tnh cht ha hc, ngi ta ni aren c tnh thm v phng din ha hc. y l tnh cht nhn thm cho c phn ng cng, nhng kh cng hn so vi hirocacbon khng no thng thng; nhn thm cho c phn ng th (phn ng th i in t hay thn in t) v tng i d th; nhn thm bn vi tc nhn oxi ha. C th tm gn tnh thm v phng din ha hc nh sau: kh cng, d th v bn vi tc nhn oxi ha. Nguyn nhn ca tnh cht ha hc ny l do s linh ng ca in t trong nhn thm, cc in t lan truyn trn khp 6 nguyn t cacbon ca nhn thm, khin cho lin kt gia C vi C trong nhn thm khng hn l mt lin kt i, cng khng hn l mt lin kt n, m c tnh cht trung gian gia mt lin kt i v mt lin kt n [dC-C = 1,54 ; dC=C = 1,34 ; d(C-C)benzen = 1,40 ]. in t hin din nhiu trong nhn thm nn cc tc nhn i in t (thn in t) d th vo nhn thm. in t lan truyn trn khp nhn thm (ch khng tp trung ti mt v tr xc nh, hiu ng cng hng) nn nhn thm tng i bn vi tc nhn oxi ha (nh dung dch KMnO4 khng oxi ha c nhn thm, khng ph hy c nhn benzen). Ch l phn ng th vo nhn thm l phn ng th i in t (thn in t), cn phn ng th vo vo ankan l phn ng th dy chuyn theo c ch gc t do.
0 0 0

VI.4.1. Phn ng chy

CnH2n - 6 - m + (
Aren

3n 3 m )O2 2 2 4
(

t0

nCO2

+ (n-3 -

m )H2O 2

CnH2n - 6

3n 3 )O2 2

t0

nCO2 + (n - 3)H2O

Aren ng ng benzen

VI.4.2. Phn ng cng hiro

Th d: C6 H 6 +
Benzen

3H2

Ni (Pt), t0

Hiro

Xiclohexan

C6H12

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+ Bezen ( C6H6 ) CH3 Toluen ( C7H8 )

3H2 Hidro + 3H2

Ni, t0 Xiclohexan ( C6H12 ) Ni, t0 CH3 Metyl xiclohexan ( C7H14)

CH Stiren ( C8H8 ) CH2

CH2

H2

Ni, t0

CH2

CH3

Etyl benzen ( C8H10 ) CH3 + 3H2 Ni, t0 CH2 CH3

Etyl benzen ( C8H10 )

Etyl xiclohexan ( C8H16 )

Qua phn cng hiro vo stiren trn ta thy hiro cng vo lin kt i C=C ngoi nhn thm trc, sau hiro mi cng vo nhn thm. iu ny chng t cng vo lin kt i thng thng d hn l cng vo nhn thm.
VI.4.3. Phn ng cng halogen X2 halogen X2 cng c vo nhn thm th cn dng halogen X2 nguyn cht v cn chiu sng hay un nng.

Th d:
Cl + Benzen ( C6H6 ) 3Cl2 Clo ah sag n n ( t0 ) Cl Cl 1,2,3,4,5,6 - Hexaclo xiclohexan (C6H6Cl6) Hexacloran (Thuo tr u 666) c sa Br Br Br Br Cl Cl Cl

+ Benzen ( C6H6 )

3Br2

as ( t0 )

Brom nguye cha n t

Br Br 1,2,3,4,5,6- Hexabrom xiclohexan ( C6H6Br6 )

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VI.4.4. Phn ng th bi halogen X2 (Cl2, Br2)

nguyn t H ca nhn thm c th bi nguyn t X (ca X2) th cng cn dng X2 nguyn cht v dng cht xc tc l bt st (Fe) hay mui st (III) halogenua (FeX3). Th du:
Cl + (C6H6)
Benzen

Cl 2
Clo

Fe (FeCl 3) (C6H5Cl)

HCl
Hiro clorua

Clo benzen; Phenlyl clorua

Br2

Fe (FeBr3)

Br
Brom benzen Phenyl bromua

HBr

Brom (nguye cha) n t

Hiro bromua

Br + Br2
Brom benzen

Fe Br

Br Br

Br

HBr

Brom (nguye cha) n t o - ibrom benzen p - ibrom benzen

Hrro bromua

CH3 Cl + CH3 +
Toluen Metyl benzen o - Clo toluen

HCl
Hiro clorua

Cl2
Clo

Fe
1:1

CH3 + Cl HCl

p - Clo toluen

Lu L.1. Benzen khng lm mt mu nu ca nc brom d c s hin din ca cht xc tc hay nh sng. L.2. Benzen ch lm mt mu nu ca brom lng nguyn cht vi s hin din ca nh sng (do c phn ng cng) hay bt st (do c phn ng th).

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Benzen

C6H6

+ + +

Br2 (dd) Nc brom

as , Fe

Benzen

C6H6

3Br2 (nguyn cht) Br2 (nguyn cht)

as

1,2,3,4,5,6-Hexabrom xiclohexan
Fe (FeCl3)

C6H6Br6

(Phn ng cng) + HBr (P th)

Benzen

C6H6

Brom benzen

C6H5Br

Hiro bromua

L.3. Khi cho toluen (C6H5-CH3) tc dng vi clo (Cl2) hay brom (Br2) nu c bt st (Fe)

lm xc tc th c phn ng th H ca nhn thm (th i in t); nu hin din nh sng hay un nng th c phn ng th H ca nhm metyl (CH3) ngoi nhn thm (th theo c ch gc t do).
Fe

CH3
Toluen

Cl2
Clo

CH3
o-Clotoluen

HCl

Cl CH3
p-Clotoluen

Hay

Cl

CH3
Toluen

Cl2
Clo

as t0

CH2Cl
Benzyl clorua

HCl

Hidro clorua

L.4. Qui tc th vo nhn benzen c mang sn nhm th

Khi nhn benzen c mang sn mt nhm th y in t [thng l cc nhm ch cha lin kt n, nh CH3 ( trong toluen C6H5-CH3 ), OH ( trong phenol C6H5-OH ), NH2 (trong anilin C6H5-NH2), Cl (trong clobenzen C6H5-Cl), Br (trong brombenzen C6H5-Br),...] th nhm th th nh s th vo mt, hai hay c ba v tr c nh s 2, 4, 6 i vi nhm y in t (v tr orto, para); Cn khi nhn benzen mang sn mt nhm th rt in t [thng cc cc nhm c cha lin kt i, nh NO2 (trong nitrobenzen C6H5-NO2), COOH (trong axit benzoic C6H5-COOH), SO3H (trong axit benzensunfonic C6H5-SO3H,...] th nhm th th nh s th vo mt hay c hai v tr c nh s 3, 5 i vi nhm rt in t (v tr meta).

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Th du : CH3
+

CH3

Br
+

HBr
Hirobromua

Br2

Fe

o-Bromtoluen

CH3
+

Toluen

Brom (nguye cha) n t

HBr

OH Br
+
6

OH
1 2

p-Bromtoluen

Br

Br
+

3Br2
N brom c
5 4

3HBr
Axit bromhiric

Phenol

Br NO2
+

2,4,6-Tribrom phenol

NO2
+

HNO3()

H2SO4 ()

H2O

Axit nitric a a m c Nitrobenzen

NO2
m-initrobenzen

VI.4.5. Phn ng nitro ha (phn ng th H ca nhn thm bi nhm nitro NO2 ca axit nitric m c HNO3)

Th d:
Benzen

C6H6

+ HNO3() + 3HNO3()

H2SO4(), t0

Nitrobenzen H2SO4 (), t0

C6H5-NO2

+ H 2O + 3H2O

C6H5-CH3
Toluen

2,4,6 - Trinitrotoluen Thuc n TNT H2SO4(), t0

C6H2(NO2)3CH3

Nitrobenzen

C6H5 - NO2

HNO3()

1,3 i nitroenzen m - initrobenzen

C6H4(NO2)2 + H2O

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NO2 + (C6H6)
Benzen

HNO3()
Axit nitric a a m c

H2SO4() t0

+ (C6H5-NO2)
Nitrobenzen

H2O
N c

NO2 +
Nitrobenzen

NO2 HNO3()
H2SO4() t0

+ NO2
m- initrobenzen 1,3- initrobenzen

H2O

CH3 +
Toluen

CH3 3HNO3()
H2SO4() t0

O2N

NO2 + NO2
2,4,6- Trinitrotoluen Thuo no c TNT

3H2O

VI.4.6. Phn ng b oxi ha bi dung dch KMnO4

Nhn thm bn vi tc nhn oxi ha KMnO4, nhng cc gc hirocacbon gn vo nhn thm d b oxi ha bi tc nhn oxi ha KMnO4 trong mi trng axit (thng l H2SO4). Cc gc hirocacbon ny b oxi ha to thnh nhm chc axit hu c COOH (cn trong mi trng trung tnh th nhm chc axit hu c hin din dng mui (do c KOH to ra, nn nhm chc axit hu c hin din dng mui COOK). Trong mi trng axit (H+), KMnO4 b kh to mui mangan (II) (Mn2+); cn trong mi trng trung tnh, KMnO4 b kh to MnO2 (mangan ioxit), mt cht rn khng tan trong nc c mu en.
Benzen

C6H6

Kali pemanganat

KMnO4

H2SO4 + 9H2SO4 5C6H5-COOH

Axit benzoic

5C6H5-CH3
Toluen

6KMnO4

+ 6MnSO4 + 14H2O

+ C6H5-CH3 + 2KMnO4
Toluen

3K2SO4

C6H5COOK
Kali benzoat

+ 2MnO2 +
Mangan ioxit

KOH + H2O

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C6H5-CH=CH2
Stiren

+ 2KMnO4

+ 3H2SO4

C6H5-COOH +
Axit benzoic

CO2 +

2MnSO4 + K2SO4 + 4H2O

KMnO4 H2SO4
Axit sunfuric

CH3 5
Toluen

Benzen

Kali pemanganat

COOH 5
Axit benzoic

+ 6KMnO4 + 9H2SO4

+ 6MnSO4 + 3K 2SO4 + 14H2SO4

CH3 + 2 KMnO4
Toluen Kali benzoat

COOK + 2MnO2 + KOH

Mangan ioxit

CH=CH2 + 2KMnO4 + 3H2SO4

Stiren

COOH + CO2
Axit benzoic

+ 2MnSO4 + 4H2O CH2-CH3 + 22KMnO4 + 33H2SO4 COOH + 5CO2 + 22MnSO4 + 48H2O

Kh cacbonic

5CH3-CH2-CH2
p-Etyln-propylbenzen Axit axetic

5CH3-COOH + 5HOOC
Axit tereptalic

VI.5. ng dng VI.5.1.T benzen iu ch c thuc tr su 666; anilin; phenol; nha phenolfomanehit; stiren; nha PS; cao su buna-S; ...

C6H6 C6H6

+ +

Benzen

3Cl2
Clo

as

1,2,3,4,5,6-Hexacloxiclohexan, Hexacloran, Thuc tr su 666 H2SO4 ()

C6H6Cl6

HNO3 ()

C6H5NO2

H2O + 2H2O

C6H5NO2
C6H6 + Benzen

Nitrobenzen

+ 6[ H ] Fe/HCl Hiro nguyn t mi sinh (ang sinh)

Clo

C6H5-NH2
Anilin

Cl2

Fe

Clobenzen

C6H5Cl

HCl
Hiro clorua

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C6H5Cl

NaOH ()
Dung dch xt m c

t0, xt

Clobenzen

C6H5OH
Phenol

NaCl
Natri clorua

OH (n+2)
Phenol

OH + (n + 1) H-CHO
Fomanehit TN (t , xt)
0

OH CH2
Nh phenolfomanehit a +

OH CH2 n (n+1)H2O

+
Benzen

CH3-CH2-Cl
Cloetan

AlCl 3 Friedel-Crafts

CH2-CH3 + HCl
Etylbenzen Hiro clorua

CH2-CH3

t0, xt (Cr2O3, Al 2O3, 6000C)

CH=CH2 + H2
Stiren TH (t0, xt) Hiro

n
Stiren

CH=CH2

CH CH2

n Hay: + CH2=CH2
Etilen AlCl 3 Polistiren, Nh PS a

CH2-CH3
Etylbenzen

n CH2=CH-CH=CH2 + n CH=CH2
1,3-Butaien Stiren

TH Na

CH2-CH=CH-CH2-CH-CH2
Cao su Buna-S

C6H5

C6H5

VI.5.2. T toluen iu ch c axit benzoic, ru benzylic, thuc n TNT

5C6H5-CH3 + 6KMnO4 + 9H2SO4 5C6H5-COOH + 6MnSO4 + 3K2SO4 +14H2O

Toluen Kali pemanganat Axit benzoic Mangan (II) sunfat

C6H5-CH3
Toluen

Cl2
Clo

as

Benzyl clorua

C6H5-CH2-Cl

HCl
Hiro clorua

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C6H5-CH2-Cl
Benzyl clorua

NaOH (dd)
Dung dch xt

t0

Ru benzylic

C6H5-CH2-OH
CH3

NaCl
Natri clorua

CH3 +
Toluen

3HNO3 ()
Axit nitric a a m c

H2SO4() t0

O2N
5

2 3

NO2 + 3H2O
N c

NO2
2,4,6-Trinitrotoluen Thuo no c TNT

VI.5.3. T p-xilen iu ch c t si polieste

H3C
p- Xilen

CH3 + 5HOOC

12KMnO4

18H2SO4

COOH + 12MnSO4 + 6K 2SO4 28H2O

Axit tereptalic

n HO-C O
Axit tereptalic

C-OH + n HO-CH2-CH2-OH Etylenglicol O C O

T polieste

TN (t0, xt)

C O CH2-CH2 O

+ 2nH2O n

VI.5.3. iu ch V.6.1. Axetilen

Axetilen

Benzen
C 6000C Benzen

3C2H2

C6H6

VI.6.2. Propin

Mesitilen

CH3 3CH3 C CH
Tam hp (t , xt)
0

Propin

1,3,5 - Trimetylbenzen Mesitilen

H3C

CH3

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VI.6.3. n - Hexan
n- Hexan

Benzen
t0, xt Benzen

CH3-CH2-CH2-CH2-CH2-CH3

C6H6

4H2

Hiro

VI.6.4. Xiclohexan
t0 xt Xiclohexan

Benzen

+
Benzen

3H2
Hiro

VI.6.5. M etylxiclohexan

Toluen
t0 xt Toluen

CH3
Metylxiclohexan

CH3

3H2
Hiro

VI.6.6. n-Heptan

Toluen
t0 xt Toluen

CH3-CH2-CH2-CH2-CH2-CH2-CH3
n-Heptan

CH3 +

4H2
Hiro

VI.6.7. Axetilen

Benzen Etilen;

Stiren
Etilen , AlCl3 (H3PO4)

Axetilen Axetilen

C , 6000C H2/Pd , t0

Etylbenzen

Cr2O3 , Al2O3 ,6000C H2 / Ni , t0

Stiren

Axetilen

HCl / t0, xt

Vinyl clorua

Etyl clorua

Benzen , AlCl3 (P Friedel - Crafts)

Etyl benzen

VI.6.8. Than

Nha than

Cc loi hirocacbon thm

Kh l cc (Kh thp): H2, CH4, NH3,... Than Dung dch amoniac: NH3 ha tan trong nc
Chng ct trong l cc

Nha than : Cha cc loi HC thm, phenol Than cc: C

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T nha than em chng ct phn on c th thu c cc hirocacbon thm nh: Benzen, Toluen, o-Xilen, m- Xilen, p-Xilen,...
Bi tp 45 a. T metan, vit cc phng trnh phn ng iu ch o- clo nitrobenzen v mclo nitrobenzen. b. T canxi v cacbon, vit phng trnh phn ng iu ch p- aminophenol v m- aminophenol. Bi tp 45 a. T qung bauxite (boxit, cha ch yu Al2O3), vit cc phng trnh phn ng iu ch p- brom anilin v m- brom anilin. b. T vi v than, vit phng trnh phn ng iu ch p- amino phenol v mamino brom benzen. Bi tp 46 ( 48 b TSH) Mt hn hp gm ba cht thuc dy ng ng aren l A (CnH2n - 6); B (CnH2n - 6) v C (CmH2m - 6) vi n < n < m , trong A v C c s mol bng nhau v cch nhau k cht trong dy ng ng. Khi t chy x gam hn hp cn dng y gam O2. 1. Hy chng minh rng: 24 x 3 y 48 x 10 y <m< +k 24 x 7 y 24 x 7 y 2. Cho x = 48,8g; y = 153,6g; k = 2 a. Tm cng thc ca A, B, C, bit rng B khng c ng phn l hp cht thm. b. Hy tnh % khi lng mi cht A, B, C trong hn hp. (H = 1; C = 12; O = 16) S: 31,97% C6H6; 18,85% C7H8; 49,18% C9H12 Bi tp 46 12,28 gam hn hp A gm hai cht X, Y k tip nhau trong dy ng ng stiren. t chy hon ton lng hn hp A trn ri cho tt c sn phm chy hp th vo bnh ng 2 lt dung dch Ba(OH)2 0,25M. Trong bnh c to 11,82 gam kt ta. Nu un nng dung dch trong bnh sau khi hp th sn phm chy th thu c thm kt ta na. a. Xc nh CTPT ca X, Y. b. Tnh % khi lng mi cht trong hn hp A. c. Xc nh CTCT ca X, Y. c tn X, Y. Bit rng nu em oxi ha hn hp A bng dung dch KMnO4 trong mi trng axit H2SO4 th thu c hn hp hai axit hu c, trong c axit tetreptalic v c kh CO2 thot ra. Vit cc phng trnh phn ng xy ra. Cc phn ng xy ra hon ton. (C = 12; H = 1; O = 16; Ba = 137) S: a) C8H8 ; C9H10; b) 42,35% C8H8 ; 57,65% C9H10 c) C6H5-CH=CH2 p-CH3-C6H4-CH=CH2

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Bi tp 47 Nhn bit: n-hexan; benzen; toluen; stiren; 1-hexin (hexin-1) v 1-hexen (hexen-1) ng trong cc bnh khng nhn. Bi tp 47 Phn bit: metan; etilen; axetilen; vinyl axetilen; benzen v stiren bng mt dung dch ha cht duy nht. Bi tp 48 1500C, hn hp hi mt aren Y thuc dy ng ng benzen v oxi (ly d), trong Y chim 5% th tch, c np vo mt kh nhin k, to p sut 1atm. Sau khi bt tia la in t chy hon ton Y ri a v nhit ban u, p sut trong bnh l 1,05atm. a. Xc nh CTPT, vit CTCT c th c ca X, Y, Z v gi tn chng (X, Z ln lt l ng ng lin trc v lin sau ca Y). b. Trn ring r X, Y vi clo trong hai bnh thy tinh A, B ri a ra nh sng v un si. D on phn ng xy ra. c. Cho Z tc dng vi hn hp sunfocromic (K2Cr2O7/H2SO4) th c CO2 thot ra. Xc nh CTCT ng ca Z v vit phng trnh phn ng. d. Nu ehiro ha Z, vi cu to cu c, ri cho sn phm tc dng vi HCl th thu c sn phm g? Gi tn. Nu em trng hp sn phm th thu c cht g? Vit phn ng. S: a. X: C6H6; Y: C7H8; Z: C8H10 c. Z: Etylbenzen d. Stiren Bi tp 48 Hn hp A gm hi mt aren X (ng ng benzen) v oxi, trong th tch oxi chim gp 14 ln th tch hi X. Cho hn hp A vo mt bnh kn 1600C, to p sut p1. Bt tia la in t chy ht X trong hn hp A. Sau phn ng chy, gi nhit bnh 1600C, p sut trong bnh tng 10% so vi p1. a. Xc nh CTPT ca aren X. Cho bit th tch bnh khng thay i. b. X tc dng dung dch KMnO4 trong mi trng axit H2SO4 c to kh CO2. Xc nh CTCT X. c tn X. Vit CTCT cc ng phn thm ca X. c tn cc ng phn ny. c. C th gn gc hirocacbon vo nhn thm theo phn ng Friedel-Crafts nh sau: Ar-H + R-Cl AlCl3 Ar-R + HCl

Vit phng trnh phn ng iu ch X t metan. Cc cht v c, xc tc coi nh c sn. d. T X, thc hin phn ng ehiro ha thu c cht Y. Trng hp Y thu c mt polime. Xc nh h s trng hp ca polime ny nu khi lng phn t ca polime ny l 416 000vC. (C = 12; H = 1) S: X: C8H10 , Etylbenzen Y: Stiren n = 4 000

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CU HI N PHN VI
1. Aren l g? Ly hai th d minh ha. 2. Vit cng thc tng qut ca: ng ng benzen; ca hirocacbon thm; ca stiren. 3. Vit CTCT ca cc hirocacbon thm sau y: Benzen; Toluen; o-Xilen; m-Xilen; pXilen; Cumen; Mesitilen; Naptalen; Antraxen; Stiren; p-Ximen; Phenantren; Biphenyl. 4. Cng thc CnH2n-6 c phi l cng thc tng qut ng cho mi hirocacbon thm hay khng? Cng thc t nh trn ng trong trng hp no? 5. Hy cho bit hirocacbon thm no khng c cht ng phn l hp cht thm? 6. Vit CTCT cc ng phn thm cc cht c CTPT C9H12. c tn cc ng phn ny. 7. Ti sao gi cc hp cht c cha nhn benzen l cc hp cht thm? 8.
VieCTPT va c te ca h chasau a: t o n c p t y CH2 CH3 CH3 CH 3 CH H3C CH3 C CH CH 2 CH 2 CH CH2 CH CH2 CH2 CH3 CH3 CH3 CH3 CH CH2

9. Vit phng trnh phn ng gia benzen vi cc cht sau y: a. H2 (c Ni lm xc tc, un nng) b. Cl2 (c s hin din ca nh sng) c. Cl2 (c bt st lm xc tc, t l mol nC6H6 : nCl2 = 1:1) d. HNO3() (c H2SO4() lm xc tc) e. Oxi (benzen b oxi ha hon ton) f. Brom nguyn cht theo t l mol 1 : 2 (c bt Fe lm xc tc) g. Metyl clorua (co AlCl3 lam xuc tac, phan ng Friedel - Crafts, gan goc hirocacbon vao nhan thm)

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10. Vit phng trnh phn ng ca toluen vi tng tc cht sau: a. Cl2 (t l mol 1 : 1, c Fe lm xc tc) b. Cl2 (t l mol 1 : 1, c s hin din ca nh sng hay un nng) c. Dung dch kali pemanganat trong mi trng axit H2SO4 d. Dung dch KMnO4 e. Axit nitric m c (t l mol 1 : 3, c H2SO4() lm xc tc) f. Oxi (phn ng chy) g. Hiro kh toluen (c bch kim lm xc tc, un nng) h. Brom lng (t l mol 1 : 3, c FeBr3 lm xc tc) i. Etyl clorua (c AlCl3 xc tc, ly sn phm para) 11. Vit cc phng trnh phn ng theo s sau (mi mi tn l mt phn ng): Benzen Clobenzen Natri phenolat Phenol Xiclohexen 1,2-ibromxiclohexan Xiclohexanol Xiclohexaniol -1,2 12. Tng t nh cu (11) vi: Toluen Benzyl clorua Benzanehit Axit benzoic

Ru benzylic Benzyl benzoat

13. T kh thin nhin, ngi ta ly c kh metan. V t metan c th iu ch c nha phenolfomanehit. Vit cc phng trnh phn ng xy ra. 14. T du m, ngi ta ly n-heptan, t iu ch c toluen. Vit cc phng trnh phn ng iu ch thuc n TNT, axit m-clobenzoic t du m. 15. Vit CTCT cc ng phn thm v c tn cc ng phn ny ng vi CTPT C9H12. 16. A l mt hirocacbon. t chy ht m gam A, thu c 8,96 lt CO2 (ktc) v 4,5g H2O. a. Tnh m b. Vit cc CTCT c th c ca A v c tn cc cht ny. Bit rng t khi hi ca A nh hn 4 v A khng lm mt mu nc brom. (C = 12; H = 1) S: 5,3g; C8H10 ; 4 CTCT 17. A l mt hn hp gm hai cht thuc dy ng ng stiren, c khi lng phn t hn km nhau 14 vC. t chy hon ton m gam A bng Oxi d. Cho sn phm chy hp th vo 300ml dung dch NaOH 2M. Khi lng bnh ng dung dch xt tng 22,44 gam v thu c dung dch D. Cho dung dch BaCl2 d v dung dch D, thu c 35,46 gam kt ta. a. Tnh m. b. Xc nh CTPT ca hai hirocacbon. c. Tnh % khi lng mi cht trong hn hp A. d. Vit CTCT hai hirocacbon trn. Bit rng chng c cht dng cis. Cc phn ng xy ra hon ton.

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(C = 12; H = 1; O = 16; Ba = 137) S: m = 5,48g; 56,93% C8H8 43,07% C9H10

18. T mt cng on ca s chng ct du m, ngi ta ly c n-heptan vi hiu sut 20%. Tnh khi lng ca cng on du m cn dng t c th iu ch c na tn thuc n TNT theo s v hiu sut tng ng nh sau: n-Heptan HS 30% Toluen HS 50% TNT (C = 12; H = 1; N = 14; O = 16) S: 7,342 tn 19. Cht A c CTPT C6H6. Xc nh CTCT ca A nu: a. A khng tc dng vi nc brom. b. Mt mol A tc dng vi lng d dung dch bc nitrat trong amoniac thu c 292 gam cht khng tan c mu vng. c. Mt mol A tc dng vi lng d dung dch AgNO3/NH3 thu c 185 gam kt ta. A c cu to mch h. (C = 12 ; H = 1 ; Ag = 108) S: a) 1 CTCT b) 2 CTCT c) 6 CTCT 20. Hn hp B gm C2H6, C2H4 v C3H4. Cho 12,24 gam hn hp B vo dung dch cha AgNO3 c d trong amoniac, sau khi phn ng xong thu c 14,7 gam kt ta. Mt khc, 4,256 lt kh B (ktc) phn ng va vi 140 ml dung dch brom 1M. Tnh khi lng mi cht trong 12,24 gam B ban u. Cho bit cc phn ng xy ra hon ton. (C = 12 ; H = 1 ; Ag = 108) ( TSH i hc Kin Trc tp HCM, mm 2001) 21. a. Vit cc phng trnh phn ng ha hc, di dng CTCT thu gn, theo dy chuyn ha sau:

Toluen

Cl2, as

B1

NaOH t0

B2

CuO t0

2 B3 dd NH 3

Ag O

B4

CH3OH H2SO4, t 0

B5

b. Vit phng trnh phn ng thy phn ca B5 trong dung dch axit v dung dch baz. Nu c im ca tng phn ng. ( TSH khi B, nm 2005)
22. 1. Vit cc phng trnh phn ng theo s bin ha sau (cc cht hu c vit di dng cng thc cu to):
Br2 , Fe

A1

dd NH3 a, d , t cao, p cao c

A2 A5 A9

dd HCl dd HCl Ag2O/NH3 t0

A3 A6 A10

Toluen
Br2, askt

0 c A4 dd NH3 a, d , t cao, p cao

A7

dd NaOH, t

A8

CuO, t

Bie A 1, A 4, A 7 la c cha og pha co ng th pha t 7H7Br t ca t n n co c n C

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2. Cht hu c B l ng phn ca A3 c cha vng benzen. B khng phn ng vi kim loi kim. Xc nh cng thc cu to ca B. ( TSH khi A, nm 2004)

23. Tnh thm ca hirocacbon thm v phng din ha hc l g? 24. Ti sao c ngi cn gi cc hp cht thm l hp cht phng hng? Cc mi ca cc loi hp cht ny c thm thc s v tt cho sc khe khng? 25. Ti sao benzen khng lm mt mu nu ca nc brom, cng nh khng lm mt mu tm ca dung dch KMnO4, trong khi hexen-2 th lm mt mu d dng hai dung dch trn? Cng nh toluen lm mt mu tm ca dung dch KMnO4?