bai 46 benzen va alkylbenzen lop 11 nang cao

Chng 7: hirocacbon thmngun hirocacbon thin nhinKhi phn t ch c mt vng benzen th c gi l aren n vng Hirocacbon thm(aren) l nhng hirocacbon trong phn t c cha mt hay nhiu vng benzen.

Khi phn t c nhiu vng benzen th c gi l aren a vng

GVHD: NG TH BCH THUGSTG: HUNH VN TS GIO DC V O TO TP. CN THTRNG TRUNG HC PH THNG NGUYN VIT HNG

128.cdx

129.cdx

130.cdx

131.cdx

BI 46: BENZEN V ANKYLBENZENI CAU TRUC , ONG ANG , ONG PHAN VA DANH PHAP :1 - Cau truc cua phan t benzen : a/ S hnh thanh lien ket trong phan t benzen Hay mo ta s hnh thanh lien ket trong phan t bezen ? Trang thai lai hoa cua Cacbon? S xen phu cac AO ,hnh thanh lien ket ?

2s2p- Nguyen t C trang thai lai hoa sp2 .Moi C s dung 3 AO lai hoa e tao lien ket vi 2 nguyen t C ben canh no va mot nguyen t H Sau AO p con lai cua 6 nguyen t C xen phu ben vi nhau tao thanh AO chung cho ca vong ,tao he lien hp thm ben vng .

BI 46: BENZEN V ANKYLBENZENI CAU TRUC , ONG ANG , ONG PHAN VA DANH PHAP :1 - Cau truc cua phan t benzen : a/ S hnh thanh lien ket trong phan t benzen - Nguyen t C trang thai lai hoa sp2 .- Sau AO p con lai cua 6 nguyen t C xen phu ben vi nhau tao thanh AO chung cho ca vong ,tao he lien hp thm ben vng .- Moi C s dung 3 AO lai hoa e tao lien ket vi 2 nguyen t C ben canh no va mot nguyen t H

b/ Mo hnh phan t :Mo hnh rongMo hnh ac - Phan t benzen co hnh luc giac eu - Cac nguyen t nam trong mot mat phang cac goc hoa tr eu bang 1200 .

c/ Bieu dien cau tao cua benzen : 2- ong ang ,ong phan va danh phap :a/ ong ang :- Khi thay cac nguyen t hiro trong phan t benzen bang cac nhom ankyl , ta c nhom ankylbenzen , hp thanh mot day ong ang cua benzen : CnH2n-6 (n 6)C6H5CH3 C6H5CH2CH2CH3 C6H5CH2CH3

b/ ong phan va danh phap :2- ong ang ,ong phan va danh phap :a/ ong ang :Viet cac CTCT cua C6H5CH2CH3? - Ankylbenzen co ong phan mach cacbon va ong phan v tr nhom the tren vong benzen .Goi ten : So ch v tr + ten nhanh + benzen . V tr cac nguyen t C cua vong goi bang ch so hoac cac ch cai ;[1-2;1-6 goi la ortho (o)],[1-3 ,1-5 goi la meta (m)]; [1-4 goi la para (p).

etylbenzen 1,2-imetylbenzen o - imetylbenzen (0 xilen ) 1,4 imetyl benzen p- imetylbenzen (p- xilen) 1,3 imetylbenzen m imetylbenzen (m xilen )Metyl benzen (toluen)

70.txt$c4d$1342Chemistry-4D-Draw 300Region 0.000 0.000 1342.920 -1620.547#START SETTINGS#Name=Document#DefaultTextFont=Times New Roman; 12 0 R WIN 0 1 18#DefaultLabelFont=Arial; 12 0 R WIN 0 1 18#CurrentColor=0,0,0#BackgroundColor=255,255,255#LineWidth=10.000000#BondLength=375.000000#PaintBrush=1#DashedLineInterval=0.028500#ArrowHeadLength=0.140000#ArrowHeadWidth=0.030000#ArrowHeadFixed=0#ArrowSpaceFixed=0#ArrowSpace=0.050000#ArrowSpaceRatio=0.050000#DoubleBondMinSpace=25.000000#DoubleBondSpaceLengthRatio=0.150000#BoldBondSpaceRatio=0.150000#WedgeBondSpaceRatio=0.666667#HashBondSpaceRatio=0.500000#HashSpace=0.050000#END SETTINGS21 2Times New Roman; 12 0 R WIN 0 1 184 2Times New Roman; 14 0 R WIN 0 1 1812 #Group 042.000 -42.444 1175.431 -1578.5470.000 0.000 0.000 0.00012.06 0#version 210MOL 7 7487.59 -1524.49 0.00 1 1 1 C 0 0879.12 -1298.44 0.00 2 1 2 C 0 0879.12 -846.34 0.00 3 1 3 C 0 0487.59 -620.29 0.00 4 1 4 C 0 096.06 -846.34 0.00 5 1 5 C 0 096.06 -1298.44 0.00 6 1 6 C 0 0487.59 -168.19 0.00 7 1 7 C 0 01 2 0 0 0 0 02 3 2 0 0 0 03 4 0 0 0 0 04 5 2 0 0 0 05 6 0 0 0 0 06 1 2 0 0 0 04 7 0 0 0 0 0#pseudo_bond 0#atom_label 17 11 #Group 0403.625 -96.500 1121.375 -294.000420.500 -188.833 0.000 0.00010.00 01 0CH2CH34 2 84 3 4 5 841 487.000 -168.000 1end@End@ Chemistry-4D-Draw

71.txt$c4d$1630Chemistry-4D-Draw 300Region 0.000 0.000 1586.250 -1378.199#START SETTINGS#Name=Document#DefaultTextFont=Times New Roman; 12 0 B WIN 0 1 18#DefaultLabelFont=Arial; 12 0 R WIN 0 1 18#CurrentColor=0,0,0#BackgroundColor=255,255,255#LineWidth=10.000000#BondLength=375.000000#PaintBrush=1#DashedLineInterval=0.028500#ArrowHeadLength=0.140000#ArrowHeadWidth=0.030000#ArrowHeadFixed=0#ArrowSpaceFixed=0#ArrowSpace=0.050000#ArrowSpaceRatio=0.050000#DoubleBondMinSpace=25.000000#DoubleBondSpaceLengthRatio=0.150000#BoldBondSpaceRatio=0.150000#WedgeBondSpaceRatio=0.666667#HashBondSpaceRatio=0.500000#HashSpace=0.050000#END SETTINGS21 2Times New Roman; 12 0 R WIN 0 1 183 2Times New Roman; 12 0 B WIN 0 1 1822 #Group 042.000 -42.300 1419.250 -1336.1990.000 0.000 0.000 0.00010.00 0#version 210MOL 8 894.00 -721.70 0.00 1 1 1 C 0 094.00 -1096.70 0.00 2 1 2 C 0 0418.76 -1284.20 0.00 3 1 3 C 0 0743.52 -1096.70 0.00 4 1 4 C 0 0743.52 -721.70 0.00 5 1 5 C 0 0418.76 -534.20 0.00 6 1 6 C 0 0418.76 -159.20 0.00 7 1 7 C 0 01118.52 -721.70 0.00 8 1 8 C 0 01 2 0 0 0 0 02 3 2 0 0 0 03 4 0 0 0 0 04 5 2 0 0 0 05 6 0 0 0 0 06 1 2 0 0 0 06 7 0 0 0 0 05 8 0 0 0 0 0#pseudo_bond 11 6 0 1 2 2 3 3 4 4 5 5 6 6 1#atom_label 27 01 #Group 0347.750 -94.300 687.250 -269.680362.000 -177.500 0.000 0.00010.00 01 0CH33 2 831 418.000 -159.000 08 01 #Group 01047.750 -656.300 1387.250 -831.6801062.000 -739.500 0.000 0.00010.00 01 0CH33 2 831 1118.000 -721.000 0end1 #Group 0572.000 -839.000 686.000 -1134.000572.000 -937.000 0.000 0.00010.00 01 0

0@End@ Chemistry-4D-Draw

72.txt$c4d$1537Chemistry-4D-Draw 300Region 0.000 0.000 962.520 -1863.380#START SETTINGS#Name=Document#DefaultTextFont=Times New Roman; 12 0 B WIN 0 1 18#DefaultLabelFont=Arial; 12 0 R WIN 0 1 18#CurrentColor=0,0,0#BackgroundColor=255,255,255#LineWidth=10.000000#BondLength=375.000000#PaintBrush=1#DashedLineInterval=0.028500#ArrowHeadLength=0.140000#ArrowHeadWidth=0.030000#ArrowHeadFixed=0#ArrowSpaceFixed=0#ArrowSpace=0.050000#ArrowSpaceRatio=0.050000#DoubleBondMinSpace=25.000000#DoubleBondSpaceLengthRatio=0.150000#BoldBondSpaceRatio=0.150000#WedgeBondSpaceRatio=0.666667#HashBondSpaceRatio=0.500000#HashSpace=0.050000#END SETTINGS21 2Times New Roman; 12 0 R WIN 0 1 182 2Times New Roman; 12 0 B WIN 0 1 1812 #Group 042.000 -42.300 795.520 -1821.6800.000 0.000 0.000 0.00010.00 0#version 210MOL 8 894.00 -721.70 0.00 1 1 1 C 0 094.00 -1096.70 0.00 2 1 2 C 0 0418.76 -1284.20 0.00 3 1 3 C 0 0743.52 -1096.70 0.00 4 1 4 C 0 0743.52 -721.70 0.00 5 1 5 C 0 0418.76 -534.20 0.00 6 1 6 C 0 0418.76 -159.20 0.00 7 1 7 C 0 0418.76 -1659.20 0.00 8 1 8 C 0 01 2 0 0 0 0 02 3 2 0 0 0 03 4 0 0 0 0 04 5 2 0 0 0 05 6 0 0 0 0 06 1 2 0 0 0 06 7 0 0 0 0 03 8 0 0 0 0 0#pseudo_bond 11 6 0 1 2 2 3 3 4 4 5 5 6 6 1#atom_label 27 01 #Group 0347.750 -94.300 687.250 -269.680362.000 -177.500 0.000 0.00010.00 01 0CH32 2 821 418.000 -159.000 08 01 #Group 0347.750 -1594.300 687.250 -1769.680362.000 -1677.500 0.000 0.00010.00 01 0CH32 2 821 418.000 -1659.000 0end@End@ Chemistry-4D-Draw


74.txt$c4d$1903Chemistry-4D-Draw 300Region 0.000 0.000 1593.000 -1497.700#START SETTINGS#Name=Document#DefaultTextFont=Times New Roman; 12 0 R WIN 0 1 18#DefaultLabelFont=Arial; 12 0 R WIN 0 1 18#CurrentColor=0,0,0#BackgroundColor=255,255,255#LineWidth=10.000000#BondLength=375.000000#PaintBrush=1#DashedLineInterval=0.028500#ArrowHeadLength=0.140000#ArrowHeadWidth=0.030000#ArrowHeadFixed=0#ArrowSpaceFixed=0#ArrowSpace=0.050000#ArrowSpaceRatio=0.050000#DoubleBondMinSpace=25.000000#DoubleBondSpaceLengthRatio=0.150000#BoldBondSpaceRatio=0.150000#WedgeBondSpaceRatio=0.666667#HashBondSpaceRatio=0.500000#HashSpace=0.050000#END SETTINGS11 2Times New Roman; 12 0 R WIN 0 1 1872 #Group 0333.000 -42.300 1086.519 -1336.2000.000 0.000 0.000 0.00010.00 0#version 210MOL 7 7385.00 -721.70 0.00 1 1 1 C 0 0385.00 -1096.70 0.00 2 1 2 C 0 0709.76 -1284.20 0.00 3 1 3 C 0 01034.52 -1096.70 0.00 4 1 4 C 0 01034.52 -721.70 0.00 5 1 5 C 0 0709.76 -534.20 0.00 6 1 6 C 0 0709.76 -159.20 0.00 7 1 7 C 0 01 2 0 0 0 0 02 3 2 0 0 0 03 4 0 0 0 0 04 5 2 0 0 0 05 6 0 0 0 0 06 1 2 0 0 0 06 7 0 0 0 0 0#pseudo_bond 11 6 0 1 2 2 3 3 4 4 5 5 6 6 1#atom_label 17 01 #Group 0638.750 -94.300 958.250 -269.680653.000 -177.500 0.000 0.00010.00 01 0CH31 2 811 709.000 -159.000 0end1 #Group 01094.000 -582.700 1426.000 -778.7001125.000 -680.700 0.000 0.00010.00 01 02(o)11 #Group 01052.000 -1009.700 1416.000 -1205.7001083.000 -1107.700 0.000 0.00010.00 01 03(m)11 #Group 0719.000 -373.700 864.000 -569.700750.000 -471.700 0.000 0.00010.00 01 0111 #Group 0656.000 -1259.700 988.000 -1455.700687.000 -1357.700 0.000 0.00010.00 01 04(p)11 #Group 042.000 -1061.700 406.000 -1257.70073.000 -1159.700 0.000 0.00010.00 01 0(m)511 #Group 042.000 -550.700 374.000 -746.70073.000 -648.700 0.000 0.00010.00 01 0(o)61@End@ Chemistry-4D-Draw

1+3 =4 1+5=6

Cac chat trong day ong angbenzen co so cacbon la bao nhieu th co ong phan?

CTPTCTCTTn thng thngTn thay thC6H6BenzenbenzenC7H8toluenmetylbenzenC8H10etylbenzen0-xilen1,2-imetylbenzen(o-imetylbenzen)m-xilen1,3-imetylbenzen(m-imetylbenzen)p-xilen1,4-imetylbenzen(p-imetylbenzen)

CTPTCTCTC6H6C7H8C8H10

89.cdx

90.cdx

91.cdx

93.cdx

94.cdx

95.cdx

Chn p n ng .Cng thc C tn gi l :a. 4,6-ietyl-1,3-metylbenzenb. 2,4-ietyl-1,5-imetylbenzend. 2,4-ietyl-1,5-metylbenzenc. 1,5-metyl-2,4-etylbenzen123456

II TNH CHAT VAT LY :1 Nhiet o nong chay , t0s va khoi lng rieng :

ArenCong thc phan ttnc ,oCts , oCD , g/cm3 (20oC)Benzen C6H65,5800,879Toluen C7H8-95,01110,867EtylbenzenC8H10-95,01360,867o-Xilen C8H10-25,21440,880m-Xilen C8H10-47,91390,864p-Xilen C8H1013,21380,861n-Propylbenzen C9H12-99,51590,862Isopropylbenzen (Cumen) C9H12-96,01520,862

II TNH CHAT VAT LY :1 Nhiet o nong chay , t0s va khoi lng rieng :

- Nhiet o nong chay nhn chung giam dan , co s bat thng p- xilen :o xilen : m xilen .- Nhiet o soi tang dan .- Khoi lng rieng cac aren nho hn 1g/cm3 cac aren nhe hn nc .2 Mau sac,tnh tan va mui :- La nhng chat khong mau , hau nh khong tan trong nc , tan nhieu trong dung moi hu c . ong thi la dung moi hoa tan nhieu chat khac . - eu la chat co mui , nhng co hai cho sc khoe .Thc hin th nghim :1 a. Benzen vo nc Hin tng b. Benzen vo xng Hin tng.2 - a- Iot vo nc Hin tng b- Cho iot vo benzen lc nh ? nhn xt ,kt lun ?

BI 46: BENZEN v ANKYLBENZENI CAU TRUC , ONG ANG , ONG PHAN VA DANH PHAP :1 - Cau truc cua phan t benzen : 2- ong ang ,ong phan va danh phap:II TNH CHAT VAT LY :1 Nhiet o nong chay , t0s va khoi lng rieng :2 - Mau sac,tnh tan va mui :

1. Kt lun no sau y l ng ?Benzen l mt hirocacbon khng no mch vngABCD Benzen, 3 lin kt n v 3 lin kt i c di bng nhau. Benzen v xiclohexan,6 cacbon to thnh mt lc gic u. Benzen, 3 lin kt i ngn hn 3 lin kt n

2. S ng phn hirocacbon thm c cng thc C8H10 l:5ABCD243

3 Vit cng thc cu to ca cc hp cht sau:Etylbezen.ABCp Clotoluen1,3,5 trimetylbenzen


432.cdx

433.cdx

IV- IU CH V NG DNG1. iu ch* Benzen, toluen, xilen: tch ra bng cch chng ct nha than , du m hoc t ankan, xicloankan.* eltylbenzen:

107.cdx

108.cdx

109.cdx

-Vit cng thc cu to v gi tn cc ng phn ankylbenzen C8H10.- Nhn xt v nhit si, khi lng ring ca cc cht trong dy ng ng benzen

etylbenzen 1,2-imetylbenzen o - imetylbenzen (0 xilen ) 1,4 imetyl benzen p- imetylbenzen (p- xilen) 1,3 imetylbenzen m imetylbenzen (m xilen )


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0@End@ Chemistry-4D-Draw



Nhiet o nong chay , t0s va khoi lng rieng :

ArenCong thc phan ttnc ,oCts , oCD , g/cm3 (20oC)Benzen C6H65,5800,879Toluen C7H8-95,01110,867EtylbenzenC8H10-95,01360,867o-Xilen C8H10-25,21440,880m-Xilen C8H10-47,91390,864p-Xilen C8H1013,21380,861n-Propylbenzen C9H12-99,51590,862Isopropylbenzen (Cumen) C9H12-96,01520,862

GVHD: NG TH BCH THUGSTG: HUNH VN TS GIO DC V O TO TP. CN THTRNG TRUNG HC PH THNG NGUYN VIT HNG

534.cdx

535.cdx

536.cdx

537.cdx

IV- TNH CHT HA HCTRUNG TM PHN NG

111.cdx

112.cdx

IV/ TNH CHT HO HC:Cc ng ng ca benzen c tnh cht ca vng benzen v ca cc mch nhnhTh nguyn t H ca vng benzen

- Phn ng vi halogen.1/ Phn ng th.

th nghim benzen phn ng vi brom ha

M hnh phn ng .

+Xt:Bt Fe,to+ Br2 + HBr

538.cdx

539.cdx

Hy hon thnh phng trnh sau?

+Br2Fe, t041%59%O-bromtoluenp-bromtoluen+HBr

+ Br2 +HBrBr-BrBenzylbromua

57.cdx

58.cdx

60.cdx

Khi cho toluen tc dng vi clo iu kin c chiu sng th sn phm to thnh l:o-clotoluenABCDBenzyl cloruam-clotoluenp-clotoluen

+ HNO3() + HO-NO2 Nitrobenzen b. Phn ng nitro ho H2SO4, + H2O

51.cdx

52.cdx

53.cdx

Khi d HNO3.

M t th nghim iu ch nitro benzen

Cho nitrobenzen tc dng vi hn hp HNO3 v H2SO4 theo t l mol 1:1 thu c sn phm l:OrthoinitrobenzenABCDparainitrobenzenMetainitrobenzen1,3,5-trinitrobenzen

Tng t nh phn ng vi Br2 cc ankylbenzen phn ng vi axit nitric s cho sn phn th vo v tr ortho v para.

+HNO3(),H2SO4 c - H2O2-nitrotoluen(o-nitrotoluen)4-nitrotoluen(p-nitrotoluen)

54.cdx

55.cdx

56.cdx

- Quy tc th vng benzen Khi vng benzen c gn sn nhm ankyl (hay cc nhm OH, -NH2, -OCH3, ) phn ng th vo vng s d dng hn v u tin xy ra cc v tr ortho v para. Ngc li, nu vng benzen c sn nhm NO2 (hoc COOH, -CHO, -SO3H, ) phn ng th vo vng s kh hn v u tin xy ra v tr meta.

Khi nhn benzen c hai nhm th.- khi nhm th no y in t mnh hn s nh hng phn ng.

v d:

So snh kh nng nh hng o- ,p-.

-OH > -NH2 >-OR > -H > -Hal > -NO2 >-CN.

i vi halogenua l nhm ht in t nhng vn nh hng o- v p-.

Ti sao li c s nh hng vo nhn benzen nh trn?-khi nhn c nhm y in t:

-S lin hp lm tng mt electron trong nhn benzen c bit l v tr o- v p-

v tr o-, p- c hot ho phn ng xy ra d dng hn so vi benzen

Khi nhn benzen c nhm ht in t:

S lin hp lm gim mt electron trong nhn benzennh hng -m

Ankylbenzen tham gia phn ng th vi brom s u tin th vo:otho;metaABCDotho;paraPara;metaPara

d) C ch phn ng th vng benzenCc tiu phn mang in tch dng to thnh do tc dng ca chng vi xc tc mi l tc nhn tn cng trc tip vo vng benzen.

C ch phn ng nitro ho.

2/ Phn ng cng.a) Cng hiro .+ 3 H2b) Cng clo + 3Cl2hexacloranXiclohexan

61.cdx

62.cdx

63.cdx

64.cdx

3.Phn ng oxi ha .a. Phn ng xi ha khng han ton. iu kin thng benzen v cc ankylbenzenkhng tham gia phn ng vi KMnO4 . Khi c nhit th benzen cng khng phn ng vi KMnO4 nhng cc ankyl benzen th lm mt mu KMnO4+2KMnO4+ 2MnO2+ KOH+ H2OtoKali benzoat

b. Phn ng oxi ha hon tonCnH2n-6 +

+(n-3)H2O nCO2to

Ho cht v du hiu dng phn bit benzen v toluen:Dung dch KMnO4-Mt mu tmABCDDung dch Br2 - Mt mu dung dch Br2Dung dch KMnO4, un nng -Mt mu tmKh oxi C phn ng chy

V. ng dngBenzen: tng hp cht do, cao su, t si, iu ch ra mt s dn xut khcToluen sn xut thuc n TNT.Benzen,toluen, xilen lm dung mi.

BENZENV. ng dng ca Benzen:

96.bin

97.bin

100.bin

Kt lun: Benzen tng i d tham gia phn ng th, kh tham gia phn ng cng v bn vng vi cc cht oxiho. cng l tnh cht ho hc c trng chung cho cc hirocacbon thm nn c gi l tnh thm.

1. Khi cho toluen tc dng vi kh clo ( xc tc Fe, un nng ) vi t l mol 1: 1 ta thu c:Benzyl cloruaABCDO-clo toluen v p-clo toluenm-clo toluen6.6.6

2. Hp cht thm A c cng thc phn t l C8H10. Cho A tc dng vi dung dch KMnO4 to ra mt axit c cu to i xng. A c tn gi nh th no? etylbenzenACBD m-metyltoluen p-metyltolueno-metyltoluen

3.NU QUY LUT TH VNG BENZEN?* Khi vng benzen c sn (hay cc nhm OH, -NH2, -OCH3 ), p th vo vng v u tin v tr .. V .* khi vng benzen c sn (hoc cc nhm COOH, -SO3H ), p th vo vng ..v u tin v tr ..NHM ANKYLD DNG HNORTHOPARANHM NO2KH HNMETA

4. DNG CTCT VIT PTP V GI TN SN PHMBenzen tc dng brom lng c xc tc bt st.ABCToluen tc dng axit nitric c xc tc axit sunfuric c.Etylbenzen tc dng hidro c xc tc Ni, un nng.

Bi tp.Bi 1 :T benzen ,toluen v cc cht v c iu ch : TNT; 2,4,6 tribromtoluen, axit m-brombenzoic, m-nitrotoluen.Bi 2: So snh phn ng th halogen xy ra benzen vi metan.Bi 3: Nhn bit cc hn hp 2 cht sau: benzen v toluen; benzen v stiren; benzen v xiclohexan.

DN DV nh lm bi tp : 6,7,8,9,10 trong sch gio khoa.

bai 46 benzen va alkylbenzen lop 11 nang cao

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