+ Phan ling the
oj Phan ífn)j halogen hoa
• Benzen va cac dong dang ciia benzen khong phan iíng v6i dung djch brom nhung phan iíng d6 dang vdi brom khan khi c6 mat cOa bot sat lam xiic tac
Br
Br^ Fe + HBr
Brombenzen
Toluen tham gia phan ixng brom hoa dang ban va tao ra san phim g6m hai d6ng ph&n : CH, o + B r , , F e - H B r O ^ CO Br Br p-bromtoluen o-bromtoluen
Clui y: Néu kh6ng dung Fe ma chiféu sang (as) thi Br se the nguyfin tijf H d mach nhanh.
H^C-H H.C-Br + Br. >
o o + H B r
h) Phan nitro hoa
• Benzen tac dung voi h6n hop H N O , dac va H2SO4 dam dac tao thiuih nitrobenzen :
H N O ,
o + H O - N O o H2SO4 d
^0 o + H - , 0
nitrobenzen
Nitrobenzen tac dung voi h6n hop axit H N O , b6c khoi va H,S04 dam dSc
d6ng thdi dun nong thi tao thanh m — dinitrobenzen.
NO, N O , Q ) + H O - N O , "^SQ^d, (Qj^ ^ H 2 O
* ^ ^ N 0 2
m- dinitrobenzen
Toluen tham gia phan ung nitro hoa d l dang hon benzen va tao thanh san
pham th6' o vj tri oitho va para :
CH. CH, o H N O , , H 2 S O 4 d o ^ o NO, NO, p- nitrotoluen o- nitrotoluen + H2O 48 Quy t^c th^ tr£n v6ng benzen
Khi trfin vong benzen da c6 sSn nhom ankyl (hay cac nh6m - O H , - N H j ,
-OCH3, ...), phan ung th6' vao vong benzen se d l dang hon va uti tifin thd' vao vi
tri ortho hoac parạ Ngiroc lai, nd'u b vong benzen da c6 sSn nhom - N O j (hoSc cdc nhom - C O O H , - S O , H , - C O O R , . . . ) , phan ung thé vao vong se kho hon va uu ti6n thé vao vj tri metạ
Phan vfng sunfo hoa • ' »•
Dun nong benzen voi H2SO4 dam dac d6ng thori chung cat nu6c ra khoi h6n hop phan ling se thu duoc axit benzensunfonic :
Q H ^ + HOSOjH ) QH5SO3H + H2O
d) Phan itng ankyl hoa
• Benzen tac dung v6i ankyl clorua c6 mat ciia AICI3 khan se cho ankylbenzen (phuong phap tang mach cacbon dị di6u chS'cac đng d i n g cua benzen).
Q H , + C„H3„. , C I ^'"^ > QH5C„H,„,, + H C l
• Co th^ thay th6' dSn xuát halogen bang ancol hoac anken d^ ankyl hoa benzen
C s H , + C H j C H ^ O H — " ^ ^ ^ i ) C6H5CH2CH3 + H2O
C^Hs + C H , = C H , ). Q H s C H o C H ,
N6'u anken la propilen ta se thu ducic san ph^m chinh la cumen C,H6 + C H , = C H - C H , "2^^°^ ) C,H5CH(CH3),
(cumen)
Phan umg cpng
a)
Benzen va cac ankyl benzen kh6ng lam mat mau dung dich brom flhu cac hidrocacbon kh6ng nọ Khi chid'u sang benzen c6ng vdi clo tao thanh C^HeClj.
C, H , + 3CU CeH^Cl,
(hexaclo xiclohexan)
;)CgnsH,
Q H , + 3 H , ! i l . i L ^ Q H , 2
Phan umg oxi hoa
a) Oxi hoa hoan loan \
C„ H 2„-6+ ^Y^O, -> nCO, + (n - 3)H20 •
) Oxi hoa khong hoan toan
• Khac voi etilen va axetilen, benzen kh6ng phan iJng vdi dung djch KMn04. • Toluen va cac đng dang khi dun nong voi dung dich K M n 0 4 (hoac K2Cr207)
se bi oxi hoa 6 mach nhanh (nhom ankyl) tao ra mu6'i va axit hiru cọ Phan iJng nay dimg de nhan bie't toluen.
-> Q H s C O O K + 2Mn024 + K O H + H.O QH5CH3 + 2KMn04
Nhqn xet: Nd'u nh6m ankyl d vong benzen dhi hem nhom -CH3 thi phan ling oxi hoa mach nhanh v3n iru tifin xay ra or vj tri a d6'i vdi vong.
QH,CH2 - ^ C H j R KMNO, > QH5COOK """^ ) QH5COOH 5. Dieu che benzen va aren
+ Chung cat nhua than da va rifominh din mo thu duoc m6t luong 16n benzen, toluen va naphtalen (diing trong c6ng nghidp)
+ Dehidro hoa d6ng vong hexan va heptan thu duoc benzen va toluen
CH,(CH,),CH3 2Z"<^1 > Q H, - ^ 4 H , CH3(CH2).,CH3 s i i i l P - ^ CftHjCHj + 4H2
+ Dehidro hoa xicloankan hoac metyl xicloankan
+ Trime hoa axetilen
SCH, ^ C,H, 6 " 6
+ Ankyl hoa benzen de A\iu chéđng dang ciia benzen Q H , + C H , , , , ,C1 > QH5QH,,,,, + HCl + Cong H2 vao mach nhanh khdng no
C.H5CH = CH, + Ni, t° -» C^HjCH^CHj
CH=CH,
+ Tir benzen va etilen de diau ché etylbenzen
C^H, + CH, = CH, — i i ^ ^ QH5CH2CH3 I I . S T I R E N VA N A P H T A L E N
1. Stiren
+ CS'u tao va tinh chat v$t li
• Stiren (vinylbenzen, phenyletilen) c6 c6ng thirc cáu tao :
• Stiren la chat long kh6ng mau, nhe hon nude va kh6ng tan trong nu6c. t l . = - 3 1 ° C , t ^ = 145°C.
+ Tinh chat hoa hoc
a) Phan ifng cpng
Tuong tu nhu anken, stiren c6 phan ihig c6ng halogen (Q,, Brj), hidrohalogenua (HCl, HBr) vao nhom vinyl.
C6H5CH=CH2 + Br, - » C^HjCBr-CH^Br
C6H,CH=CH, + HCl ^ CeHjCHCl-CHj
r- C H - C H , - C6H5
1, ) Phcin ling trung hcrp
n C H = CH2 "•^"••^
C6H5
polistiren (PS) v
(•) Phan ifng oxi hoa
Giong nhu etilen, stiren lam mat mau dung djch KMn04 va bi oxi hoa 6 nhom
vinyl, con vong benzen vSn gi& nguyen. ' ' " ' ' ' '
3QH5CH = CH. + 2KMn04 + 4 ^ 0 -> BQHjCHCOH) - CHjOH + 2Mn02 + 2KOH
Phan ling tren dung d^ nhan biét stiren. ,