UNIVERSIDAD NACIONAL MAYOR MAYOR DE SAN MARCOS DÉCANA DE AMÉRICA
LABORATORIO DE QUÍMICA ORGÁNICA FACULTAD : INGENIERÍA INDUSTRIAL PREFESOR: QF. LUIS MIGUEL FÉLIX VELIZ. TEMA: HIDROCARBUROS AROMÁTICOS.REACCIONES AROMÁTICOS.REACCIONES DE MONOSUSTITUCIÓN AROMÁTICA.SÍNTESIS DEL NITROBENCENO. GRUPO: VIERNES DE 3- !M. INTEGRANTES:
CÓDIGO:
CARHUALLANQUI CARHUALLA NQUI BASTIDAS" #OSÉ LUIS.
$$$%&&&' $$$ %&&&'
CASTRO LOZANO" CHRISTIAN.
$$$%&$&'
DEL !OZO MARTÍNEZ" EZEQUÍAS MIQUEAS
$$$%&((3
HUACCAN GUTIERREZ" CARLOS ENRIQUE
$$$%&(()
#ORGE MAYO" MAYO" CRISTIAN MIGUEL
$$$%&&(
ORTEGA ALVARADO" *ILDE.
$&$%&$+&
ÍNDICE 1
I.-CARÁTULA Y ÍNDICE,,,,,,,,,,,,,,,,,,,,,,,,,,.!.$-(
II.-INTRODUCCIÓN,,,,,,,,,,,,,,,,,,,,,,,,,,,,.!.3
III.-FUNDAMENTO TEÓRICO,,,,,,,,,,,,,,,,,,,,,,,,!.+-)
IV.-MATERIALES,,,,,,,,,,,,,,,,,,,,,,,,,,,,.,!.%
V.-!ROCEDIMIENTO EX!ERIMETAL /RESULTADO0..........,,,,,,,,,,,!.'-$&
VI.-CUESTIONARIO,,,,,,,,,,,,,,,,,,,,,,,,,,,,!.$$-$(
VII.-CONCLUSIONES,,,,,,,,,,,,,,,,,,,,,,,,,,..,!.$3
VIII.-RECOMENDACIONES,,,,,,,,,,,,,,,,,,,,,,..,.,!.$+
IX.-BIBLIOGRAFÍA,,,,,,,,,,,,,,,,,,,,,,,,,,,......!.$
II.-INTRODUCCIÓN: A 124567158 9 ;1527<;2= 67 ><? 54<2@61158 @ 97 5;2<47157 @ 97 =4=5= @9 54<2>12.
2
E9 54<2>12 = 2>45 2< 54<7158 @ >12 12 67 ;197 @ 15@2 4<512 15@2 =69<512" @2;57@7 ;197 =6924<517. R71152= C2 <@6142<= 6<4= 12;2 9 5@<82 =4746= 715@5 /7 97 2<7 @ 2<;7<=0 9 54<2>12 = <@615@2 7 97 75957. L7 <@61158 @9 54<2>12 12 5<<2 15@2 192<@<512 <7 9 ;42@2 ;= 645957@2 7<7 2>4< =47 7;577<2;4517. E <71152= @ =6=4546158 914<29517 =2>< 9 =5=4;7 7<2;4512 9 <62 54<2 >7J7 97 <7145?5@7@ @5<5 9 <62 4<74 2=5158 ;47. A9517152= E9 54<2>12 = 6 12;6=42 @ 7<45@7 5;2<474 97 =4=5= @ @5?<=2= <2@6142= 2<512= 12;2 97 75957" 97 >5@57" 9 4<554<2>12" 9 15@2 54<2>29=698512" 97 61=57" 97 K652957 2 <;712= 12;2 9 71427;522. A ?1= = 645957 47;>5 12;2 @5=29?4" 12;2 12;24 @ 96><5174= 2 12;2 7@545?2 92=5?2=. A4567;4 = 645957>7 47;>5 12 9 2;>< @ A154 @ ;5<>77 2<;697152= @ <6;=. H2 =47= 79517152= =4 <25>5@7= @>5@2 7 97 9?7@7 42515@7@ 9 95<2 K6 =62 7<7 9 ;@52 7;>54. A<25;7@7;4 9 @9 54<2>12 = 645957 7<7 97 <2@61158 @ 75957" 12;2 <16<=2< @9 17612 =544512 97 97>2<7158 @ =4515@7= " 1292<74=" 92=5?2= <2@6142= 7<;7164512=. B52K6;517 42512927 E9 54<2>12 6@ =< <=2<>5@2 7 4<7?= @ 97 59" 92= 69;2= 2 4<7= 5=458 2< 9 54=452. E 9 16<2 <2?217 <7?= 542517152=. E <5;<7 5=47157 <711527 12 97 ;292>57 @ 97 =7< 2<;7@2 ;47;292>57. A@;= <2?217 <7?= @72= 9 =5=4;7 595@7@" @292< @ 17>7" 1797;><=" ?8;542= <@5@7 @ 1215157. U7 542517158 <7? 6@ <2?217< 97 ;6<4 16=458 @ 2<7=. E9 142 48512 = ? <2<47915@2 2< 9 791229.
III.-FUNDAMENTO TEÓRICO:
3
HIDROCARBURO AROMÁTICO M291697 @ benceno" 9 12;6=42 7<2;4512 ;= <12215@2. U 5@<217<>6<2 7<2;4512 = 6 polímero cíclico 12J67@2 K6
16;9
97 Regla de Hückel" = @15<" K6 45 6 42479 @ +P( electrones pi 9 anillo. !7<7 K6 = @ 97 aromaticidad " @> 16;95<= 15<47= <;5=7=" 2< J;92
K6 92=
@2>9= 971= <=274= @ 97 molécula =4 conjugados
K6 =
@ 79 ;2= @2= 2<;7= resonantes K65?794=. L7 =47>595@7@ 115279 @ =42= 12;6=42= 97 9517158 @ 97 <97 @ H19 7 =5@2 9517@7= cuánticamente" ;@574 9 ;2@92 @ 7<41697 6 75992 O<5579;4 9 4<;52 =47>7 <=4<55@2 7 6 <2@6142 @9 alquitrán mineral" 9 benceno" 7 =6= @<5?7@2=" <2 97 7146795@7@ 5196 17=5 97 ;547@ @ 42@2= 92= 12;6=42= 2<512= 9 <=42 =2 92= 997;7@2= compuestos alifáticos. E9 ;5;2 24 @ 97 7;5957 @ 92= 5@<217<>6<2= 7<2;4512= = 9 benceno /C)H)0" <2 5=4 24<2= J;92=" 12;2 97 7;5957 @ anulenos" hidrocarburos ;22119512= 42479;4 12J67@2= @ 8<;697 <79 /CH0. ESTRUCTURA U7 17<714<=4517 @ 92= 5@<217<>6<2= 7<2;4512= 12;2 9 >12" 74<52<;4 ;1527@7" = 97 12977<5@7@ @9 75992 2 97 47;>5 997;7@7 <=27157" @>5@7 7 97 =4<6146<7 914<8517 @ 97 ;291697. A9 @5>6J7< 9 75992 @9 >12 = 9 2 4<= 971= @2>9= 4<= 971= =5;9=. D4<2 @9 75992 2 5=4 <795@7@ @2>9= 971= 12J67@2= <=274=" =52 K6 97 ;291697 = 67 ;197 =5;6947 @ 42@7= 97= =4<6146<7=" K6 124<5>6 2< 5679 7 97 =4<6146<7 914<8517. E 9 >12" 2< J;92" 97 @5=47157 54<748;517 C-C =4 4< 97 @ 6 971 /=5;70 =5;9 97 @ 62 /50 /@2>90. T2@2= 92= @<5?7@2= @9 >12" =5;< K6 = ;747 547142 9 75992" = 12=5@<7 7<2;4512=. L7 7<2;74515@7@ 6@ 5196=2 4@<= 7 =5=4;7= 295119512=" 12;2 9 74792" 74<712" 74<2 24<2= ;= 12;9J2=" 5196=2 15<42= 17452= 752=" 12;2 9 47@5592" K6 2= 9 ;<2 7@167@2 @ 914<2= K6 7@;= =2 1771= @ 1<7< 2<;7= <=274=.
E=4<6146<79;4" @4<2 @9 75992 92= 42;2= @ 17<>22 =4 65@2= 2< 6 971 =( 4< 992= 12 92= @ 5@<82" K6@7@2 6 2<>5479 <@51697< 79 972 @9 75992 K6 2<;7 12 9 <=42 @ orbitales @ 92= 24<2= 42;2= 6 orbital 2< 15;7 2< @>7J2 @9 75992.
DERIVADOS DEL BENCENO MONOSUSTITUIDOS S2 12;6=42= @2@ 62 @ 92= 5@<82= @9 >12 7 =5@2 =6=45465@2 2< 6 42;2 @ 24<2 9;42 2 2< 6 <62 @ 42;2=. S6 =4<6146<7 = 6@ <<=47< 12;2 X S @2;57 2;><7@2 9 =6=45464 7 124567158 97 797><7 >12" 12;2 192<2 >12 /X C90 54<2>12 /NO( -0. !7<7 7962=" = <164 9 6=2 @ 92= 2;><= 12;6= 12;2 42962 2 ;459 >12" 29 2 5@<25 >12 75957 2 7;52 >12. L7 75957 2;><7@7 12;2 67 7;57 7<2;4517 = @2;57 59 7;57" =5@2 9 59 9 <7@5179 K6 = @<5?7 @9 >12 79 95;57<9 6 5@<82. L2= <7@5179= @<5?7@2= @ 92= 5@<217<>6<2= 7<2;4512= = @2;57 <7@5179= 7<592=. !<25@7@= K6;517= @9 >12: E9 >12 @7 12 71595@7@ <71152= @ =6=4546158: $- N54<7158:
REACCIONES Q6;517;4" 92= 5@<217<>6<2= 7<2;4512= =2 12;6=42= 2< <97 <79 >7=474 5<4= 7 97 =6=4546158 914<8597 7 97 5@<27158" <71152= K6 @> 99?7<= 7 17>2 12 76@7 @ catali!adores . E=47 =47>595@7@ = @>5@7 7 97 <=157 @ 2<>5479= @<7@2= /12;7<7@2 =47= ;291697= 12 =6= 7922= 7954512=0 K6 1299?7 67 @5=;56158 <79 @ 97 <7 42479 @ 97 ;291697. "ustituci#n electrofílica /97 94<7 <57 W = 6=7 7<7 @=57< 9 75992 590:
W-H P HNO3 W-NO( P H(O W-H P H(SO+ W-SO3H P H(O W-H P B<( P F W-B< P HB< P F Reacci#n $riedel%&rafts" 24<2 452 @ =6=4546158 914<29517: '
W-H P RC9 P A9C93 W-R P HC9 P A9C93 NITRACIÓN DEL BENCENO: R71158 @ ;22=6=4546158. E =4 17=2" 9 15@2 4<512" =892" 2 ;197@2 12 15@2 =69<512 /;197 =6924<517" 2<;7@7 2< 4<= 7<4= @ ácido sulf(rico 2< 67 7<4 @ 15@2 4<5120" @7 12;2 <=6947@2 97 2>4158 @ <2@6142= @<5?7@2= 54<7@2= 2< =6=4546158. E9 =69<512 12 9 767 K6 = <2@61 97 54<7158" 7>=2<>5@297 6= 45 9 79 @ 6<4 @=5@<7474" ?547@2 97 <2@61158 @ 67 <71158 5?<=7. L7 ;197 =6924<517 <711527 12 9 >12 7 67 4;<746<7 42<2 7 92= &-)&C. A ;72< 4;<746<7 = <2@615< 67 @5=6=4546158. C)H) P HONO( / H(SO+0 C)H NO( /54<2>120 P H (O M175=;2 @ 97 54<7158 E9 52 54<252 NO(P = 9 914<8592 K6 74717 79 >12" =5 ;>7<2 97 1/NO(P0 9 15@2 4<512 = @;7=57@2 >7J7 7<7 54<7< 79 >12 7 67 ?9215@7@ 12?54" <2 77@5@2 H(SO+ 79 HNO3 97 1214<7158 @ 54<252 76;47.
VI.-MATERIALES:
TUBOS DE ENSAYO GRADILLA HNO3 /1214<7@20 H(SO+ /1214<7@20 BENCENO LA!IZ REGLA )
CAMARA DE REVELADO SILICAGEL MECHERO CA!ILARES
V.-!ROCEDIMIENTO EX!ERIMETAL /RESULTADOS0: E =47 <14517 @ 97>2<742<52 ;2= =54457@2 9 54<2>12 12;7;2= @ 97 =5654 ;7<7: !<5;<2 = ?5<4 6 46>2 @ =72 &.;L @ 15@2 4<512" 962 @ 992 = 9 7<7 &.;9 @ 15@2 =69<512 62= 16742= ;5642= = ?69? 7<7< 97 ;5=;7 1745@7@ @ 15@2 =69<512" 79 ;197<= 9 46>2 @ =72 = 6@ 2>=12 72<7 = 6@2 2>=7 197<7;4 97 2<;7158 @ @2= 7== @ 1292< 7;7<5992 97 24<7 7= @ 1292< 7<7J7" 197<2 =4 K6 79 7=7< 62= ;5642= = =47>7 2<;7@2 9 54<2>12 <7157= 7 97 7547158 K6 = 9 717 79 46>2 @ =72" 97 7<4 =6<52< =47>7 9 54<2>12 @ 1292< 7;7<5992 197<2 4@5@2 7 =< 4<7=7<4. A= = <7958 97 =4=5= @9 54<2>12. S6@2 = 52 97 1<2;742<77 7<7 ?< K6 47 6<2 <7 97 2>4158 @ 6=4<2 54<2>12. !7<7 992 = =5658 92= =5654= 7=2=: !<5;<2 = ;5@58 97= @5;=52= =2>< 97 47>947 2 1<22<7;7 7 &.1; 92= @2= 642= @2@ = 17<7 97 ;6=4<7 <2>9;7 97 ;6=4<7 K6;517;4 6<7 7 97 7<4 =6<52< = ;5@ $1; = 71 67 97. S6@2 @=6= @ 7>< 12 9 <5;< 7=2 =65;2= 7 2>4< 6 17597< 7<7 992 = 9 179547 =2>< 6 ;1<2 = 2 97 7<4 14<79 =2>< 9 62 = =45<7 12 165@7@2 7= = 2>45 9 17597< 12 9 1679 = 645957<7 9 =5654 7=2. *
T<1<2 = 18 62 @ 92= 642= 24547= @ 97 ;6=4<7 K6;517;4 6<7 12 6 17597< 2>45@2 9 =6@2 7=2 <2 @ ;7<7 K6 79 79517< 67 247 = =<7 K6 = =K6 <15 = 9 17 97 24<7 247 7= =61=5?7;4 7=47 12;947< 97= 247=" 962 = <21@ 7 17< 97 ;6=4<7 <2>9;7. D 5679 ;7<7 K6 9 74<52< = 18 12 6 17597< 247= @ 97 ;6=4<7 <2>9;7" 962 @ 12;947< 42@7= 97= 247= = =<7 K6 =K6 97 9717 7<7 =65< 962 9 =5654 7=8. C67<42 962 @ K6 = 77 =17@2 97 9717 = <21@ 7 4<7=97@7<92 7 97 1;7<7 @ =746<7158 12 ;612 165@7@2" 962 =<7< 7=47 K6 9 =29?4 />12 9 714742 @ 45920 167@2 =4 2< 997< 7 97 97 K6 = 7>7 ;7<17@2 7 $1;. L62 <4<792 12 165@7@2 @ 97 1;7<7 @ =746<7158 @J7<92 =17<.
Q6542 72<7 = <21@ 7 4<7=97@7<92 7 97 1;7<7 @ <?97@2 @2@ = 7< 6=2 @ 92= ?72<= @ Y2@2 7 = 2>4@< 9 <12<<5@2 K6 71 97 ;6=4<7 <2>9;7 97 ;6=4<7 K6;517;4 6<7" 962 @ 62= ;5642= = <21@ 7 <45<7<92. S42 72<7 = 71 9 795=5= = 7997<7 9 RF /R97158 @ 96J20 12 97 <97158 @9 <4 @ =29642 12 9 <4 @9 =29?4 24<7= 797><7= = ?< 6 97 717 @ C7@7 67 @ 97= ;6=4<7= 7 =7 @9 ;6=4<7 <2>9;7 2 @ 97 ;6=4<7 K6;517;4 6<7. S 71 97= ;@5152= 12<<=2@54=. E 6=4<2 17=2 = ?58 K6 = = 6@2 2>4< 9 54<2>12 12@5152= 6<7=.
Imágenes del !"#ed$m$en%"&
S 7<7 9 HNO 3 H(SO+ +
S 9 7<7 9 >12
L7 =4=5= @9 54<2>12
C7947@2 9 54<2>12 9 >792 ;7<7
,
R7957@2 97 1<2;742<77 7 @9 54<2>12
VI.-CUESTIONARIO:
'()C*m" s$n%e%$+,!-, l, (n$%!",#e%,n$l$d,. E 9 795=5= = ? 12;2 = 2@<7 2<;7< 97 -54<27147595@7 7 7<45< @9 >12 E 97 =4=5= = =56 9 ;5=;2 ;175=;2 7<7 97 2<;7158 @9 54<2>12 7 7<45< @9 15@2 =69<512" 15@2 4<512 9 >12. L62 9 54<2>12 = 2 67 =296158 @ =472 15@2 192<@<512 7<7 7= 2<;7< 97 75957. Y7 2<;7@2 =4" = 9 7<7 15@2 714512 971579 7<7 @=6= 79 <2@6142 =6;7<9 15@2 =69<512 15@2 4<512" 7;>2= 1214<7@2=. T< 1647 K6 9 15@2 =69<512 15@2 4<512 54
/(In0es%$g1e !e2e!en%e , "%!,s !e,##$"nes 31-m$#,s de #,!,#%e!$+,#$*n de 4$d!"#,!51!"s ,!"má%$#"s& 1-
L2= 5@<217<>6<2= 7<2;4512= =2 12;6=42= 2< 92 <79 >7=474 5<4= 7 97 =6=4546158 914<29517 61929517" <71152= K6 @> 99?7<= 7 17>2 12 76@7 @ catali!adores . E=47 =47>595@7@ = @>5@7 7 97 <=157 @ 2<>5479= @<7@2= /12;7<7@2 =47= ;291697= 12 =6= 7922= 7954512=0 K6 1299?7 67 @5=;56158 <79 @ 97 <7 42479 @ 97 ;291697.
SUSTITUCION ELECTROFILICA AROMATICA A =7< @ K6 92= 914<2= 5 @9 >12 = 164<7 6 =5=4;7 7<2;4512 =47>9" =4 @5=25>9= 7<7 74717< 7 6 914<8592 6<4 @7< 967< 7 6 17<>217458. E=4 17<>217458 =47>5957@2 2< <=27157 = @2;57 12;9J2 =5;7 @>5@2 7 K6 9 914<8592 = 6 79 75992 @9 >12 ;@574 6 6?2 971 =5;7.
L7 <71158 = @24<;517 212 5<@ 7<2;74515@7@ 167@2 74717 7 6 914<8592. L7 7<2;74515@7@ = ?69? 7 <16<7< ;@574 97 <@5@7 @ 6 <248. L7 <71158 92>79 9 2;>< @ =6=4546158 914<29517 7<2;4517. U2 @ 92= 17=2= 6@ =< 9 @ 97 BROMACION DEL BENCENO L7 ><2;7158 =56 9 ;175=;2 <79 @ 97 =6=4546158 7<2;4517 914<29517. E9 ><2;2 2 = =65154;4 914<29512 7<7 <711527< 12 9 >12" <2 6 15@2 @ L5= 6<4" 12;2 9 FB<3" E9 <5;< 7=2 @9 ;175=;2 = 97 2<;7158 @ 6 914<8592 ;= 6<4. E9 1747957@2< <711527 12 9 B<( 7<7 2<;7< 6 914<8592 6<4. E9 747K6 @9 >12 9 914<8592 97 <@5@7 @ <242= @7 ><2;2 >12 12;2 <2@6142 ;72<547<52 1747957 97 <71158. !7=2 $: L7 2<;7158 @ 6 914<8592 ;7= 6<4
!7=2 (: A47K6 914<259512 2<;7158 @9 12;9J2 =5;7
11
!7=2 3: L7 <@5@7 @ 6 <248 @7 967< 7 92= <2@6142=
VII.-CONCLUSIONES:
12
VIII.-RECOMENDACIONES: !7<7 2>4< 62= <=6947@2= ;= 7142=" 7 K6 4< ;= 1647 92= =5654= 7<;4<2=: $. U >6 =7152 9 967< @ 4<7>7J2 67 >67 2<757158 @ 9" = @15< >67 6>517158 @ 92= <7145?2= ;74<579= 12 92= 1679= ?7;2= 7 4<7>7J7<. (. B6=17< 97= 12@5152= 5@79= 7 97 2<7 @ <7957< 97 <14517 / 4;<746<7" 6;@7@" <=58" 41.0. 3. !2=< 92= <7145?2= 1=7<52= /12;942=0" 7<7 ;J2< 12215;542 ;J2< @5?<=5@7@ @ <21@5;542= <=6947@2=. +. U7 >67 95;57 2< 7<4 @ 92= ;74<579=" 7947 6<7 /15@2 =69<512 15@2 4<5120 2< 7<4 @ 92= <7145?2=" 7<7 7= 2>4< <=6947@2= <15=2=. . T< 165@7@2 167@2 = ;75697 92= 15@2= 6<4= 1214<7@2=" 25 9 6=2 @9 >12 7 K6 79 =< ?29459 51292<2 2@<7 176=7< @72. S <12;5@7 6=7< 674= @=17>9= ;7=17<5997. ). D>5@2 7 K6 9 >12 = 212 =296>9 97 ;197 @9 15@2 =69<512 12 15@2 4<512 = <K65< 67 7547158 ?52<2=7. D =47 @@ 9 542 @ 97 <71158. %. E 9 17=2 @ 6=7< 9 4<;8;4<2" =4 @> =47< 1247142 12 97 ;197 @ <71158. '. S @> 7<7< 9 >12 7 97 ;197 @ 15@2 =69<512 12 15@2 4<512 2<152= K67= 12;2 = 5@517 9 <21@5;542. . E9 542 @9 <5;42 @@ @ 97 7547158. T< 1647 K6 9 75992 @ 1292< 77<7J7@2 2<;7@2 97 <71158 = =292 67 ;69=5517152. $&. T<747< @ ;717<= 92 ;2= 2=5>9 12 9 1292< 7;7<5992 @9 54<2>12 7 K6 =4 = <2@6142 @ 67 <71158 24<;517 2@<7 5<<547< 97= ;72= =5 2 = 6=7 92= 674=. $$. M74< 97 4;<746<7 4< 92= & )& <7@2= 14<7@2= 7 K6 =5 97 4;<746<7 = 9?7 =61@<7 67 @5=6=4546152. 13
$(. S <12;5@7 4< 6 12142 197<2 @ 92 K6 =2 92= 5@<217<>6<2= 7<2;4512= =6= <71152= @ ;22=6=4546158. $3. S5 = 1=7<52 6=7< 9 592 K6 = <12;5@7 197= 7<7 <57< ;74< 97 <71158 7 97 4;<746<7 @ & )& <7@2= 14<7@2=.
IX.-BIBLIOGRAFÍA:
Q6;517 O<517 I . M2<<5=2 Q6;517 O<517. C7< Q6;517 O<517. C7<@ /@554790 44:[[=.55@57.2<[55[ B5>952417 @ 12=6947 ENCARTA (&& 44:[[7<;7.K>.6;51.;[16
Q6;517 $$2 - E@617< J6952 1=7< 2?@7.
Q6;517 2<517 >=517" @542<579 B@264. R=4<2 F7>52 .V7<7= L29. R=4<2 #75<2.
44:[[.792=22<;697.12;[
44:[[.6<.=[\K652<@[
1
