14352986 7 preparacion de ciclohexeno

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  • 8/12/2019 14352986 7 Preparacion de Ciclohexeno

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    UNIVERSIDAD DEL VALLE DE MXICOCAMPUS CHAPULTEPEC

    LABORATORIO DE QUMICA ORGNICA II

    PRCTICA # 7

    PREPARACIN DE CICLOHEXENO

    Q.F.B. IV SEMESTRE

    INFORMACIN

    La rea!" $ara %&'eer !(%)e*e% a $ar'!r +e !(%)e*a%( e, re-er,!&(e. La re-er,!&!(!+a+ +e /a rea!" ,e $/e+e e-!'ar0o S! ,e e(!1!a e( $r%+/'% +e( 1e+!% +e rea!" a 1e+!+a 2/e 3,'a ,/e+e.o S! ,e a/1e'a (a %e'ra!" +e /% % -ar!%, +e (%, rea'!-%,.o S! ,e a/1e'a % +!,1!/4e (a 'e1$era'/ra e e( ,e'!+% 2/e ,e 5a-%re6a (a rea!" +!re'a e'.

    P%r (% 'a'% (a, %+!!%e, e*$er!1e'a(e, e (a, 2/e ,e e5e'8a /a rea!" +e'er1!a (%,re,/('a+%, +e 3,'a e /a'% a a(!+a+ 4 a'!+a+ +e( $r%+/'% %&'e!+%.

    OBJETIVOS

    Pre$arar !(%)e*e% $%r +e,)!+ra'a!" a'a(9'!a +e !(%)e*a%(. C%1$re+er (a !5(/e!a +e 5a'%re, e*$er!1e'a(e, 2/e 1%+!5!a /a rea!" re-er,!&(e.

    1

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    ANTECEDENTES

    Deshidratacin cataltica de alcoholes para obtener alquenos.

    La +e,)!+ra'a!" +e (%, a(%)%(e, e, / 13'%+% %18 +e %&'e!" +e a(2/e%,. La $a(a&ra +e,)!+ra'a!"

    ,!:!5!a (!'era(1e'e ;$3r+!+a +e a:/a.A( a(e'ar (a 1a4%r9a +e (%, a(%)%(e, % / a!+% 5/er'e ,e $r%-%a (a $er+!+a +e /a 1%(3/(a +e a:/a Q/91!a Or:?!a ED. Pear,% E+. K M3*!% JJ $ JJ

    2

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    Reacciones de eliminacin

    Ua e(!1!a!" !1$(!a (a $er+!+a +e +%, ?'%1%, % :r/$%, +e( ,/,'ra'% :eera(1e'e % (a 5%r1a!" +e /e(ae $!. De$e+!e+% +e (%, rea'!-%, 4 +e (a, %+!!%e, e (a, 2/e ,e e/e're /a e(!1!a!" +e&er9a,er / $r%e,% +e $r!1er %r+e

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    La rea!" E '!ee (/:ar % /a e,'ere%2/91!a +e5!!+a0 e( :r/$% ,a(!e'e 4 e( )!+r":e% ,%&re e( ar&%% e$%,!!" %'!:/a )a +e e,'ar e +!,$%,!!" a'!$er!$(aar.

    La e(!1!a!" 'a1&!3 $/e+e ,er &!1%(e/(ar e $re,e!a +e /a &a,e 5/er'e (a -e(%!+a+ +e e,'a e(!1!a!"e, $r%$%r!%a( a (a, %e'ra!%e, 'a'% +e( )a(/r% +e a(2/!(% %1% +e (a &a,e +a+% (/:ar a /a e/a!" +e-e(%!+a+ +e ,e:/+% %r+e. E,'% e, / $r%e,% &!1%(e/(ar 4a 2/e $ar'!!$a e( )a(/r% +e a(2/!(% 4 (a &a,e e e(e,'a+% +e 'ra,!!" $%r (% 2/e e,'e 1ea!,1% ,e e*$re,a %1% E.

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    Reversibilidad e irreversibilidad de una reaccin

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    C/a+% ,e $er1!'e 2/e (%, a(2/e%, rea!%e % a!+% ,/(58r!% %e'ra+% 5r!" (%, e(e1e'%, +e H SO ,ea:re:a a( +%&(e e(ae 4 5%r1a ,/(5a'%, ?!+%, +e a(2/!(% RFOFSOH0

    La rea!" :eera( $ara (a a+!!" +e( a!+% ,/(58r!%0

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    E( !-e,'!:a+%r 2/91!% ,/e(e e1$(ear e,'a rea!" e e( (a&%ra'%r!% $%r ,er /a &/e 5%r1a +e e(!1!ar a (%,a(2/e%, % +e,ea+%,

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    a1&!:/a 4 % ,e $/e+e e1$(ear $ara $re+e!r (a %r!e'a!" +e a+!!" a a(:/%, a(2/e%> P%r ee1$(% (a re:(a+e Mar%-!%- % '%1a e %,!+era!" (a, 'ra,$%,!!%e, 1%(e/(are,.

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    CH2=CH2 + &'nO4H2O

    OH-CH2-CH2

    OH OH

    + 'nO2

    CH3-CH=CH21.-OsO4/ H2O2.- !a2SO3

    CH3-CH-CH2 + OsO3

    OHOH

    0teno rura

    0tenodiol-1/2 etilenlicol%

    reciitado caf oscuro

    roeno

    roenodiol-1/2 roenillicol%

    + &'nO4H2O

    OH OH

    + 'nO2

    CicloentenoCicloentanodiol-1/2 cicloentenlicol%

    E( 1ea!,1% +e (a rea!" +e %*!)!+r!(a!" ,e )a e,'/+!a+% e*'e,a1e'e. La e,'ere%2/91!a +e,e1$ea /!1$%r'a'e $a$e( e (a +!(/!+a!" +e( 1ea!,1%. P%r ee1$(% (a rea!" e're e( !(%$e'e% 4 e($er1a:aa'% +e $%'a,!% 2/e ,%(% $r%+/e e( cisF!(%$e'a%+!%(F.

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    A 1e+!+a 2/e ,e 5%r1a e( !% 1a:ae,%

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    Z C!(%)e*a%( J.J 1( Z !+% ,/(58r!% %. J.K 1(Z S%(. +e MO a( J.\ K1(

    Z S%(. +e NaHCO a( K\ K 1(

    Z S/(5a'% +e ,%+!% a). .J : Z C(%r/r% +e ,%+!% Q.P. .J :

    ACIDO SULFURICO"#ceite de vitriolo: $%&'( )Ma,a 1%(e/(ar0 .ESTADO ISICO> ASPECTO0 L92/!+% )!:r%,"$!% !%(%r% ae!'%,% e !%+%r%.PELIGROS QUIMICOS0 P%r %1&/,'!" 5%r1a!" +e )/1%, '"*!%, +e "*!+%, +e a6/5re. La ,/,'a!a e, /

    %*!+a'e 5/er'e 4 rea!%a -!%(e'a1e'e % 1a'er!a(e, %1&/,'!&(e, 4 re+/'%re,. La ,/,'a!a e, / ?!+%5/er'e rea!%a -!%(e'a1e'e % &a,e, 4 e, %rr%,!-a $ara (a 1a4%r9a +e 1e'a(e, 1?, %1/e, %r!:!a+%)!+r":e% ,! e1&ar:% ,e $/e+e a(a6ar r?$!+a1e'e /a%e'ra!" %!-a +e $ar'9/(a, e e( a!re $%r $/(-er!6a!". La ,/,'a!a e, %rr%,!-a +e (%, %%, (a $!e( 4 e('ra'% re,$!ra'%r!%. C%rr%,!-a $%r !:e,'!". La !)a(a!" +e( aer%,%( +e (a ,/,'a!a $/e+e %r!:!ar e+e1a$/(1%ar . L%, $/(1%e, $/e+e re,/('ar a5e'a+%, $%r (a e*$%,!!" $r%(%:a+a % re$e'!+a a( aer%,%( +e e,'a,/,'a!a. S! (a, e*$%,!!%e, a( aer%,%( +e e,'a ,/,'a!a ,% re$e'!+a, % $r%(%:a+a, e*!,'e e( r!e,:% +e$re,e'ar er%,!%e, +e'a(e,. E,'a ,/,'a!a $/e+e ,er $e(!:r%,a $ara e( a1&!e'e> +e&er9a $re,'ar,e a'e!"e,$e!a( a (%, %r:a!,1%, a/?'!%,.PROPIEDADES SICAS0 P/'% +e e&/((!!" P/'% +e 5/,!"0 J]C> De,!+a+ re(a'!-a S%(/&!(!+a+ e a:/a0 M!,!&(e> Pre,!" +e -a$%r Pa a Y]C0 J.> De,!+a+ re(a'!-a +e -a$%r De,!+a+ re(a'!-a S%(/&!(!+a+ e a:/a :JJ 1( a J]C0 > Pre,!" +e -a$%r Pa a J]C0 J.> De,!+a+ re(a'!-a +e -a$%r De,!+a+ re(a'!-a +e (a 1e6(a -a$%ra!re a J]C P/'% +e !5(a1a!"0 Y]C .. >Te1$era'/ra +e a/'%!:!!"0 JJ]C> L91!'e, +e e*$(%,!-!+a+ \ e -%(/1e e e( a!re0 .F> C%e5!!e'e +ere$ar'% %'a%(a:/a %1% (%: P%@0 .Pr%$!e+a+e, 2/91!a,0 Rea!%a -!%(e'a1e'e % %*!+a'e, 5/er'e,.> A'aa e( $(?,'!%.CLORURO DE HIDROGENO

    "A!+% (%r)9+r!% a)!+r%(%r/r% +e )!+r":e% a)!+r%: HC(>Ma,a 1%(e/(ar0 Y.K:1%(==*ropiedades fsicas: P/'% +e e&/((!!" a J. Pa0 FK]C+ P/'% +e 5/,!"0 F]C+ S%(/&!(!+a+ e a:/a :JJ

    1( a J]C0 7+ S%(/&!(!+a+ e a:/a0 E(e-a+a+ De,!+a+ re(a'!-a +e -a$%r O%,0 C%rr%,!-%. D%(%r -!,!" &%rr%,a2/e1a+/ra, $r%5/+a, :ra-e,.*ropiedades qumicas: La +!,%(/!" e a:/a e, / ?!+% 5/er'e rea!%a -!%(e'a1e'e % &a,e, 4 e,%rr%,!-a. Rea!%a -!%(e'a1e'e % %*!+a'e, 5%r1a+% :a, '"*!% +e (%r%. E %'a'% % e( a!re +e,$re+e)/1%, %rr%,!-%, +e (%r/r% +e )!+r":e%. A'aa a 1/)%, 1e'a(e, 5%r1a+% )!+r":e%CLORURO DE SODIO C%(%r0 !%(%r%> O(%r0 !%(%r%> P/'% +e e&/((!!"0 C+ P/'% +e 5/,!"0 7KK C> L!1!'e +e e*$(%,!"0 &a%> Pre,!" +e -a$%r0 De,%1$%,!!" '3r1!a07KJ C*ropiedades to,icolgicas: Tra, (a !)a(a!" +e $%(-%0 !rr!'a!%e, (e-e,+ Tra, %'a'% % (%, %%,0 (e-e,!rr!'a!%e,+ Tra, !:e,'!"0 a,a!%+ Tra, !:e,'!" e :ra+e, a'!+a+e,0 %5/,!" -%1!'% 4 e,$a,1%,.PERMANGANATO DE POTASIO:MOMa,a 1%(e/(ar0 KEstado fsico:Cr!,'a(e, $8r$/ra %,/r%*eligros qumicos:La ,/,'a!a ,e +e,%1$%e a( a(e'ar(a !'e,a1e'e $r%+/!e+% :a,e, '"*!%, 4 )/1%,!rr!'a'e,. La ,/,'a!a e, / %*!+a'e 5/er'e 4 rea!%a % 1a'er!a(e, %1&/,'!&(e, 4 re+/'%re, a/,a+%$e(!:r% +e !e+!% % e*$(%,!". Rea!%a -!%(e'a1e'e % 1e'a(e, e 5%r1a +e $%(-% %r!:!a+% $e(!:r% +e!e+!%.-o,icidad: La ,/,'a!a e, %rr%,!-a $ara (%, %%, (a $!e( 4 e( 'ra'% re,$!ra'%r!%. C%rr%,!-a $%r !:e,'!". La!)a(a!" +e( $%(-% +e e,'a ,/,'a!a $/e+e %r!:!ar e+e1a $/(1%ar. L%, e5e'%, $/e+e a$areer +e 5%r1a %!1e+!a'a. Se re%1!e+a -!:!(a!a 13+!a.*ropiedades fsicas:Se +e,%1$%e $%r +e&a% +e( $/'% +e 5/,!" a J]C> De,!+a+0 .7:1 S%(/&!(!+a+ ea:/a :JJ 1( a J]C0 Y.> Pre,!" +e -a$%r Pa a J]C0 +e,$re!a&(e.

    6

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    SULFATO DE SODIO

    WS/(5a'% ,"+!% Ma,a 1%(e/(ar0 .*ropiedades to,icolgicas: La ,/,'a!a ,e $/e+e a&,%r&er $%r !)a(a!" 4 $%r !:e,'!"0 D%(%ra&+%1!a( +!arrea ?/,ea, -"1!'%,.*ropiedades fsicas:P/'% +e 5/,!"0 ]C; De,!+a+ re(a'!-a

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    = Te:a /!+a+% +e /'!(!6ar e( 1a'er!a( &!e (!1$!% 4 ,e%.= E( $/'% +e e&/((!!" +e( !(%)e*e% e, +e F% C. a 7YJ 11H: 4 %1% (a $re,!" a'1%,53r!a e e( D. e,

    +e K7JFKJ 11H: e( $/'% +e e&/((!!" +e( !(%)e*e% e, +e 7F7C.

    Realice la siguiente prueba de realice la siguiente prueba de instauracin:

    Reaccin con 4n'(.

    o E / '/&% +e e,a4% %(%2/e 1( +e ,%(/!" +e $er1a:aa'% +e $%'a,!%

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    911.4118887)85.8

    83747.8.di:;e9 ==

    mol

    molAienton

    5uadro de los datos e,perimentales de los dos m/todos de obtencin del ciclohe,eno.

    M3'%+%, C%+!!%e,E*$er!1e'a(e,

    Te1$era'/ra+e

    (a +e,'!(a!"

    V%(/1e+e(

    +e,'!(a+% (!1!'a'e +e (a -e(%!+a+=

    O-H

    H

    + H2O

    Pa,% 0 A&,'ra!" +e $r%'"

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    *rueba de instauracin: *rueba de !aeer con permanganato de potasio

    + &'nO4OH

    OH

    + 'nO2

    reciitado caf oscuroCiclo$e

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    DISCUSIN DE RESULTADOS0

    Se rea(!6" (a %&'e!" +e !(%)e*e% a $ar'!r +e !(%)e*a%( $%r 1e+!% +e (a '3!a +e +e,)!+ra'a!" +ea(%)%(e, a'a(!6a+a $%r ?!+%, $%r +e,'!(a!" 5ra!%a+a.

    La rea!" ,e rea(!6" e e( 1a'ra6 +e &%(a a( %'eer !(%)e*a%( e !r a:re:a+% e( ?!+% ,/(58r!% (a rea!" ,!:/!" / 1ea!,1% +ee(!1!a!" /!1%(e/(ar.

    La 'ra1$a 2/e ,e )!6% % $er1a:aa'% +e $%'a,!% 5/e $ara a'ra$ar e( ?!+% 2/e ,e -a$%r!6a&a 4a 2/e e($er1a:aa'% e, / %*!+a'e. Se a(e'" $ara +e,'!(ar e( !(%)e*e% 4 ,e re!&!" a /a 'e1$era'/ra +eYC 2/e e e( $r%e+!1!e'% +e9a 2/e e,'e +e&9a ,er a JFKC $er% a !-e( +e( 1ar 4 4a 2/e e,'a1%, ee( D (a $re,!" e, 1e%r 4a 2/e e,'a1%, a KY 11H: $%r (% 'a'% )a!e+% (a %-er,!" %, +a /a'e1$era'/ra +e e&/((!!" +e( !(%)e*e% +e Y.C $%r (% 2/e +e,'!(% a &/ea 'e1$era'/ra /e,'r%$r%+/'% %&'e!e+% a,9 +e( +e,'!(a+% /a 1e6(a +e !(%)e*e%a:/a 4 e e( re,!+/% +e( 1a'ra6 e( ?!+%,/(58r!% 4 1a'er!a %r:?!a +e:ra+a+a 2/e ,e -e9a +e %(%r e:r% a1ar!((e'%.

    Para ,ear e( $r%+/'% ,e /'!(!6" NaC( 4 ,e +ea'" e( $r%+/'% e e( /?( ,e %&'/-!er% 1( +e ,%(/!"2/e +e,$/3, ,e (a-" % &!ar&%a'% +e ,%+!%> e (a 5a,e a/%,a ,e %&'/-!er% e( NaC( +!,/e('% e e( a:/ae( &!ar&%a'% +e ,%+!% 4 ,/(5a'% +e ,%+!% 5%r1a+%. E (a 5a,e a/%,a ,e 'e9a e( !(%)e*e% !1$/r% 4)81e+% 2/e ,e ,e% % ,/(5a'% +e ,%+!% a)!+r% ,e +ea'" 4 ,e +e,'!(% $%r 1e+!% +e (a '3!a +e

    +e,'!(a!" ,!1$(e a &a% +e a9re $ara %&'eer e( !(%)e*e% $/r% +e( /?( ,e %&'/-!er% 1( 5!a(e, 2/e 5/e(a 1!'a+ +e (% 2/e ,e %&'/-% +e (a +e,'!(a!" 5ra!%a+a $%r (% 2/e ,e ree 2/e (a 1e6(a +e a:/a!(%)e*e% 5%r1a+% era 0.

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    P%r 8('!1% ,e rea(!6" /a $r/e&a +e !,'a/ra!" % $er1a:aa'% +e $%'a,!% a/%,% 2/e e, / %*!+a'e a(rea!%ar % / a(2/e% $r%+/e / $r%+/'% e e( /?( ,e a+!!%a +%, :r/$%, %*!+r!(%, a( +%&(e e(ae5%r1a+% +!%(e,

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    purificar lquidos. &irve para separar de impurezas no voltiles. Esta destilacin debe hacerse lenta perocontinuamente7 de forma que el bulbo del termmetro siempre tenga una gota de lquido condensado8.

    *ero realmente la ms efectiva para nosotros en esta prctica es la destilacin fraccionada que trata de unamezcla de varios lquidos7 es decir la temperatura se va elevando lentamente7 los vapores ascienden por unatorre donde de equilibran con algo de condensacin. Esto auda a que los componentes ms voltiles vaanllegando puros al refrigerante de condensacin. 5ada porcin pura se recoge separadamente9.18

    . F a= `Q/3 e, /a rea!" re-er,!&(e en muchas reacciones la reaccin cesa antes de que se agoten losreactivos. Esto sucede cuando se forman los productos7 reaccionan entre si produciendo los reactivos iniciales unsistema reversible es la evaporacin de un liquido por calentamiento luego condensacin posteriormente porenfriamientoiquido ; calor vapor

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    CONCLUSIONES0

    P%r 1e+!% +e e,'a $r?'!a ,e (%:r" %%er /a '3!a $ara +e,)!+ra'ar a(%)%(e, a'a(9'!a1e'e 'e!e+% e/e'a 2/e (a rea!" rea(!6a+a 5/e /a rea!" re-er,!&(e 4a 2/e ,! % ,e /!+a&a a+e/a+a1e'e (a,%+!!%e, +e 'e1$era'/ra 4 %e'ra!" +e rea'!-%, 4 $r%+/'%, 4a 2/e ,! e,'%, % ,e /!+a (a rea!"$%+r9a re:re,ar,e 4 %&'eer +e /e-% e( rea'!-% %r!:!a( $%r (% 2/e % ,e %&'e+r9a e( $r%+/'% +e,ea+% $%r e,a1!,1a ra6" ,e rea(!6a $r/e&a, %1% (a +e &ae4er

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    o !:r%-e. S.A. ;Q/91!a Or:?!a ED. O*5%r+ e+!!" M3*!% D. P?:,.0 J 77 J.

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