8

3B-2

GUIA DE PRCTICAS
FACULTAD DEFARMACIA Y BIOQUMICA

GUIA DE PRCTICAS QUMICA ORGNICA - II

Autores:
Mg QF QF QF Q F Lu!s M!gue" F#"!$ %e"!& Ro'ert Ar()*+o C,r+e*)s Or!-ue") Ces)r Augusto C)"+er.* R)(os D)*!e" /)0e& +e" P!*o

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Me lo contaron y lo olvide, lo vi y lo entend, lo hice y lo aprend Confucio, filsofo chino (551-479 AC) INTRODUCCIN Actualmente la Qumica O !"nica e#t" $ %&u#amente in'%luc a(a en ca(a &a#e (e la 'i(a m%(e na. )u ante l%# (ie* a +uince a,%# -ltim%# l%# c%n%cimient%# cient&ic%# .an c eci(% tan "$i(amente +ue .a e#ulta(% (i&cil mantene l%# cu #%# (e ciencia# al (a. A cau#a (e +ue la +umica % !"nica a&ecta a nue#t a# 'i(a# (e tanta# mane a#/ ca(a (a m"# !ente nece#ita un c%n%cimient% (e e#ta mate ia c%m% nece#i(a( $ %&e#i%nal. Na(ie $ue(e $ eten(e la $%#e#i0n (e un am$li% c%n%cimient% (el mun(% actual #in c%n%ce al!% la +umica % !"nica/ cu1% e#tu(i%/ $% %t a $a te/ %& ece 'enta2a# -nica# al e#tu(iante. El aut% .an t ata(% (e euni en e#ta 3ua un c%n2unt% (e $ "ctica# en la# cuale# #e a$li+uen la# $ inci$ale# t4cnica# (e ai#lamient%/ $u i&icaci0n 1 ca acte i*aci0n a ca#%# #encill%#/ (e#$u4# #e int %(ucen $ "ctica# #%5 e la eacti'i(a( 1 #nte#i# (e c%m$ue#t%# % !"nic%#/ +ue $e mita al alumn% inicia #e/ c%n el me2% a$ %'ec.amient% $%#i5le/ en la e6$e imentaci0n (e +umica % !"nica c%n en#a1%# e in'e#ti!aci%ne# $ elimina e# (e #u#tancia# (e#c%n%ci(a#. El t a5a2% $ "ctic% (e ca(a alumn% #e " cali&ica(% $% la t4cnica 1 .a5ili(a( (e#a %lla(a#/ $% la c%m$ en#i0n (e l%# $ inci$i%# t ata(%# en la $ "ctica +ue #e "n $ue#t%# en e'i(encia $% $e+ue,%# e6"mene# % ale# % e#c it%#/ +ue ca(a $ %&e#% .a " a #u# alumn%#. El &in $ inci$al (e e#te cu #% (e $ "ctica c%n#i#te en en#e,a al alumn% el a te 1 l%# $ inci$i%# cient&ic%# en l%# +ue #e &un(amenta la Qumica O !"nica. LMF

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!R"C#UCION"$ % T&CNIC#$ D" TR#'#(O "N "L L#'OR#TORIO) El t a5a2% $ "ctic% en Qumica O !"nica e# tant% un a te c%m% una ciencia. 7a $ ime a $ "ctica e#t" (e(ica(a e#$ecialmente al c%n%cimient% (e la# $ ecauci%ne# 1 t4cnica# (e t a5a2% en el la5% at% i%. 8%(%# l%# la5% at% i%# +umic%# (%n(e el t a5a2% e# & ecuente .an #i(% e#cena i% (e acci(ente#/ la ma1% a (e $%ca im$% tancia/ $e % al!un%# (e ! a'e# c%n#ecuencia#. E#t%#/ a# llama(%# 9acci(ente#: n% #uce(en/ #in% +ue #%n cau#a(%# $% (e#cui(%# % &alta (e atenci0n en el t a5a2%. En el la5% at% i% #e (e5e t a5a2a c%n una mente a5ie ta e in+ui#iti'a/ an%tan(% en#e!ui(a n% l% +ue #e #u$%ne +ue 'a a #uce(e / #in% l% +ue ealmente #e %5#e 'a. ;ient a# #e e#t4 t a5a2an(%/ #e (e5e (e i t atan(% (e inte $ eta t%(% l% +ue #e %5#e 'a/ 1 #i (e#$u4# (e (ete mina(% e#&ue *% n% #e #a5e la e#$ue#ta a al!una cue#ti0n/ n% #e (e5e (u(a en .ace le la c%n#ulta al $ %&e#% . Un cum$limient% i!u %#% (e la# $ ecauci%ne# +ue #e in(ican a c%ntinuaci0n $ e'en( " (i ectamente la ma1% a (e (ic.%# acci(ente# 1 a1u(a " in(i ectamente a l%# alumn%# a a(+ui i a+uell%# ."5it%# (e #e!u i(a( +ue le# #e "n (e ine#tima5le 'al% n% #0l% en el la5% at% i%/ #in% en cual+uie #iti%. 7a# #i!uiente# $ ecauci%ne# 1 n% ma# (e #e!u i(a( #e $ue(en e'ita muc.%# acci(ente#< =. E# %5li!at% i% u#a man(il % 5ata (e la5% at% i% >5lanc% (e al!%(0n? (i#e,a(a $a a $ %te!e la %$a 1 $iel (e #u#tancia# +umica# +ue $ue(an (e ama #e % $ %(uci #al$ica(u a#. )e5e lle'a #e a5 %c.a(a 1 cu5 i .a#ta la %(illa. )e5e #e (e man!a la !a. NO (e5e #u#titui a la cami#a 1@% 5lu#a. 2. Camina n% c% e en el la5% at% i%. 3. El ca5ell% la !% #uelt% $ue(e #e $eli! %#%/ t a5a2a c%n el $el% ec%!i(%. A. N% in!e i aliment%# 1 5e5i(a# $a a e'ita en'enenamient% $% in!e#ti0n. B. N% &uma . C. E'ita la# 'i#ita# $% +ue l% (i#t aen. 7. D% nin!-n c%nce$t% a5an(%na "n el lu!a (e t a5a2% .a#ta .a5e te mina(% la $ "ctica. 8. El lu!a % me#a (e t a5a2% (e5e e#ta % !ani*a(% 1 lim$i% >n% m%c.ila# #%5 e la me#a? E. Reali*a el e6$e iment% una 'e* +ue e#t"# #e!u % (el $lan a #e!ui 1 +ue el $ %&e#% e#$%n#a5le l% aut% ice. =0. El mate ial 5ien lim$i% e# e#encial $a a un 5uen t a5a2%. ==. U#a ma#ca illa $a a t a5a2a c%n #u#tancia# t06ica#/ '%l"tile# % utili*a la# cam$ana# e6t act% a# (e !a#e#. =2. 7ee la eti+ueta (e l%# & a#c%# eacti'%# ante# (e u#a l%#. =3. N% $ %5a l%# eacti'%#. =A. E'ita me*cla l%# eacti'%# #im$lemente $% cu i%#i(a(. =B. ;ani$ula l%# eacti'%# #0li(%# c%n e#$"tula#. =C. N% #e utili*a "n la# $i$eta# #in +ue e#t4n $ %'i#ta# (e la $e a (e .ule a$ %$ia(a/ a n% #e +ue #e t ate #im$lemente (e me(i '%l-mene# (e a!ua. =7. E'ita en l% $%#i5le el t an#$% te (e #u#tancia# +umica# a #u# me#a# (e t a5a2%. =8. U#a e6actamente la# canti(a(e# (e eacti'% +ue #e (an en el $ %ce(imient%. =E. E'ita e! e#a $e+ue,a# canti(a(e# (e eacti'% al & a#c% % i!inal $a a n% c%ntamina l%. 3 F-CV3-3B-2 REV. JUNIO 2007

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20. Fi #e $ %(ucen (e ame# $e+ue,%# (e5en lim$ia #e inme(iatamente. 2=. 7a'a #e la# man%# (e#$u4# (el u#% (e #u#tancia# +umica#. 22. Al encen(e un mec.e % n% (e5e e#ta al & ente (e la #ali(a (e !a#. 23. U#a 5a,% ma ia $a a calenta #u#tancia# in&lama5le#. 2A. E'ita c%l%ca l%# mate iale# en la % illa (e la me#a. 2B. Ga1 un #iti% e6clu#i'% $a a 5a#u a 1 (e#ec.%# #0li(%# >n% (e2a l% #%5 e la me#a (e t a5a2%? 2C. Al a5an(%na el la5% at% i%/ t%(% el mate ial +ue(a " lim$i% 1 ec%!i(%/ ent e!"n(%le al (ele!a(%. 27. 8%(a# la# lla'e# (e !a#/ a!ua (e5en +ue(a ce a(a# ante# (e #ali (el la5% at% i%. 28. Ante# (e #ali (el la5% at% i%/ l"'ate la# man%# FIE;DRE. 2E. Cual+uie (u(a +ue $ue(a tene ace ca (e l%# e6$e iment%# +ue 'a a eali*a la c%n#ulta " c%n el $ %&e#% . 30. E# mu1 im$% tante +ue ca(a alumn% $ e$a e 1 e#tu(ie #u $ "ctica ante# (e lle!a al la5% at% i%.

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!R#CTIC# N* + R"#CCION"$ D" C#R#CT"RI,#CIN D" #LCO-OL"$ +.) + Marco te/rico 7%# alc%.%le# #%n a+uell%# c%m$ue#t%# % !"nic%# +ue $%#een ! u$% &unci%nal %6.i( il% >R0O-? 1 l%# &en%le# >#r0O-?. E#t uctu almente #e $a ecen al a!ua.

Caracter1tica12 - Aun+ue la e#t uctu a (el alc%.%l 1 &en%l #%n #imila e#/ al!una# (e #u# $ %$ie(a(e# +umica# #%n (i&e ente#. - E#t% e#/ $% +ue el ! u$% OG/ tiene un c%m$% tamient% (i#tint% cuan(% e#ta enla*a(% a un ! u$% a il/ en el &en%l/ +ue cuan(% e#ta enla*a(% a un al+uil/ en el alc%.%l. Fenol #lcohol

C-. 3 C-4 3 C-4 3 O7%# alc%.%le# #%n el ! u$% (e c%m$ue#t%# +umic%# +ue e#ultan (e la #u#tituci0n (e un% % 'a i%# "t%m%# (e .i( 0!en% >G? $% ! u$%# .i( %6il% >-OG? en l%# .i( %ca 5u %# #atu a(%# % n% #atu a(%#. En el alc%.%l/ el ! u$% C-OG #e (en%mina ! u$% ca 5in%l. A# el n-me % (e GC enla*a(%# al ca 5in%l (ete mina la cla#e !ene al (el alc%.%l. - Cuan(% .a1 un GC enla*a(% al ca 5in%l/ ent%nce# #e t ata (e un alcohol pri5ario)

- )%# GC uni(%# al ca 5in%l/ #e llama alcohol 1ec6ndario)

- 8 e# GC uni(%# al ca 5in%l/ alcohol terciario. B F-CV3-3B-2 REV. JUNIO 2007

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- 7%# alc%.%le# #%n .i( 06i(%# al+ulic%#H l%# &en%le# .i( 06i(%# a ilc%#.

+.)4 Co5petencia1 - E#tu(ia la# $ %$ie(a(e# +umica# (e l%# alc%.%le# 1 &en%le#. - Reali*a eacci%ne# (e ca acte i*aci0n 1 (i&e enciaci0n (e alc%.%le# 1 &en%le# +.). Materiale1 y e76ipo1 - BeaIe # - 8u5%# (e en#a1% - J;nOA - C 2O7J2 - G2FOA c%ncent a(% - A!ua (e 5 %m% - FeCl3 - Etan%l - 2-5utan%l - F%(i% met"lic% - 8e -5utan%l - Fen%l +.)8 !rocedi5iento +) Di1poner . t69o1 de pr6e9a: a ca(a tu5% a! 4!uele 0/B m7 (e J2C 2O7 1 I !%ta (e G2FOA a? 8u5% = K 0/B m7 etan%l 5? 8u5% 2 K 0/B m7 2-5utan%l c? 8u5% 3 K 0/B m7 te -5utan%l A!ita l%# 3 tu5%# 1 lle'a a 5a,% ma a >B;? $% 2-B minut%#. O5#e 'e 1 an%te #u# e#ulta(%#. 4) Di;erenciaci/n de alcohole1 con 1odio 5et<lico )i#$%ne 3 tu5%# (e $ ue5a a? 8u5% = K = m7 etan%l 5? 8u5% 2 K = m7 2-5utan%l c? 8u5% 3 K = m7 te -5utan%l A ca(a un% a! e!a le un t %cit% (e #%(i% met"lic%. An%ta el tiem$% +ue (u a el (e#$ en(imient% (e .i( 0!en% 1 la 'el%ci(a( c%n +ue e#te #e (e#$ en(a. C F-CV3-3B-2 REV. JUNIO 2007

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.) !r6e9a con el clor6ro ;=rrico) )i#$%ne (e 2 tu5%# (e $ ue5a. a? =m7 etan%l K = !%ta FeCl3 5? =m7 &en%l K = !%ta FeCl3 A!ita / %5#e 'e 1 an%te l%# e#ulta(%#. 8) !r6e9a con el a>6a de 9ro5o) )i#$%ne (e 2 tu5%# (e en#a1%. a? =m7 etan%l K = !%ta a!ua (e 5 %m% 5? =m7 &en%l K = !%ta a!ua (e 5 %m% A!ita / %5#e 'e 1 an%te l%# e#ulta(%#. 7a a$a ici0n (e un $ eci$ita(% 5lanc% e# >K?. +.)? Re16ltado1 Fe eali*0 eacci%ne# (e ca acte i*aci0n 1 (i&e enciaci0n #e l%# alc%.%le# 1 &en%le#. +.)@ C6e1tionario +) Ga!a la ecuaci0n e(%6 $a a la e(ucci0n (el C KC en la eacci0n (e %6i(aci0n (e l%# alc%.%le#. 4) Ga!a la ecuaci0n $a a la $ ue5a (el FeCl3 c%n etan%l 1 c%n &en%l .) )e#(e el $unt% (e 'i#ta In(u#t ial c%m% #e %5tienen l%# alc%.%le# 8)0 Realice la ecuaci0n +umica (el alc%.%l c%n el #%(i% met"lic%. +.)A F6ente1 de in;or5aci/n =. V%!elL# Elementa 1 D actical O !anic C.emi#t 1 =. 7%n!man 3 %u$/ =E80. 2. ;u,%* ;ena. 7a E6$e imentaci0n en Qumica O !"nica. D ime a e(ici0n. Du5licaci%ne# Cultu al F.A. ;46ic% =E7B. 3. )%mn!ue* M. E6$e iment%# (e Qumica O !"nica. E(it% ial 7imu#a-Nile1 F.A. =E73. A. B eO#te . R. Van(ee Oe t ;c EOen N. Cu #% D "ctic% (e Qumica O !"nica. E). Al.am5 a F. A. ;a( i(. =E82.

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!R#CTIC# N* 4 O'T"NCIN D" #LCO-OL"$ +8) + Marco te/rico En una me*cla (e alc%.%l 1 a!ua $ue(e (ete mina #e el ! a(% alc%.0lic% mi(ien(% la (en#i(a( (e mane a (i ecta c%n un alc%.%lmet % % lue!% (e un $ %ce#% llama(% (e (e#tilaci0n. 7a de1tilaci/n e# una %$e aci0n me(iante la cual #e$a am%# (%# % m"# l+ui(%# mi#ci5le# (e una me*cla me(iante $ %ce#%# alte na(%# (e e'a$% aci0n 1 c%n(en#aci0n. E6i#ten (i#tint%# ti$%# (e (e#tilaci0n< )e#tilaci0n #im$le. )e#tilaci0n & acci%na(a. +8)4 Co5petencia1 - E#tu(ia la# $ %$ie(a(e# +umica# (e l%# alc%.%le# 1 &en%le#. - Reali*a eacci%ne# (e ca acte i*aci0n 1 (i&e enciaci0n (e alc%.%le# 1 &en%le# +8). Materiale1 y e76ipo1 ;at a* (e 2B0 ml Ca5e*a (e (e#tilaci0n Re& i!e ante (e 5%la# D %5eta (e =00m7 ;an!ue a# (e e& i!e ante Em5u(% c0nic% 8e m0met % 7una (e el%2 Di$eta Va#% (e $ eci$ita(% 8u5%# (e en#a1% Din*a $a a tu5% (e en#a1% Re& i!e ante ect% 8 $%(e Re2illa (e a#5e#t% C"$#ula (e $% celana ;ec.e % Din*a $ic% (e l% % E#$"tula Va#% (e $ eci$ita(% 3 a(illa $a a tu5%# (e en#a1% +8)8 !rocedi5iento

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Int %(u*ca 80 m7 (e la mue#t a $ %5lema (e #%luci0n alc%.0lica en un mat a* (e (e#tilaci0n >2B0m7? a me un #i#tema (e (e#tilaci0n/ #e!-n #e mue#t a en l% in(ica(% $% el $ %&e#% . )e#tile c%n cui(a(% 'e i&ican(% +ue el cal% a$lica(% n% #ea mu1 &ue te/ (e mane a +ue l%# 'a$% e# a#cien(an lentamente 1 #e (e#tile (e una a (%# !%ta# $% #e!un(% >a$ %6ima(amente?/ t%man(% l%# 'al% e# (e la tem$e atu a ca(a minut%. An%te la tem$e atu a (e (e#tilaci0n 1 c%m$a e c%n la tem$e atu a (e e5ullici0n te0 ica. +8)? Re16ltado1 Fe eali*0 la %5tenci0n (e alc%.%l. +8)@ C6e1tionario =. ;enci%ne %t %# m4t%(%# $a a %5tene l%# alc%.%le#. 2. Inte $ ete l%# e#ulta(%# %5teni(%#. +8)A F6ente1 de in;or5aci/n =. V%!elL# Elementa 1 D actical O !anic C.emi#t 1 =. 7%n!man 3 %u$/ =E80. 2. ;u,%* ;ena. 7a E6$e imentaci0n en Qumica O !"nica. D ime a e(ici0n. Du5licaci%ne# Cultu al F.A. ;46ic% =E7B. 3. )%mn!ue* M. E6$e iment%# (e Qumica O !"nica. E(it% ial 7imu#a-Nile1 F.A. =E73. A. B eO#te . R. Van(ee Oe t ;c EOen N. Cu #% D "ctic% (e Qumica O !"nica. E). Al.am5 a F. A. ;a( i(. =E82.

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!R#CTIC# NB . #MIN#$)0 D"T"RMIN#CIN D" L#$ C#R#CT"RC$TIC#$ FC$IC#$ % DUCMIC#$ D" COM!U"$TO$ #MIN#DO$ I) INTRODUCCIN #5ina, n%m5 e +ue eci5en l%# c%m$ue#t%# $ %(uci(%# a menu(% en la (e#c%m$%#ici0n (e la mate ia % !"nica/ +ue #e &% man $% #u#tituci0n (e un% % 'a i%# "t%m%# (e .i( 0!en% (el am%nac% $% ! u$%# % !"nic%#. El n-me % (e ! u$%# % !"nic%# uni(%# al "t%m% (e nit 0!en% (ete mina +ue la m%l4cula #ea cla#i&ica(a c%m% amina $ ima ia >un ! u$% % !"nic%?/ #ecun(a ia >(%# ! u$%#? % te cia ia >t e# ! u$%#?. 7a ma1% a (e la# amina# tienen un %l% (e#a! a(a5le 1 #%n #%lu5le# en a!ua. Fu# $unt%# (e e5ullici0n #%n #u$e i% e# a l%# .i( %ca 5u %# (e an"l%!a ma#a m%lecula e in&e i% e# a l%# c% e#$%n(iente# alc%.%le#. Ve em%# al!una# ca acte i*a# (e la# amina# C%m$ue#t%# inc%l% %# Fe %6i(an c%n &acili(a( l% +ue le# $e miten c%n'e ti #e en C%m$ue#t%# c%l% a(%# 7%# $ ime %# miem5 %# (e e#ta #e ie #%n !a#e# +ue tienen %l% a am%niac% A me(i(a +ue aumenta el n-me % (e "t%m%# (e ca 50n en la m%l4cula/ el %l% #e .ace #imila al $e#ca(%. 7a# amina# tienen ca "cte 5"#ic%H #%n 5a#e# m"# &ue te# +ue el a!ua 1/ en !ene al/ +ue el am%nac%. El $ inci$al m4t%(% (e %5tenci0n (e e#t%# c%m$ue#t%# e# la eacci0n ent e el am%nac% 1 un .al%!enu % (e al+uil%. Una (e la# amina# m"# im$% tante# e# la anilina/ la amina a %m"tica m"# #encilla. F%lu5ili(a(< 7a# amina# $ ima ia 1 #ecun(a ia# #%n $%la e# ca$ace# (e &% ma $uente# (e .i( 0!en% ent e #i 1 c%n el a!ua e#t% #e .ace #%lu5le en ella#. 7a #%lu5ili(a( (i#minu1e en la# m%l4cula# c%n #ei# "t%m%# (e ca 5%n% 1 en la# +ue $%#ee el anill% a %m"tic%. II) COM!"T"NCI#$ - E#tu(ia la# $ %$ie(a(e# +umica# (e 7a# Amina#. - Reali*a eacci%ne# (e ca acte i*aci0n 1 (i&e enciaci0n (e Amina#/ III. M#T"RI#L"$ % R"#CTI O$ - BeacIe 2B0 m7 - Em5u(% (e #e$a aci0n - #ul&at% (e c%5 e - Pci(% #ul&- ic% - 8u5%# (e en#a1% -Cl% %&% m% - Nit %5encen% - Gie % en $%l'% - NaOG - acet%na - nit %$ u#iat% (e #%(i% -Da$el $G -Cl% u % &4 ic% -Fen%l&talena -C %mat%&%li% - GCl c%ncent a(% -Bencen% -am%niac% -8%lui(ina -acetanili(a -(imetilanilina -anilina

I ) !ROC"DIMI"NTO "E!"RIM"NT#L =0 F-CV3-3B-2 REV. JUNIO 2007

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!RO!I"D#D"$ D" L#$ #MIN#$ =.- Ca "cte 5"#ic% (e la# amina#< )i#$%ne (e 0C tu5%# (e en#a1% en ca(a un% (e ell%# a! e!a una# !%ta# (e la mue#t a $ %5lema #e a!itan c%n B m7 (e a!ua 1 #e en#a1a #u eacci0n c%n $a$el $G/ lue!% (e (ete mina el $G/ a! e!a una# !%ta# (e la #%luci0n in(ica(% a (e &en%l&talena/ %5#e 'e 1 an%te #u# e#ulta(%#. 2.- )i#$%ne (e 0C tu5%# (e en#a1% en ca(a un% (e ell%# a! e!a una# !%ta# (e la mue#t a $ %5lema #e a!itan c%n B m7 (e a!ua 1 #e a,a(e 2 m7 (e una #%luci0n (e cl% u % &4 ic% 3.- )i#$%ne (e 0C tu5%# (e en#a1% en ca(a un% (e ell%# a! e!a una# !%ta# (e la mue#t a $ %5lema #e a!itan c%n B m7 (e a!ua c%l%ca en ca(a tu5% (e en#a1% !%ta# (e una #%luci0n (e #ul&at% (e c%5 e/ #i #e %5#e 'a a una c%l% aci0n 'e (%#a/ in(ica a +ue la eacci0n e# $%#iti'a. A.- Reacci0n (e Rimini< )i#$%ne (e 0C tu5%# (e en#a1% en ca(a un% (e ell%# a! e!a una !%ta# (e la mue#t a $ %5lema 1 a! e!a = m7 (e acet%na 1 una !%ta (e nit %$ u#iat% (e #%(i% eci4n $ e$a a(%/ a$a ece " (ent % (e un minut% una c%l% aci0n %2% 'i%leta. B.- F% maci0n (el #ul&at% "ci(%< En un 'i( i% (e el%2 c%l%ca una !%ta (e "ci(% #ul&- ic% 1 una !%ta (e la mue#t a $ %5lema/ %5#e 'e 1a n%te #u# e#ulta(%#. C.- F% maci0n (el cl% .i( at%< En un 'i( i% (e el%2 c%l%ca una !%ta (e la mue#t a $ %5lema 1 una !%ta (e "ci(% cl% .( ic% c%ncent a(%/ %5#e 'e 1a n%te #u# e#ulta(%#. ) CU"$TION#RIO =.- Realice la# ecuaci%ne# +umica# +ue #e .a $ %(uci(% al eali*a el e6$e iment% 2.- )i!a U(. A $a ti (e +ue amin%"ci(%# #e &% man la ca(a'e ina 1 $ut e#cina. 3.- In'e#ti!ue +ue %t a# eacci%ne# +umica# #e $ue(en eali*a $a a ca acte i*a a la# Amina#.

== F-CV3-3B-2

REV. JUNIO 2007

QUMICA ORGANICA 2014

!R#CTIC# NB 8 #MIN#$)0 $CNT"$I$ D" L# #NILIN# # !#RTIR D" L# #C"T#NILID# INTRODUCCIN E#t uctu a ;%lecula < El "t%m%# (e nit 0!en% en am%na# $%#ee una .i5 i(i#m% #$3 1 (%# elect %ne# (e#a$e a(%# $% l% +ue e#t%# c%m$ue#t%# $ e#entan una e#t uctu a tet a!%nal/ el cent % l% c%n#titu1e el nit 0!en% 1 $%#ee '4 tice# (e =0EQ. 7a# amina# a %m"tica# #%n mu1 t%6ica# 1 #e a5#% 5en $% me(i% (e la $iel. 7a# amina# #e %5tienen $% e(ucci0n (e nit il%# 1 ami(a# c%n el .i( u % (e liti% 1 alumini%. 7a t an#$%#ici0n (e G%&mann c%n'ie te la# ami(a# en amina# c%n un ca 5%n% men%#. 7a e(ucci0n (e a*i(a# $e mite %5tene amina# c%n el mi#m% n-me % (e ca 5%n%# +ue el .al%alcan% (e $a ti(a. 7a #nte#i# (e 3a5 iel $e mite %5tene amina# a $a ti (el "ci(% &t"lic%. COM!"T"NCI#$ - C%m$ en(e e inte $ eta la %5tenci0n (e amina# - Reali*a eacci%ne# (e ca acte i*aci0n en i(enti&icaci0n (e Amina#. M#T"RI#L"$ % R"#CTI O$ - BeacIe 2B0 m7 -Da$el $G - Em5u(% (e #e$a aci0n -#ul&at% (e c%5 e =0R - Pci(% #ul&- ic% -C %mat%&%li% - 8u5%# (e en#a1% -Cl% %&% m% - GCl c%ncent a(% -Bencen% - acetanili(a -Fen%l&talena - anilina -NaOG =0R - cl% u % &4 ic% =0R !ROC"DIMI"NTO "E!"RIM"NT#L En un tu5% (e en#a1% c%l%ca 0/700 ! (e acetanili(a/ 2/B m7 (e a!ua (e#tila(a/ 3 m7 (e GCl c%ncent a(% >a,a(i =/B m7 1 lue!% l%# %t %# =/B m7?/ #e a!ita 1 #e c%l%ca en 5a,% ;a a $% 20 minut%# a$ %6ima(amente. )ete mina el $G 1 a! e!a NaOG .a#ta neut ali*a la #%luci0n. I(enti&icaci0n (e la anilina $% c %mat%! a&a en ca$a &ina < #i#tema (e #%l'ente< cl% %&% m% % 5encen%. Re'ela(% < 'a$% e# (e I%(% met"lic%. !RO!I"D#D"$ D" L#$ #MIN#$ F#NILIN#G =.- Ca "cte 5"#ic% (e la anilina< una# !%ta# (e anilina #e a!itan c%n B m7 (e a!ua 1 #e en#a1a #u eacci0n c%n $a$el $G % c%n #%luci0n in(ica(% a (e &en%l&talena. 2.- Una# !%ta# (e anilina #e a!itan c%n B m7 (e a!ua 1 #e a,a(e 2 m7 (e una #%luci0n (e cl% u % &4 ic%. 3.- C%l%ca en un tu5% (e en#a1% #%luci0n (e #ul&at% (e c%5 e 1 a! e!a anilina/ #e %5#e 'a a una c%l% aci0n 'e (%#a. ) CU"$TION#RIO =.- Realice la# ecuaci%ne# +umica# +ue #e .a $ %(uci(% al eali*a el e6$e iment% 2.- )i!a U(. 7a# $ %$ie(a(e# +umica# (e la# amina 1 +ue &act% e# a&ectan la 5a#ici(a(.. 3.- )e e2em$l%# (e #u#tancia# c%n acti'i(a( &a mac%l0!ica +ue ten!an en #u e#t uctu a +umica amina.

=2 F-CV3-3B-2

REV. JUNIO 2007

QUMICA ORGANICA 2014

!R#CTIC# NB ? R"#CCION"$ D" C#R#CT"RI,#CIN D" #LD"-CDO$ % C"TON#$) INTRODUCCION 7a c%m$a tici0n (e cuat % elect %ne# ent e (%# "t%m%# (e ca 5%n% c%n#titu1e el (%5le enlace CS C. El ca 5%n% $ue(e &% ma (%5le# enlace# c%n %t %# "t%m%#/ c%m% l%# m%#t a(%# en l%# #i!uiente# e2em$l%#< CH O Car9onilo CHN I5ino CH$ Tiocar9onilo

El enlace m"# & ecuente e# el (%5le enlace Ca 5%n%- O6i!en% +ue c%n#titu1e la uni(a( e#t uctu al c%n%ci(a c%m% ! u$% ca 5%nlic%. E7 ! u$% ca 5%nil% e# el ! u$% &unci%nal ca acte #tic% (e l%# al(e.(%# 1 cet%na#/ "ci(%# ca 5%6lic%# 1 #u# (e i'a(%#. E# el ! u$% &unci%nal m"# im$% tante en la +umica O !"nica. En l%# al(e.(%# el ! u$% Ca 5%nill% lle'a un "t%m% (e Gi( %!en% 1 un% (e %6!en%. 7a e#t uctu a !ene al (e l%# al(e.(%# e#< R T CGO en la +ue R $ue(e #e Al+uil% % A il%. Cuan(% l%# (%# ! u$%# uni(%# al ! u$% Ca 5%nill% #%n ! u$%# Al+ulic%# % A lic%#. 7a e#t uctu a !ene al (e la# Cet%na# e#< R-CO TR 7a natu ale*a (e R $ue(e 'a ia mu1 am$liamente/ en la +ue R/ RU $ue(en #e Al+ulic%/ A lic% % mi6t%. El ! u$% Ca 5%nil%/ e#t" &% ma(% $% un "t%m% (e Ca 5%n% 1 un "t%m% (e O6!en% uni(%# $% un (%5le enlace 1 $% l% tant% tienen una #eme2an*a &% mal c%n el (%5le enlace tant% tienen una #eme2an*a &% mal c%n el (%5le enlace %le&nic%/ $e % e6i#te una n%ta5le (i&e encia ent e el enlace CSO 1 el enlace CSC (e5i(% a la ma1% elect %ne!ati'i(a( (el %6!en% c%m$a a(% c%n el Ca 5%n%/ en c%n#ecuencia el ! u$% Ca 5%nill% eacci%na m"# &"cilmente/ 1 c%n ma1% 'a ie(a( (e eacti'% (e +ue un (%5le enlace Ca 5%n%-Ca 5%n%. 7a eacti'i(a( (e l%# Al(e.(%# 1 Cet%na# (e5i(% al ca "cte n% #atu a(% (el ! u$% Ca 5%nil%/ (a lu!a a eacci%ne# +umica# c%mune# en am5%# ti$%# (e #u#tancia/ tale# c%m%< a(ici0n 5i#ul&tica/ c%n(en#aci0n/ $%lime i*aci0n 1 %6i(aci0n. )ent % (e la# eacci%ne# +ue e'i#ten ! an im$% tancia/ e#t"n la# eacci%ne# +ue n%# $e miten &% ma (e i'a(%# #0li(%# a $a ti (e Al(e.(%# 1 cet%na# l+ui(%#/ l%# cuale# n%# $e miten $u i&ica la#/ e i(enti&ica la#/ (ent % (e ella# e#t"n la &% maci0n (e< OMI;AF/ al eacci%na c%n Gi( %6ilamina >NG2 OG? GI)RAVO;AF/ al eacci%na c%n Gi( acina >NG2- NG2? FENI7IGI)RAVONA/ al eacci%na c%n Fenil.i( acina >D.- NG-NG2? 2/A-)INI8ROFENI7IGI)RAVONA/ al eacci%na c%n 2/A-(init %&enil.i( acina. E#t%# n% $e miten %5tene (e i'a(%# #0li(%# c i#talin%# (e $unt% (e &u#i0n (e&ini(%/ #ien(% $% ell% a(ecua(a# $a a la %5tenci0n e i(enti&icaci0n (e c%m$ue#t%# Ca 5%nlic%#< Al(e.(%# 1 Cet%na#. 7a (i&e enciaci0n +umica ent e Al(e.(%# 1 Cet%na#/ #e 5a#a en &acili(a( c%n +ue l%# al(e.(%# #e %6i(an a "ci(%# Ca 5%6lic%# & ente a cie t%# eacti'%# 1 en la e#ta5ili(a( (e la cet%na & ente a l%# mi#m%# c%m% $% e2em$l% c%n el eacti'% (e 8%llen#/ c%n el eacti'% (e Fe.lin!/ en l%# +ue #e $ %(ucen e(ucci%ne# (e l%# Al(e.(%# (an(% lu!a a la &% maci0n (e $lata met"lica 1 %6i(% Cu$ c% e#$ecti'amente. Una eacci0n +ue n%# $e miten #e$a a un Al(e.(% % una Cet%na (e una me*cla (e c%m$ue#t%# % !"nic%# e# .acien(% la eacci%na c%n Bi#ul&it% (e #%(i%/ $% e#te me(i% #e %5tiene c%m$ue#t%# (e a(ici0n 5i#ul&itica +ue #%n #0li(%# c i#talin%#. E#ta eacci0n e# $%#iti'a $a a t%(%# l%# Al(e.(%# 1 $a a la# ;etilcet%na#. 7a a(ici0n 5i#ul&itica e# una =3 F-CV3-3B-2 REV. JUNIO 2007

QUMICA ORGANICA 2014

eacci0n e'e #i5le/ $% l% +ue #e $ue(e e!ene a el c%m$ue#t% Ca 5%nlic% inicial/ $a a ell% el $ %(uct% #e (i#uel'e en a!ua 1 #e le a(ici%na Na2CO3 % un "ci(% (ilui(% $a a (e#t ui el 5i#ul&it% (e #%(i%. 7%# Al(e.(%# 1 Cet%na# tienen %l% 1 #a5% ca acte #tic% 1 a ell% #e (e5e 2unt% c%n l%# "ci(%# ! a#%# '%l"tile#/ el #a5% (e aliment%# a,e2%# 1 anci%#. COM!"T"NCI# -C%m$ %5a W (e(uci el c%m$% tamient% (e l%# al(e.(%# 1 la cet%na# & ente a la &enil.i( acina % #u (e i'a(% 2-A- (init %&enil( acina. -A$lica $ ue5a# #encilla# +ue $e mitan (i#tin!ui #i un c%m$ue#t% ca 5%nlic%/ $e tenece al ! u$% (e l%# al(e.(%# % al ! u$% (e la# cet%na#. M#T"RI#L"$ % R"#CTI O$ - 8u5%# (e en#a1% - Re2illa (e a#5e#t% - 8 i$%(e - Di$eta - BeacIe -;ec.e % - F%luci0n alc%.0lica (e 5en*al(e.(% - Gi( 06i(% (e am%ni% c%nc. - Reacti'% 2/A-(init %&enil.i( acina - Acetal(e.(% - Cicl%.e6an%na - Nit at% (e $lata =0R - Reacti'% (e Fc.i&& - F%luci%ne# (e NaOG al =0R - Reacti'% (e Fe.lin! 9A: 1 9B: - F%l. Fatu a(a (e 5i#ul&it% (e #%(i% - D %$an%na >acet%na? - ;etan%l - Pci(% cl% .( ic% - Ca 5%nat% (e #%(i% !#RT" "E!"RIM"NT#L +)0 R"#CCION CON L# 4,8 DINITROF"NIL-IDR#CIN# C%l%ca un tu5% (e en#a1% una #%luci0n alc%.0lica (e 5en*al(e.(% >0/B m7? 1 a(ici%na le el eacti'% 2/A- (init %&enil.i( acina >!%ta#? %5#e 'a 1 an%ta l%# e#ulta(%#. 4)0 R"#CCION D" $C-IFF )i#$%ne (e 2 tu5%# (e en#a1% Al tu5% NX= a(ici%na le Acetal(e.(% >V !%ta#? 1 a! e!a le el eacti'% (e Fc.i&& >0/Bm7? Al tu5% NX2 a(ici%na le cicl%.e6an%na >V !%ta#? 1 a! e!a le el eacti'% (e Fc.i&& >0/Bm7? O5#e 'a 1 an%ta l%# e#ulta(%# .)0 R"#CCION D" TOLL"N$ En un tu5% (e en#a1% a! e!a = m7 (e una #%luci0n (e nit at% (e $lata 1 una !%ta (e .i( 06i(% (e #%(i% =0 R/ el $ eci$ita(% &% ma(% (i#%l'e l% a,a(ien(% .i( 06i(% (e am%ni%/ lue!% (i'i(i la #%luci0n en (%# tu5%# (e en#a1% en $a te# i!uale#< Al tu5% X= a(ici%na le =m7 (e #%luci0n (e Acetal(e.(% Al tu5% X2 a(ici%na le =m7 (e #%luci0n (e Cicl%.e6an%na 7le'a l%# tu5%# a 5a,% ma a $% e#$aci% (e = minut%. O5#e 'e #i .a1 &% maci0n (e un $ eci$ita(% ne! % % un e#$e2% (e $lata .An%te l%# e#ulta(%#. 8)0 R"#CCION D" F"-LINI En un tu5% (e en#a1% $ e$a a la #%luci0n (e Fe.lin! a! e!an(% $a te i!uale# (e Fe.lin! A 1 Fe.lin! B >=m7 (e ca(a un%?. 7ue!% (i'i(i l% en (%# tu5%#< Al tu5% NX = a! e!a le acetal(e.(% >V !%ta#? Al tu5% NX 2 a! e!a le cicl%.e6an%na >V !%ta#? Am5%# tu5%# lle'a a 5a,% ma a a e5ullici0n $% 3 minut%# %5#e 'e 1 an%te l%# e#ulta(%#. 7a eacci0n e# $%#iti'a cuan(% a$a ece un $ eci$ita(% %2% $a (%. ?)0 #DICIN D"L 'I$ULFITO D" $ODIO =A F-CV3-3B-2 REV. JUNIO 2007

QUMICA ORGANICA 2014

En un tu5% (e en#a1% a! e!a = m7 (e una #%luci0n #atu a(a (e 5i#ul&it% (e #%(i% 1 0/7 m7 (e metan%l 1 lue!% a,a(a lentamente 0/B m7 (e $ %$an%na/ a!ite en4 !icamente 1 en& e la #%luci0n c%n .iel%/ Filt e 1 (i'i(a el $ eci$ita(% en (%# tu5%# (e en#a1%/ a un% #e le a! e!a ca 5%nat% (e #%(i% 1 a!ua/ an%te l% +ue #uce(a. A la #e!un(a $% ci0n #e le a,a(en B m7 (e "ci(% cl% .( ic%/ an%te l%# cam5i%# +ue %cu an. CU"$TION#RIO =.- Realice la# ecuaci%ne# +umica# (e ca(a una (e la# eacci%ne# eali*a(a#. 2.- ;enci%ne al!un%# al(e.(%# 1 cet%na# +ue &% men $%lme %# 1 ten!an im$% tancia &a mac4utica. 3.- Cu"l e# la im$% tancia (e la eacci0n c%n la 2/A-(init %&enil.i( acina 1 ealice #u ecuaci0n +umica c%m$leta. D %$%n!a un mecani#m% (e

=B F-CV3-3B-2

REV. JUNIO 2007

QUMICA ORGANICA 2014

!R#CTIC# NB @ R"#CCION"$ D" #LD"-CDO$ % C"TON#$) O'T"NCIN D" L# C#NFOROEIM# INTRODUCCIN 7%# c%m$ue#t%# ca 5%nlic%# al(e.(ic%# 1 cet0nic%# #e ca acte i*an $% +ue #u# e#t uctu a# $%#een un ! u$% (en%mina(% ca 5%nil%. E#te e#t" uni(% a (%# ca 5%n%# en el ca#% (e la# cet%na#/ $a a el ca#% (e l%# al(e.(%# #e unen a un "t%m% (e ca 5%n% y a un "t%m% (e .i( 0!en%. R - CO T R Cet%na R - CGO Al(e.(%

7a eacti'i(a( (e l%# al(e.(%# 1 la# cet%na# #e (e5e a la $%la i*aci0n (el ! u$% ca 5%nil% +ue in'%luc a el e&ect% in(ucti'% 1 el e&ect% e#%nante. 7a# eacci%ne# m"# im$% tante# #%n la# (e a(ici0n/ (e a(ici0n-(e#.i( ataci0n 1 la# eacci%ne# 'a i0n ca 5ani0n. El ! u$% ca 5%nil% $%#ee $ %$ie(a(e# +umica# +ue l% .acen el cent % (e eacci0n. Una (e la# eacci%ne# m"# ca acte #tica# #%n la# eacci%ne# (e a(ici0n. Ent e ella# ca5e (e#taca la eacci0n (e a(ici0n (e la# &enil.i( a*%na/ +ue #e $ %(uce al .ace eacci%na un al(e.(% % cet%na c%n una &enil.i( acina. E#ta# eacci%ne# c%m$ en(en t e# $a#%#< 7a $ %t%ni*aci0n (el ! u$% ca 5%nil%/ la &% maci0n (el $ %(uct% (e a(ici0n 1 la (e#.i( ataci0n. COM!"T"NCI#$ =. E6$lica 1 (e#c i5e la# eacci%ne# a ni'el (el ! u$% ca 5%nil%. 2. Ca acte i*a e i(enti&ica el c%m$ue#t% #inteti*a(%. M#T"RI#L"$ % R"#CTI O$ ;A8ERIA7E F Bal0n (e (e#tilaci0n Re& i!e ante ;ec.e % 8 $%(e Re2illa (e a#5e#t% 8u5%# (e en#a1% 3 a(illa Di$eta# BeaIe Em5u(%# REAC8IVOF Alcan&% Alc%.%l etlic% EBQ Gi( %6ilamina Acetat% (e #%(i% GCl Acetat% (e etil% n-.e6an% Filica!el 3C0 Y%(% met"lic%

!#RT" "E!"RIM"NT#L O'T"NCIN D" L# C#NFOROEIM#2 En un 5al0n (e =00 m7 c%l%ca 0/= ! (e alcan&% / a(ici%na alc%.%l etlic% EBR =/B m7/ a!ita $a a (i#%l'e l%# c i#tale#. A! e!a 0/2 m. (e #%luci0n (e .i( %6ilamina/ a!ita 1 lle'a a e&lu2% $% a$ %6ima(amente B0 minut%#. En& ia a c.% % (e a!ua/ lue!% =C F-CV3-3B-2 REV. JUNIO 2007

QUMICA ORGANICA 2014

a(ici%na 3/0 m7 (e a!ua (e#tila(a 1 %5#e 'a la &% maci0n (e un $ eci$ita(%. A! e!a 0/A a 0/ B m7 (e GCl BR 1 &ilt a al 'ac%/ #eca en la e#tu&a l%# c i#tale# %5teni(%#. Fe c%m$ %50 la %5tenci0n (el $ %(uct% me(iante c %mat%! a&a en ca$a &ina. F%$% te< Filica!el 3 acti'a(% Fi#tema (e #%l'ente#< Acetat% (e Etil% - n-.e6an% >2<0/B? Re'ela(% < Va$% e# (e I%(% CU"$TION#RIO =. Inte $ ete l%# e#ulta(%# %5teni(%#. 2. Realice la ecuaci0n 1 #u mecani#m% (e acci0n c% e#$%n(iente. 3. ;enci%ne al!un%# c%m$ue#t%# +ue $ e#enten im$% tancia en la In(u#t ia &a mac4utica.

=7 F-CV3-3B-2

REV. JUNIO 2007

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!RJCTIC# N* A R"#CCION"$ I# C#R'#NIN2 COND"N$#CIN D"L #CIDO '#R'ITKRICO % '"N,#LD"-CDO INTRODUCCIN 7%# c%m$ue#t%# ca 5%nlic%# +ue #%n al(e.(%# a %m"tic%# #e c%n(en#an $% acci0n (e 5a#e#/ c%n cet%na#/ c%n metilen% acti'%/ (an(% un $ %(uct% (e a(ici0n #e!ui(% (e (e#.i( ataci0n/ e#ta eacci0n en e#$ecial #e (en%mina Reacci0n (e Jn%e'ena!el. E#ta c%n(en#aci0n #e lle'a a ca5% $% la &% maci0n (e un ca 5ani0n/ &acilita(a $% la inte acci0n c%n una 5a#eH 1 la a(ici0n nucle%&lica c%n el %t % c%m$ue#t% ca 5%nlic%. D% -ltim% e#te c%m$ue#t% #e (e#.i( ata &% man(% un (%5le enlace en l%# ca 5%n%# Z 1 l% +ue #e (en%mina c%n(en#aci0n al(0lica. COM!"T"NCI#$ =. E6$lica 1 c%n%ce la# eacci%ne# al ! u$% ca 5%nil% 'a ca 5ani0n. 2. I(enti&ica el c%m$ue#t% #inteti*a(% M#T"RI#L"$ % "DUI!O$ ;A8ERIA7E F 3 a(illa -8u5%# (e en#a1% -E#$"tula -Di$eta# ! a(ua(a# -Em5u(% -Da$el (e &ilt % -BeaIe -7amina# $% ta%52et% -;ec.e %# -8 $%(e -Re2illa (e a#5e#t% REAC8IVOF -Pci(% 5a 5it- ic% -Am%niac% -Ben*al(e.(% -;etan%l -Y%(% met"lic% -Filica!el 3C0 -Giel%

DAR8E EMDERI;EN8A7 OB8ENCI[N )E 7A CON)ENFACI[N )E7 PCI)O BARBI8\RICO Y BENVA7)EG])O En un tu5% (e en#a1% lim$i% 1 #ec% #e c%l%ca 0/07 ! (e Pci(% 5a 5it- ic% a,a(i 2 m7 (e am%niac% a!ita 'i!% %#amente $% =0 minut%#/ lue!% #e a! e!a 0/2 m7 (e 5en*al(e.(%/ ta$a 1 a!ita 'i!% %#amente $% =0 minut%# 1 lle'a a e& i!e aci0n. Fe $ %ce(e a &ilt a 1 !ua (a $a a #u i(enti&icaci0n me(iante c %mat%! a&a en ca$a &ina. Fa#e m0'il< ;etan%l F%$% te< Filica!el 3 acti'a(% Re'ela(% < Va$% e# (e Y%(% CUEF8IONARIO =. Inte $ ete l%# e#ulta(%# %5teni(%#. 2. Realice la ecuaci0n 1 #u mecani#m% (e eacci0n c% e#$%n(iente 3. )i!a cuale# #%n l%# (e i'a(%# (e (el "ci(% 5a 5it- ic% 1 cu"l e# #u acti'i(a( &a mac%l0!ica. =8 F-CV3-3B-2 REV. JUNIO 2007

QUMICA ORGANICA 2014

!RJCTIC# N* L #CIDO$ C#R'OEILICO$2 O'T"NCION D"L #CIDO CITRICO . I) INTRODUCCIN 7%# aci(%# ca 5%6ilic%# #%n c%m$ue#t%# % !anic%# +ue #e ca acte i*an $% $%#ee un ! u$% ca 5%6il%. R0 COO7%# (e i'a(%# (e l%# "ci(%# ca 5%6lic%# $ e#entan el ! u$% (en%mina(% acil%/ +ue $ue(e e#ta &% ma(% $% un a(ical ali&"tic% % a %m"tic% uni(% al ! u$% ca 5%nil%. D% e#ta a*0n a l%# "ci(%# ca 5%6lic%# 1 a #u# (e i'a(%# #e le (en%mina/ alte nati'amente/ c%m$ue#t%# aclic%#. EF8ER ANIGI)RI)O )E ACI7O A;I)A GA7URO )E ACI7O

II. CO;DE8ENCIAF Reali*a la %5tenci0n (e un "ci(% ca 5%6lic% Ca acte i*a e i(enti&ica al c%m$ue#t% %5teni(% III. ;A8ERIA7EF Y REAC8IVOF ;A8ERIA7EF 8u5%# (e en#a1% 3 a(illa# BeaIe 6 2B0m7 Em5u(%# Da$el (e &ilt % Di$eta# mec.e % 8 $%(e Re2illa Ba!ueta# E#$"tula# REAC8IVOF Gi( 06i(% (e calci% A!ua (e#tila(a 7im%ne# Da$el In(ica(% Uni'e #al (e $G Pci(%# #ul&- ic% (ilui(% =0R C %mat%&%li%# Ca$ila e# Etan%l Cu5a c %mat%! a&ica I%(% met"lic% O'T"NCIN D"L JCIDO CCTRICO IV. DROCE)I;IEN8O O5tene el 2u!% (e t e# lim%ne#/ (ilui t e# 'ece# #u '%lumen c%n a!ua (e#tila(a 1 lue!% neut ali*a c%n .i( 06i(% (e calci%/ calenta #ua'emente en 5a,% ma a/ lue!% &ilt a la #%luci0n caliente >cit at% (e calci% in#%lu5le en a!ua caliente?. )e2a en e$%#% la #%luci0n $a a +ue el "ci(% ct ic% e#tante c i#talice. )i#%l'e el $ eci$ita(% 1 a,a(i una #%luci0n (e "ci(% #ul&- ic% =0R >!%ta a !%ta? .a#ta la &% maci0n (e un $ eci$ita(%/ &ilt a . 7%# $ eci$ita(%# 2unta l%# 1 $u i&ica l%# me(iante la ec i#tali*aci0n/ el $ %(uct% i(enti&ica l% me(iante C %mat%! a&a. F.E< Filica!el 3 T c %mat%&%li%#. =E F-CV3-3B-2 REV. JUNIO 2007

QUMICA ORGANICA 2014

Fi#tema (e F%l'ente< Re'ela(% < Etan%l Va$% e# (e I%(% met"lic%

CH2 - COOH HO - C - COOH CH2 - COOH cido Ctrico

V. CUEF8IONARIO =. Gace la# ecuaci%ne# (e ca(a un% (e l%# $a#%# en la %5tenci0n (el "ci(% ct ic%. 2. (e#c i5a la %5tenci0n (e un "ci(% ca 5%6lic% %5teni(% (e un $ %(uct% natu al 1 c%m% #e i(enti&ica (ic.% aci(%.

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!RJCTIC# NB M COM!U"$TO$ C#R'OECLICO$2 R"#CCION"$ D" "$T"RIFIC#CIN 3 M&TODO D" TR#N$"$T"RIFIC#CIN INTRODUCCIN 7a e+uili5 aci0n (e un alc%.%l c%n un 4#te +ue c%nten!a un ! u$% alc%6il% (i&e ente e# un m4t%(% $a a la c%n'e #i0n (e un 4#te en %t %. 7%# 4#te e# eacci%nan c%n %t %# alc%.%le# en c%n(ici%ne# "ci(a# % 5"#ica# $a a $ %(uci nue'%# 4#te e#/ 1 e#ta eacci0n #e c%n%ce c%m% t an#e#te i&icaci0n 1a +ue un 4#te #e t an#&% ma en %t %. E#ta# eacci%ne# (e t an#e#te i&icaci0n #%n an"l%!a# a la .i( 0li#i# "ci(a 1 alcalina. Ya +ue la# eacci%ne# #%n e'e #i5le#/ .a1 +ue em$lea un e6ce#% (e alc%.%l. O R - C - OR
O CH3O

R"OH

H+ o HO-

R - C - O - R"

ROH
O

CH3CH2OH

H+ o HO-

CH3CH2O

CH3OH

Fi la eacci0n e# catali*a(a $% "ci(% $ue(e lle'a #e a ca5% en $ e#encia (e un "ci(% mine al c%m% G2FOA % GCl/ $e % #i e# catali*a(a $% una 5a#e/ e#ta #uele #e la 5a#e alc06i(% (el alc%.%l c% e#$%n(iente. 7a t an#e#te i&icaci0n a(em"# (e la# a$licaci%ne# #int4tica# en la in'e#ti!aci0n en el la5% at% i%/ #e u#a am$liamente en la $ e$a aci0n (e la &i5 a #int4tica c%n%ci(a c%m% )ac 0n. COM!"T"NCI#$ Fnte#i# (e acetat% (e 5encil%. Ca acte i*a e i(enti&ica el c%m$ue#t% #inteti*a(%. M#T"RI#L"$ % R"#CTI O$ REAC8IVOF 8u5%# (e en#a1% 3 a(illa# BeaIe 6 2B0 m7 Em5u(%# Da$el (e &ilt % Di$eta# ;ec.e % 8 $%(e Re2illa Ba!ueta# ;A8ERIA7EF Acetat% (e etil% Alc%.%l 5encilic% A!ua (e#tila(a Pci(% #ul&- ic% c%ncent a(% n-.e6an% C %mat%&%li%# Ca$ila e# Cu5a c %mat%! "&ica I%(% met"lic%

2= F-CV3-3B-2

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!ROC"DIMI"NTO Transesterificacin.- En un tu5% (e $ ue5a c%l%ca = m7 (e acetat% (e etil%/ 1 lue!% a(ici%na alc%.%l 5enclic% 0/B m7. ;e*cla 1 a(ici%na 3 a A !%ta# (e "ci(% #ul&- ic% c%ncent a(%. ;e*cla c%n cui(a(% 1 c%l%ca el tu5% en un 5a,% ma ia >C0-70QC?. C %mat%! a&ia la# mue#t a# a l%# 0L/BL 1 =BL. Fa#e m0'il < n-.e6an%< acetat% (e etil% >2<= ' @ '? F%$% te < Filica!el 3 acti'a(% Re'ela(% < Va$% e# (e Y%(% met"lic% CU"$TION#RIO =. Inte $ ete l%# e#ulta(%# %5teni(%#. 2. Realice la ecuaci0n 1 #u mecani#m% (e eacci0n c% e#$%n(iente 3. El a %ma (e la# & uta# #e (e5e a la $ e#encia (e l%# e#te e#< menci%ne la c%m$%#ici0n +umica (e =0 a %ma# (e & uta# u %t %#.

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!RJCTIC# NB +N DERIVADOS DE COMPUESTOS CARBOXILICOS: AMIDAS SNTESIS DEL N!-"AMINOBENCEN#SUL$ONIL% N-"&-TIA'OL#ACETAMIDA INTRODUCCION
O NH2 7a# ami(a# tienen la e#t uctu a !ene al< El c%n%cimient% (e la +umica (e la# ami(a# e# mu1 im$% tante/ #%n (e ! an im$% tancia en 5i%+umica.. 7%# enlace# +ue #e unen a l%# amin%"ci(%# in(i'i(uale# $a a &% ma $ %tena# #%n $ inci$almente enlace# (e ti$% ami(a. 7a ma1% a (e la# ami(a# #%n #0li(a# a tem$e atu a am5iente. En el la5% at% i% #e $ e$a an ami(a# $% eacci0n ent e am%niac% % amina# c%n cl% u %#/ an.( i(%# (e "ci(%#/ e#te e# % "ci(%#. 7%# an.( i(%# 1 cl% u %# (e "ci(% eacci%nan 'i%lentamente c%n el am%niac% % amina a men%# +ue #e m%(e en la# eacci%ne# $% en& iamient%/ (iluci0n % me*cla# lenta# (e l%# c%m$ue#t%# eacci%nante#. In(u#t ialmente/ #e ac%#tum5 an $ e$a a $% calentamient% (e la# #ale# (e am%ni% (e "ci(%# ca 5%6lic%#. R

O R O R O

NH3

NH2 AMIDA

R-COOH

7a acilaci0n (e una amina e# una eacci0n "ci(%-5a#e (el ti$% (e 7eOi# en la +ue el ! u$% amin% 5"#ic% e&ect-a un ata+ue nucle%&lic% #%5 e el "t%m% (e ca 5%n% ca 5%nlic%/ +ue e# el cent % "ci(%. El ! u$% acil% uni(% a un "t%m% (e nit 0!en% tiene un e&ect% 9$ %tect% (el ! u$% amin%: cuan(% #e +uie e .ace eacci%ne# (e %6i(aci0n % .al%!enaci0n en el anill% a %m"tic% >amina# a %m"tica#?. COM!"T"NCI#$ Finteti*a el N-^A->Amin%5encen?Ful&%nil_ N->2-8ia*%l?Acetami(a Ca acte i*a e i(enti&ica el c%m$ue#t% #inteti*a(%.

M#T"RI#L"$ % M"TODO$ ;ate iale# 8u5%# (e en#a1% Di$eta# 3 a(illa# 23 F-CV3-3B-2

Reacti'%# N-^A->Amin%5encen?Ful&%nil_ 8ia*%l?Acetami(a An.( i(% ac4tic%

N->2-

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Balan*a analtica BeaIe 7"mina# $% ta%52et%# Ca$ila e# E#tu&a E+ui$% (e &ilt aci0n A!ua (e#tila(a Giel% Acetat% (e Etil% Y%(% Bencen% Pci(% #ul&- ic%

SNTESIS DEL N- !-"AMINOBENCEN#SUL$ONIL% N-"&-TIA'OL#ACETAMIDA !ROC"DIMI"NTO En un tu5% (e en#a1% lim$i% 1 #ec% c%l%ca A-Amin%-N-2-8ia*%lil5encenFul&%nami(a >=00 m!? 1 lue!% a,a(i an.( i(% ac4tic% >0.A ml? en& ian(% la me*cla a! e!a "ci(% #ul&- ic% c%ncent a(% >II a III !%ta#? .a#ta (i#%l'e / a!ita $% B minut%# 1 lue!% (e2a en e$%#% en un 5a,% (e .iel%/ &ilt a 1 !ua (a el $ %(uct%. I(enti&ica l% $% c %mat%! a&a en ca$a &ina. FODOR8E< Filica!el 3 FAFE ;OVI7< Acetat% (e etil% - Bencen% REVE7A)OR< Y%(% met"lic%
O H2N SO2NH N S H3C

+
H3C

O O

H2SO4

CH3COOH

+
S N

CH3-CO-HN

SO2NH

CUEF8IONARIO =.- D %$%n!a un mecani#m% (e eacci0n $a a la #nte#i# eali*a(a en la $ "ctica. 2.- ;enci%ne cuale# #%n la# acti'i(a(e# &a mac%l0!ica# (e la# #ul&a#. 3.- E#c i5a la e#t uctu a +umica (e %t a# #ul&a# in(ican(% cual e# el ! u$% &unci%nal +ue le (a acci0n &a mac%l0!ica.

!RJCTIC# NB ++ 2A F-CV3-3B-2 REV. JUNIO 2007

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D"RI #DO$ D" COM!U"$TO$ C#R'OECLICO$2 R"#CCION"$ D" "$T"RIFIC#CIN 0 $#!ONIFIC#CIN INTRODUCCION El Ja50n e# un a!ente lim$ia(% +ue #e &a5 ica utili*an(% ! a#a# 'e!etale# 1 animale# 1 aceite#. Qumicamente/ e# el ca 5%6ilat% (e #%(i% % la #al (e #%(i% % $%ta#i% (e "ci(% ! a#% +ue #e &% ma $% la eacci0n (e la# ! a#a# 1 aceite# c%n un "lcali. HISTO IA !" #A $A% ICACIO& !" 'A%(& 7%# & ance#e# (e#a %lla %n un m4t%(% $a a la &a5 icaci0n (el 2a50n utili*an(% el aceite (e %li'a en lu!a (e ! a#a# animale#. Gacia el a,% =B00/ int %(u2e %n #u# (e#cu5 imient%# en In!late a. E#ta in(u#t ia c eci0 "$i(amente en e#e $a# 1 en =C22 el e1 Jac%5% I le c%nce(i0 cie t%# $ i'ile!i%# al 2a50n. En =783/ el +umic% #uec% Ca l Nil.elm Fc.eele #imul% (e &% ma acci(ental la eacci0n +ue #e $ %(uce .%1 en el $ %ce#% (e .e 'i(% en la &a5 icaci0n (el 2a50n/ cuan(% el aceite (e %li'a/ .e 'i(% c%n 06i(% (e $l%m%/ $ %(uce una #u#tancia (ulce +ue 4l (en%min% Ol#u#/ $e % +ue .%1 #e c%n%ce c%m% !lice ina. COM!"T"NCI#$ El e#tu(iante $ e$a a a 2a50n a $a ti (e una eacci0n +umica (e ! a#a# e .i( 06i(% (e #%(i%. M#T"RI#L % R"#CTI O$ ;A8ERIA7EF Va#%# (e $ eci$ita(%# (e 200 ml Va#%# (e $ eci$ita(%# (e =00 ml A!ita(% Ba!ueta# 8ela (e a#5e#t% ;ec.e % (e 5un#en Da$el alumini% t i$%(e

REAC8IVOF Gi( 06i(% (e #%(i% Cl% u % (e #%(i% 3lice ina 3 a#a % aceite F a!ancia

$#!ONIFIC#CIN D" UN# IR#$# =.- C%l%ca =0! (e aceite % ! a#a en un 'a#% (e =00ml 1 $ %ce(e c%n $ ecauci0n a &un(i l%# c%n el mec.e % a &ue!% lent%. 2.- D e$a a una (i#%luci0n (e .i( 06i(% (e #%(i% >=0! (e .i( 06i(% (e #%(i% en 20ml (e a!ua?. A! e!ue $%c% a $%c% la (i#%luci0n a la ! a#a &un(i(a. 3.- A!ita 'i!% %#amente la me*cla 1 c%ntin-a el calentamient% .a#ta +ue (e#a$a e*can l%# ! um%# (e ! a#a. An%ta tu# %5#e 'aci%ne#. 2B F-CV3-3B-2 REV. JUNIO 2007

QUMICA ORGANICA 2014

A.-Vie te la me*cla en un 'a#% (e $ eci$ita(%# +ue c%nten!a 20! (e cl% u % (e #%(i% (i#uelt% en =00ml (e a!ua. C%l%ca la me*cla en un 5a,% (e .iel% 1 a!ite (e mane a c%ntinua. B.-)e2a e$%#a la me*cla $% =Bminut%# 1 #e$a a la me*cla $% (ecantaci0n 1 &ilt aci0n. C.-8%ma 8! (e 2a50n 1 m4*clal%# c%n Aml (e !lice ina 1 =0ml (e a!ua. Calienta la me*cla a &ue!% lent% (e2an(% en &% ma c%n#tante .a#ta l%! a una c%n#i#tencia .%m%!4nea. 7.-)e2a en& ia el $ %(uct% &inal 1 ante# (e +ue #e #%li(i&i+ue/ a! e!a una !%ta (e & a!ancia. CU"$TION#RIO =.- E6$lica l% #i!uiente. a?`Da a +u4 #e a! e!a el cl% u % (e #%(i% una 'e* +ue #e &% ma el 2a50na 5? `Que #u#tancia# +ue(an en el e#i(u% l+ui(% cuan(% #e &% ma el 2a50na. c?`C%ntiene el 2a50n e#t%# (e la 5a#e> NaOG ? utili*a(% en el $ %ce#%a 2.-In'e#ti!a +ue %t %# in! e(iente# #e a,a(en en l%# 2a5%ne# c%me ciale# 1 `$% +u4 a

!R#CTIC# NB +4 COM!U"$TO$ C#R'OEILICO$2 #N-CDRIDO$ D" JCIDO 2C F-CV3-3B-2 REV. JUNIO 2007

QUMICA ORGANICA 2014

-IDRLI$I$ D"L #N-CDRIDO M#L"ICO INTRODUCCION 7%# an.( i(%# tienen $unt%# (e e5ullici0n m"# ele'a(%# +ue #u# e#$ecti'%# "ci(%#. D% .i( 0li#i# $ %(ucen l%# e#$ecti'%# "ci(%#. COM!"T"NCI#$ Finteti*a el an.( i(% #uccnic% Ca acte i*a e i(enti&ica el an.( i(% #uccnic% me(iante eacci%ne# e#$eci&ica#. M#T"RI#L % R"#CTI O$ ;A8ERIA7EF 8u5%# (e en#a1% 3 a(illa# Di$eta# BeaIe E#$"tula# ;ec.e % 8 $%(e Re2illa (e a#5e#t%

REAC8IVOF An.( i(% maleic% GCl Acet%na Bencen% Ana an2a(% (e metil% Y%(% met"lic% Filica!el 3C0

-IDRLI$I$ D"L #N-CDRIDO M#L"ICO DROCE)I;IEN8O De#a An.( i(% maleic% >=00 m!? a(ici%na le a!ua (e#tila(a >3 m7? 1 GCl c%ncent a(% >0.= m7? a!ita c%n cui(a(% $% =0 min. 7ue!% anali*a $% c %mat%! a&a en ca$a &ina $a a c%m$ %5a la a$e tu a (el an.( i(% a "ci(% maleic%. Fa#e e#taci%na ia< Filica!el 3C0 Fa#e m0'il< Acet%na T 5encen% >=<= '@'? Re'ela(% < F%luci0n (e ana an2a(% (e metil% Fi el e#ulta(% e# $%#iti'% eali*a el #i!uiente en#a1%< CONVERFI[N )E7 PCI)O ;A7EICO EN PCI)O FU;ARICO A la #%luci0n ante# %5teni(a a,a(i GCl c%ncent a(% >0.3 m7? calenta / me2% e&lui / $% 20 min. A 70Q - 80QC/ en& ia la #%luci0n/ anali*a el $ %(uct% $% c %mat%! a&a en ca$a &ina. Fi n% c i#tali*a el $ %(uct% e'a$% a la #%luci0n. Fa#e e#taci%na ia< Filica!el 3C0 Fa#e m0'il< Acet%na T 5encen% >3<= '@'? Re'ela(% < F%luci0n (e ana an2a(% (e metil%

27 F-CV3-3B-2

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O C O CH2 ClH OH2 O HO C CH2 ClH OH2 O HO C CH2 CH2 C O cido !marico OH

C CH2 O Anhidrido maleico

HO C CH2 O cido maleico

CU"$TION#RIO =. Inte $ ete l%# e#ulta(%# %5teni(%#. 2. Realice la ecuaci0n 1 #u mecani#m% (e acci0n c% e#$%n(iente

!RJCTIC# NB +. 28 F-CV3-3B-2 REV. JUNIO 2007

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$CNT"$I$ CON !#RTICI!#CIN D" IRU!O$ "CINO$ INTRODUCCIN Fe .a c%n#i(e a(% e2em$l%# (e #u#tituci0n nucle%&lica en l%# +ue el eacti'% >nucle%&lic%? 1 el #u#t at% >elect 0&il%? #%n c%m$ue#t%# (i&e ente#. E#ta# eacci%ne# (e #u#tituci0n #%n la# FN= 1 la FN2. N% t%(a# la# eacci%ne# (e #u#tituci0n nucle%&lica #e 'e i&ican c%n acemi*aci0n >FN=? % in'e #i0n (e c%n&i!u aci0n >FN2?. 7a #u#tituci0n nucle%&lica $ue(e #e tam5i4n un $ %ce#% int am%lecula cuan(% el nucle0&il% 1 el ! u$% #aliente &% man $a te (e la mi#ma m%l4cula/ l% +ue % i!ina l%# llama(%# e&ect%# (e l%# ! u$%# 'ecin%#. 7a $a tici$aci0n (e l%# ! u$%# 'ecin%# $ e#entan l%# #i!euiente# e&ect%#< -7a 'el%ci(a( (e eacci0n aumenta< a1u(a an+uim4e ica. -El ca "cte e#te e%+umic%< el $ %(uct% +ue #e &% ma $ e#enta c%n&i!u aci0n eteni(a. -Due(e c%n(uci a un e% (enamient% m%lcula % t an#$%#ici0n m%lecula . El $%#i5le mecani#m% (e eacci0n $ue(e #e < 3 C C N 3K 2V 2N K C C
-

3 CC V

O'("TI O$2 Fineteti*a el "ci(% amin%etan%ic% me(iante la $a tici$aci0n (e ! u$%# 'ecin%#. Ca acte i*a e i(enti&ica el "ci(% amin%etan%ic% #inteti*a(% MATERIALES ( METODOS ;ate iale# 8u5%# (e en#a1% Di$eta# Balan*a analtica BeaIe =B0ml Da$el NGA88;ANN Ca$ila e# E#tu&a 3 a(illa# E#$"tula#

Reacti'%# A!ua (e#tila(a Etan%l Pci(% 5 %m% ac4tic% Gi( 06i(% (e am%ni% Nin.i( ina.

SNTESIS DEL )CIDO 2E F-CV3-3B-2

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PROCEDIMIENTO En un eci$iente lim$i% 1 #ec% c%l%ca (e 20 m! (e "ci(% 5 %m% ac4tic% a,a(i A ml (e am%niac% c%ncent a(% 1 lue!% B ml (e etan%l/ ce an(% el & a#c% .e m4ticamente a!ita c%n#tantemente (u ante =0 minut%#. I(enti&ica el $ %(uct% me(iante c %mat%! a&a en $a$el. Fa#e e#taci%na ia< Da$el O.attman Fa#e m0'il< EtOG-G O-NG OG 2BR >=.A - 0/A - 0/2? Re'eela(% < Nin.i( ina.
CH2 - COOH CIDO

NH3

#tOH

CH2 - COOH

"rH

"r - "ROMO #$ANOICO

NH2 CIDO - AMINO#$ANOICO

!RJCTIC# NB +8

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R"ORD"N#MI"NTO$ MOL"CUL#R"$O'T"NCIN D" L# '"N,OF"NON OEIM#)0 O'T"NCIN D" L# '"N,#NILID# INTRODUCCIN Fe .a c%n#i(e a(% e2em$l%# (e #u#tituci0n nucle0&ila en l%# +ue el eacti'% >nucle0&il%? 1 el #u#t at% >elect 0&il%? #%n c%m$ue#t%# (i&e ente#. E#ta# eacci%ne# (e #u#tituci0n #%n la# FN= 1 la FN2. N% t%(a# la# eacci%ne# (e #u#tituci0n nucle%&lica #e 'e i&ican c%n acemi*aci0n >FN=? % in'e #i0n (e c%n&i!u aci0n >FN2?. 7a #u#tituci0n nucle0&ila $ue(e #e tam5i4n un $ %ce#% int am%lecula cuan(% el nucle0&il% 1 el ! u$% #aliente &% man $a te (e la mi#ma m%l4cula/ l% +ue % i!ina l%# llama(%# e&ect%# (e l%# ! u$%# 'ecin%#. 7a $a tici$aci0n (e l%# ! u$%# 'ecin%# $ e#entan l%# #i!uiente# e&ect%#< -7a 'el%ci(a( (e eacci0n aumenta< a1u(a an+uim4 ica. -El ca "cte e#te e%+umic%< el $ %(uct% +ue #e &% ma $ e#enta c%n&i!u aci0n eteni(a. -Due(e c%n(uci a un e% (enamient% m%lecula % t an#$%#ici0n m%lecula . El $%#i5le mecani#m% (e eacci0n $ue(e #e < 3 C C N 3K 2V 2N K C C
-

3 CC

El e% (enamient% (e BecImann #i 'e $a a %5tene ami(a#. Fe $ %(uce en la# %6ima# lineale# % cclica#/ e#te e% (enamient% e# catali*a(% c%n "ci(% #ul&- ic%/ $entacl% u % (e &0#&% % % cl% u % (e t%#il%. )e#(e el $unt% (e 'i#ta e#te e %+umic% el ! u$% +ue mi! a e# a+uel +ue #e encuent a %$ue#t% al %6i( il%. En la# %6ima# cclica# el ! u$% +ue #e t an#$%ne e# !ene almente el mba# '%lumin%#% 1 %$ue#t% al %6i( il%/ #e &% ma una lactama c%n e6$an#i0n (e anill%.
R R C%N OH

R C%N R Intermedio

OH2

O&IMA

3= F-CV3-3B-2

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CH3 CH3 N OH H
+

OH2

El cati0n &% ma(% eci5e a una m%l4cula (e a!ua

CH3 N

CH3 +

OH2

NH O

7actama Al!un%# anti5i0tic%# c%m% la e it %micina +ue tiene un ! u$% ca 5%nil% C-E/ .a #e 'i(% $a a %5tene l%# (en%mina(%# mac %li(%# anti5i0tic%# c%n me2% acti'i(a( +ue #u $ ecu #% . COMPETENCIA C%n%ce 1 e6$lica la #nte#i# (e la Ben*anili(a $% e% (enamient% m%lecula Ca acte i*a e i(enti&ica el $ %(uct% &% ma(% ;A8ERIA7EF Y REAC8IVOF ;A8ERIA7EF E+ui$% (e e&lu2% Di$eta# 8u5%# (e en#a1% 3 a(illa# ;ec.e % 8 $%(e Re2illa (e a#5e#t% BeaIe E#$"tula# Em5u(%# Da$el (e &ilt % REAC8IVOF Ben*%&en%na Alc%.%l etlic% Cl% .i( at% (e Gi( %6ilamina A!ua (e#tila(a Acetat% (e #%(i% cte etlic% Pci(% #ul&- ic% c%ncent a(% Cl% %&% m% ;etan%l Filica!el 3 Y%(% met"lic%

OBTENCI*N DE LA BEN'O$ENON OXIMA DROCE)I;IEN8O En un #i#tema (e e&lu2% #e $%ne Ben*%&en%na >0/B !? (i#uelt% en alc%.%l >C m7?m"# una #%luci0n & a (e cl% .i( at% (e Gi( %6ilamina >0/7 !? (i#uelt% en a!ua (e#tila(a >2 m7? 1 acetat% (e #%(i% >= !? (i#uelt% en a!ua >= m7? #%mete la me*cla a e&lu2% $% 20 min. 32 F-CV3-3B-2 REV. JUNIO 2007

QUMICA ORGANICA 2014

Da#a la me*cla a un BeaIe 1 a! e!a (e B T =0 m7 (e a!ua $%ne en e$%#%/ el $ %(uct% #0li(% &ilt a 1 !ua (a . O'T"NCIN D" L# '"N,#NILID# 7a %6ima #inteti*a(a >=00 m7? #e $%ne en 4te etlic% >2 m7? en un eci$iente c%m$letamente #ec% 1 lue!% #e a! e!a !%ta# (e "ci(% #ul&- ic% c%ncent a(%/ calenta en B; $% =0 min. I(enti&ica el $ %(uct% me(iante c %mat%! a&a en ca$a &ina< Fi#tema (e #%l'ente< Cl% %&% m%-metan%l >=<= '@'? Re'ela(% < Va$% e# (e Y%(% met"lic% Fa#e e#taci%na ia< Filica!el 3C0

33 F-CV3-3B-2

REV. JUNIO 2007