Name: Shamaya Murray ID No: 28120661 Course: Organic Chemistry Lecturer: Jason Bac! Date: May"0# 2016 $ite: I%enti&ication o& &unctiona grou's (im: Systematicay i%enti&y the &unctiona grou's in the gi)en organic com'oun% an% 'er&orm the con&irmatory tests a&ter i%enti&ying the &unctiona grou's* (+stract: ( &unctiona grou' is a 'ortion o& a moecue that is a recogni,a+e-cassi&ie% grou' o& +oun% atoms* In organic chemistry it is )ery common to see moecues co m'rise% mainy o& a car+on +ac!+one .ith &unctiona grou's attache% to the chain* $he aim o& the e/'eriment is to systematicay i%enti&y the &unctiona grou's in the gi)en organic com'oun% an% 'er&orm the con&irmatory tests a&ter i%enti&ying the &unctiona grou's* $he 'roce%ure can +e seen as outine% in the a+ manua* It can +e concu%e% that %i&&erent &unctiona grou' .ere i%enti&y an% con&irmatory test %one*
(''aratus-Materias: Materias NaO Borches reagent e% itmus 'a'er NaCO" 4eC" Methano (coho 5n!no.n Su+stance Sch&&s reagent CL So%ium Nitrate
(''aratus $est tu+e Ice +ath 3ater +ath Dro''er
Intro%uction: ( &unctiona grou' is a 'ortion o& a moecue that is a recogni,a+e-cassi&ie% grou' o& +oun% atoms* In organic chemistry it is )ery common to see moecues co m'rise% mainy o& a car+on +ac!+one .ith &unctiona grou's attache% to the chain* $he &unctiona grou' gi)es the moecue its 'ro'erties# regar%ess o& .hat moecue contains it they are centres o& chemica reacti)ity* $he &unctiona grou's .ithin a moecue nee% to +e i%enti&ie% .hen naming* $he &oo.ing &unctiona grou's .i +e %iscusse% in this e/'eriment: (mi%es# (ci%s# 7henos# (%ehy%es-!etones# (%ehy%es# an% (mines* etones-a%ehy%es9a car+ono/ygen %ou+e +on%# .here the car+on is aso attache% to t.o other car+ons ;!etones< or to a car+on an% hy%rogen ;a%ehy%e<* etones an% a%ehy%es react .ith a chemica cae% 2#=%initro'henyhy%ra,ine ;2#=DN7< to &orm a yeo. or orange soi% .ithin a &e. minutes*
(mi%es are %eri)e% &rom car+o/yic aci%s* ( car+o/yic aci% contains the COO grou'# an% in an ami%e the O 'art o& that grou' is re'ace% +y an N2 grou'* So ami%es contain the CON2 grou'* ( car+o/yic aci% is an organic com'oun% that has a car+o/y grou'* $he car+o/y grou' is a &unctiona grou' that contains a car+on>o/ygen %ou+e +on% an% an O grou' aso attache% to the same car+on atom# +ut it has characteristic 'ro'erties o& its o.n* (s .ith a%ehy%es an% !etones# car+o/yic aci% &ormuas can +e .ritten to sho. the car+ontoo/ygen %ou+e +on% e/'icity# or the car+o/y grou' can +e .ritten in con%ense% &orm on one ine* In genera# car+o/yic aci%s are re'resente% +y the &ormua COO# .here is a hy%rocar+on g rou'*
(n amine is a com'oun% %eri)e% &rom ammonia ;N"< it has one# t.o# or a three o& the hy%rogen atoms o& N" re'ace% +y an a!y ;or an ary< grou'* Li!e N"# amines are .ea! +ases* $he &unctiona grou' o& an amine is a nitrogen atom .ith a one 'air o& eectrons an% .ith one# t.o# or three a!y or ary grou's attache%* ( hy%ro/y grou' is hy%rogen +on%e% to o/ygen that is co)aenty +on%e% to the rest o& the moecue* Just as .ith a!enes# a!ynes# an% ! etones# the ocation o& the hy%ro/y grou' is ma%e +y num+ering the moecue such that the hy%ro/y grou' has the o.est num+er 'ossi+e* eagents use% in the e/'eriment: Schi&&s an% Borsches reagent* Schi&&?s reagent is a chemica 're'aration use% to test a soution &or the 'resence o& a%ehy%es* It is com'ose% o& rosaniine an% su&urous aci% %isso)e% in .ater* 3hen the reagent is a%%e% to a soution that contains a%ehy%es# it turns +right 'in! in coour* (ction o& Borsche?s eagent: (%ehy%es reacts .ith 2#= %initro'heny hy%ra,ine soution to gi)e a orange-re% 'reci'itate o& a%ehy%e 2#= %intro'henyhy%ra,one %eri)ati)e*
Metho%oogy: (s outine% in the a+ manua* esuts: $a+e sho.ing %i&&erent &unctiona grou's* 4unctiona grou'
5n!no.n su+stance @
O+ser)ation
(mi%es
reagents 5n!no.n su+stance@ NaO
e% itmus 'a'er %i% not change to +ue a+sence o&
(ci%s
5n!no.n su+stance @
ami%es No coour change > a+sence o&
7henos
NaCO" 5n!no.n su+stance @
aci% No )ioet cooyration a+sence
(%ehy%es-!etones
(coho@4cC" 5n!no.n su+stance @
o& 'henos ( yeo. ''t 'rensence o&
(%ehy%es
methano@+orsches 5n!no.n su+stance @ schi&&s
a%ehy%es-!etones Aioent coour %e)eo' .ithin 2 minutes > 'resence o&
(mines
5n!no.n su+stance @CL@
a%ehy%es No ra'i% &oaming > a+sence o&
So%ium Nitrate
amines
Discussion: In this e/'eriment +ecause &unctiona grou's in&uence the 'hysica# chemica# an% s'ectra 'ro'erties o& an organic com'oun%# the i%enti&ication o& a com'oun%?s &unctiona grou's +y measuring certain 'hysica 'ro'erties# o+ser)ing its chemica +eha)ior .ith %i&&erent cassi&ication reagents# an% stu%ying other s'ectra %ata*
3hat .i &oo. is a series o& reaction that ha''ene% .hen each &unctiona grou' .as teste%*
eactions o& ami%es: eaction o& NaO: (mi%es are %ecom'ose% +y NaO to e)o)e ammonia* $he gas can +e teste% +y a moist re% itmus 'a'er .hich is then turne% +ue*
•
(!aine hy%roysis o& aromatic ami%es to aromatic aci%:
$he sou+e so%ium sat o& aromatic aci% &orme% &rom aromatic ami%es u'on hy%roysis is regenerate% as .hite 'reci'itate in aci%ic me%ium*
•
Biuret eaction &or ai'hatic %iami%e:
3hen ai'hatic %iami%e is heate% at a tem'erature a+o)e its meting 'oint# ammonia is e)o)e% an% crystaine +iuret is &orme%* $his +iuret in a!aine me%ium gi)es a )ioet coour .ith a %ro' o& co''er su'hate soution*
Biuret reaction
•
y%ro/amic aci% test &or aromatic 'rimary ami%es:
y%rogen 'ero/i%e reacts .ith aromatic 'rimary ami%es to &orm the hy%ro/amic aci%# .hich then reacts .ith &erric chori%e to &orm &erric hy%ro/amate com'e/ ha)ing a )ioet coour*
eactions o& car+o/yic aci%s:
•
eaction .ith NaO:
Car+o/yic aci%s +eing aci%ic %isso)es in NaO to &orm so%ium sat*
•
eaction o& NaCO":
4orms sat .ith so%ium +icar+onate soution .ith the e)oution o& car+on %io/i%e*
•
4uorescein eaction:
$he anhy%ri%es o& aromatic 1#2%icar+o/yic aci%s on heating .ith resorcino gi)es a %ye &uorescein* $his %ye in NaO soution gi)es a yeo.ish re% soution .ith green &uorescence*
eactions o& 'henos:
•
eaction o& neutra &erric chori%e soution:
7heno &orm characteristic cooure% iron com'e/es .hen treate% .ith neutra &erric chori%e soution* *g* 'heno resorcino ) ioet coour# catechogreen etc*
•
(,o %ye &ormation:
(ry%ia,onium sats react .ith aromatic rings o& 'henos to &orm highy cooure% a,o com'oun%s* $hese reactions are cae% cou'ing reac tions*
•
Ben,oyation:
7henos react .ith +en,oy chori%e in 'resence o& NaO# to &orm esters*
eactions o& 'rimary amines:
•
Dia,otisation:
(t o. tem'erature ;0oC< aromatic 'rimary amines %isso)e% in strong aci%s ;C 2SO=< reacts .ith nitrous aci% ;NaNO2 @C< to &orm .ater sou+e %ia,onium sats* (i'hatic 'rimary amines %o not &orm sta+e %ia,onium sats un%er simiar con%ition* $hey react .ith nitrous aci% to yie% acohos an% nitrogen ;causes ra'i% &oaming<*
•
(,o %ye &ormation &or aromatic 'rimary amines:
(ry%ia,onium sats react .ith aromatic rings o& 'henos to &orm highy cooure% a,o com'oun%s* $hese reactions are cae% cou'ing reactions*
•
Ben,oyation:
7rimary aromatic amines react .ith +en,oy chori%e in 'resence o& NaO# re'acing the atom attache% to the N atom .ith the +en,oy grou' to gi)e anii%es*
•
ins+erg reaction:
ins+erg reagent is cae% +en,enesu&ony chori%e* 7rimary ai'hatic amines on reaction .ith +en,enesu&ony chori%e NaO gi)es Na!ysu'honami%e .hich contains an aci%ic hy%rogen an% hence %isso)e in NaO soution to &orm the sou+e so%ium sat* $he soution thus o+taine% on aci%i&ication gi)es a 'reci'itate o& &ree su&onami%e .hich is insou+e in C*
eactions o& a%ehy%es:
(ction o& Schi&&s reagent:
Schi&&s reagent is a re% soution o& rosaniine hy%rochori%e %isso)e% in .ater .hich is %ecoourise%
+y
'assing
su'hur
%io/i%e*
Diute soutions o& a%ehy%es .hen a%%e% to Schi&&s reagent restores its re% coour so.y*
(ction o& Borsches eagent:
(%ehy%es reacts .ith 2#=%initro'heny hy%ra,ine soution to gi)e a orange-re% 'reci'itate o& a%ehy%e 2#=%intro'henyhy%ra,one %eri)ati)e*
eactions o& !etones:
(ction o& Borsches eagent:
etones reacts .ith 2# = %initro'heny hy%ra,ine soution to gi)e an orange-re% 'reci'itate o& !etone 2#= %intro'henyhy%ra,one %eri)ati)e*
Concusion: It can +e concu%e% that %i&&erent &unctiona grou' .ere i%enti&y an% con&irmatory test %one*
e&erences: )a+*amrita*e%u#* ;2011<* Detection o& 4unctiona Erou's* etrie)e% 1 June 2016# &rom )a+*amrita*e%u-Fsu+G2+rchG1H1simG"=cntG1 Soomons# 4ryhe* Organic Chemistry# 8th %ition 3ieyIn%ia# 2006* $he systematic i%enti&ication o& organic com'oun%s +y a'h L Shriner 8th e%ition 4re%eric! Eeorge Mann# Bernar% Chares Saun%ers# 7ractica organic chemistry* 1H60
