CLASSIFICATION TESTS FOR HYDROXYL- AND CARBONYL-CONTAINING COMPOUNDS Pia Lorraine F. San Luis, Michelle Joy G. Sia, Paulene Stephanie A. Soriano, Trisha Joy M. Taas, Lara Monique S. Tuazon and Michelle V. Yu Group !" #ioche$istry %r&anic "he$istry La'oratory
ABSTRACT This e(peri$ent ai$ed to distin&uish )hether a co$pound is hydro(yl* or car'onyl*containin&. car'onyl*containin&. This is done to di++erentiate the three types o+ alcohols and di++erentiate aldehydes +ro$ etones. -t also ai$ed to e(plain the $echanis$s inoled in the di++erentiatin& tests. -n this e(peri$ent, there are seeral di++erentiatin& tests done usin& di++erent sa$ples such as/ n*'utyl alcohol, sec*'utyl alcohol, tert*'utyl alcohol, Acetaldehyde, n*'utyraldehyde, n*'utyraldehyde, #enzaldehyde, Acetone, Acetophenone and -sopropyl alcohol. The tests include the +ollo)in&/ solu'ility o+ alcohols in )ater, Lucas test, "hro$ic Acid Test Test 0Jones %(idation1, !,2*dinitrophenylhydrazone 0or !,2*34P1 Test, Fehlin&5s Test, Tollens5 Siler Mirror Test and -odo+or$ Test. -n the solu'ility o+ alcohols in )ater n*'utyl alcohol, sec*'utyl alcohol, tert*'utyl alcohol )ere $isci'le in )ater and only 'enzzyl alcohol )as i$$isci'le. 6sin& Lucas test to di++erentiate the pri$ary, secondary, and tertiary alcohols, there )as no chan&e in n*'utyl alcohol and the solution turns tur'id in 'oth sec* 'utyl alcohol and tert*'utyl tert*'utyl alcohol. Moreoer, Moreoer, the tur'idity is due to the alyl chloride chloride +or$ation. The "hro$ic Acid Test Test is +or co$pounds that possess o(idizin& or reducin& property and in the e(peri$ent, no chan&e in color happened in the test sa$ples. -n !,2*34P Test, conducted as con+ir$atory tests +or car'onyl car'onyl &roups and &ae &ae results results o+ yello) yello) oran&e oran&e precipita precipitate te +or acetaldeh acetaldehyde yde and acetone, acetone, oran&e oran&e precipitate +or 'enzaldehyde, and oran&e red precipitate +or acetophenone. Fehlin&5s Test and Tollens5 Siler Mirror Test are 'oth conducted to di++erentiate aldehydes and etones. -n Fehlin&5s Test, there )as no chan&e in the 'lue solution o+ 7etone )hile the 'lue solution o+ Aldehyde &ies a positie result o+ a 'ric red precipitate o+ cuprous o(ide. %n the other hand, in Tollens5 Siler Mirror Test, there )as no chan& chan&e e in the col colorl orless ess sol soluti ution on o+ 'enzal 'enzaldeh dehyde yde and aceto acetophe phenon none e )hile )hile the col colorl orless ess solut solution ion o+ acetaldehyde and acetone produces a siler $irror on the test tu'e. Lastly, -odo+or$ test &ies a positie result o+ a yello) precipitate only in acetone and isopropyl alcohol.
INTRODUCTION Alco Alcoho holl is one one o+ the the $ost $ost co$$ co$$on on or&a or&ani nic c co$pou co$pounds nds,, they they are )idely )idely used used in di++er di++erent ent industries. -t is a co$pound that has a hydro(yl &rou roup 'ond 'onded ed to a satur turated sp 8*hy'ridized car'on ato$, 9*%:. Alcohols are polar 'ecause o+ the hydro(yl &roup )hich allo)s alcohol to attract other $olecules throu&h hydro&en 'ondin& )hich is rela relate ted d to thei theirr a'il a'ilit ity y to incr increa ease se )ate )aterr solu'ility. ;<=
t)o 0di++e 0di++eren rentt or si$ila si$ilar1 r1 alyl alyl &roups &roups.. ?hile ?hile tertiary alcohols are alcohols attached directly to three alyl &roups. ;!=
Fi!"r# %. Types o+ alcohol. Fi!" Fi!"r# r#
$.
Stru Struct ctur ure e
o+
alcohols.
Alco Alcoho hols ls can can 'e clas classi si+ie +ied d as pri$ pri$ar ary y, seco second ndar ary y or tert tertia iary ry depe depend ndin in& & on ho) ho) the the hydro(yl &roup 0*%:1 is 'onded to the car'ons. Pri$ary alcohols are alcohols in )hich the *%: is 'ond 'onded ed to a sin& sin&le le aly alyll &rou &roup> p> on the the othe otherr hand, secondary alcohols are attached directly to
Aldehyde is a car'onyl*+unctional car'onyl*+unctional &roup that is 'onded to a hydro&en ato$ )hile a etone is a +uncti +unctiona onall &roup &roup that that is 'onded 'onded to t)o car'o car'on n ato$s. ato $s. #ot #oth h +unction +unctional al &roups &roups are polar polar that that inte intera ract cts s )ith )ith dipol dipole* e*di dipo pole le inte intera ract ctio ion. n. This This resu result lts s to a hi&h hi&her er 'oil 'oilin in& & poin pointt than than thos those e nonpolar co$pounds. ;8=
Lucas test, "hro$ic "hro$ic Acid Test, est, !,2*34 !,2*34P P test, test, Fehli Fehlin&5 n&5s s Test, st,T Tollens5 llens5 Sile Silerr Mirror Mirror test test and -odo+or$ test )ere the test used in the e(peri$ent. Lucas Lucas rea&ent rea&ent is a solution solution o+ concentra concentrated ted hydrochl hydrochloric oric acid and anhydrou anhydrous s zinc chloride. chloride. This is used as a rea&ent in Lucas test. This test is used to deter$ine the type o+ alcohol 'ased on reactiity. The reaction that occurs in the Lucas test est is an S4< nucle nucleoph ophill illic ic reacti reaction. on. The acid acid catalyst actiates the %: &roup o+ the alcohol 'y protonatin& the o(y&en ato$. The 'ond 'reas to &ene &enera rate te a car' car'oc ocat atio ion n cati cation on )hic )hich h in turn turns s reacts to chloride +or$in& an alyl halide product. ;2= The The chro$ chro$ic ic a acid cid test test is a test test +or +or pri$ pri$ary ary,, secondar secondary y alcohols alcohols and aldehyde. aldehyde. A 'lue*&reen 'lue*&reen lay layer indi indica cate tes s a posi positi tie e test test.. -n this this test test,, pri$a pri$ary ry alcoho alcohols ls and aldehy aldehyde de are are o(idiz o(idized ed to car'o car'o(y (ylic lic acids acids )hile )hile alcoho alcohols ls are are o(idi o(idized zed to @ etones and the "r ions are reduced to "r 8. ;B=
acidic and )ill react )ith 'ase to +or$ the anion, )hich then reacts )ith iodine to +or$ an alpha* iodo etone. -n a $ethyl etone, all three alpha hydro&ens are su'stituted 'y iodine in this )ay to +or$ the triiodo co$pound, )hich then reacts )ith $ore 'ase to +or$ the car'o(ylic acid salt plus iodo+or$, a yello) precipitate. For$ation o+ a yello) precipitate there+ore indicates the presence o+ a $ethyl &roup directly attached to the car'onyl. ;@=
EXPERIMENTAL A. Sa&'(#s "s#) The sa$ples used in the e(peri$ent )ere ethanol, n*'utyl alcohol, sec*'utyl alcohol, tert* 'utyl alcohol, 'enzyl alcohol, n*'utyraldehyde, 'enzaldehyde, acetone, acetophenone, isopropyl alcohol, and acetaldehyde.
B. Pro*#)"r# $. So("+i(i,y o A(*oho(s i /a,#r
The The !,2* !,2*di dini nitr trop ophe heny nylh lhyd ydra razo zone ne test test is per+ per+or or$e $ed d to dete deter$ r$in ine e the the pres presen ence ce o+ a car'onyl &roup0etone and aldehyde1. -t is also a deriatie +or$ation. +or$ation. -t reacts to +or$ a solid !,2* dinitr dinitroph opheny enylhy lhydr drazo azone ne 034P1 034P1 deria deriati tie. e. The color i$parted &ies us a structural in+or$ation. Posit Positie ie result result +or this test test is the +or$at +or$ation ion o+ yello yello) ) oran oran&e &e precip precipita itate. te. -+ the precip precipita itate te produc produced ed is yello) yello),, it $eans $eans that that the car'o car'ony nyll &rou roup in the unn nno)n o)n is uncon nconCu Cu&a &ate ted. d. A reddish*oran&e color $ost liely $eans that the car'onyl &roup is conCu&ated. ;@=
Fie test tu'es )ere la'eled 0A*1, and < drops o+ each alcohols 0A*ethanol, #* n*'utyl alcohol, "* *'utyl alcohol, 3* tert *'utyl *'utyl alcohol, and * sec *'utyl 'enzyl alcohol1 )ere placed. < $L o+ )ater one drop at a ti$e )as added to each tu'e containin& the alcohols and the $i(ture )as shaen thorou&hly a+ter each addition. .!B $L o+ distilled )ater )as added at a ti$e )ith i&orous shain& )hen cloudiness )as o'sered. The total olu$e o+ )ater added )as noted. The solu'ility o+ alcohol in )ater )as )as deter$ined 'y o'serin& the results a+ter addin& !. $L )ater.
Fehlin&5 Fehlin&5s s test uses the +ehlin&5s +ehlin&5s solution, solution,a a $i(ture $i(ture o+ Fehlin&5 Fehlin&5s s A 0copper00copper0--1 -1 sul+ate1 sul+ate1 and Fehli ehlin& n&5s 5s # 0sod 0sodiu iu$ $ pota potass ssiu iu$ $ tart tartat ate e and and sodiu$ hydro(ide1, )hich is an o(idizin& a&ent. %nly aldehydes are o(idized to car'o(ylic acids and )ill reduce the cupric ion to cuprous o(ide. A positie result produces a 'ric red precipitate. ;D=
%. L"*as T#s,
Tollen5s Tollen5s test uses the Tollen5s Tollen5s rea&ent * 0A&04:81! E%: is a )ea o(idant only aldehydes )ill react in this test. Aldehydes )ill 'e o(idized to ca'o(ylic acids. As a result, it )ill produce a siler $irror )hich is the positie result. ;D= The iodo+or$ test indicates indicates the presence presence o+ an aldehyde or etone in )hich one o+ the &roups directly attached to the car'onyl car'on is a $ethyl &roup. -n the iodo+or$ test, the unno)n is allo)ed to react )ith a $i(ture o+ iodine and 'ase. :ydro&ens alpha to a car'onyl &roup are
Preparation o+ the rea&ent )as not needed, 'ecause it )as already prepared. A'out B $& 0!*8 drops1 o+ sa$ple )as added to < $L o+ the rea&ent in a s$all ial. The ial )as capped and shoo i&orously +or a +e) seconds. The $i(ture )as allo)ed to stand at roo$ te$perature. This test )as per+or$ed on n*'utyl alcohol, sec *'utyl *'utyl alcohol, and tert *'utyl *'utyl alcohol. For$ation o+ cloudy suspension or +or$ation o+ ! layers )as o'sered.
0. Chro&i* A*i) T#s, 1Jo#s O2i)a,io3 Preparation o+ the rea&ent )as not needed, 'ecause it )as already prepared. < drop o+ the liquid sa$ple )as dissoled in < $L o+ acetone in a s$all ial. B drops o+ chro$ic acid rea&ent )ere added, one drop at a ti$e, )hile shain& the $i(ture. The test tu'es )ere placed in @H "
)ater 'ath +or B $inutes. The color o+ each solution )as noted.
4. %54-)ii,ro'h#y(hy)ra6o# 1or %54-DNP3 T#s, Preparation Preparation o+ the rea&ent )as not needed, 'ecause it )as already prepared. 3rops o+ the liquid sa$ples )ere placed into +ie di++erent test tu'es. B drops o+ IB ethanol )as added to each. -t )as )ell shoo. 8 drops o+ !,2* dinitrophenylhydrazine dinitrophenylhydrazine )as added. The solutions )ere allo)ed to stand +or
For For the test +or solu'ili solu'ility ty o+ alcoho alcohols ls in )ater, er, the the tur' tur'id idit ity y o+ the the soluti lution ons s )as o'sered. The cloudiness o+ the solution $eans that the speci+ic alcohol is solu'le in )ater. The a$ount o+ )ater needed to produce a ho$o&enous dispersion )as also recorded.
Ta+(# $. Solu'ility o+ Alcohols in )ater.
A(*oho(
7. F#h(i!8s T#s, 9ea&ent )as $ade 'y $i(in& equal a$ounts o+ Fehlin&Ks A 0D & o+ hydrated copper 0--1 sul+ate dissoled in < $L o+ )ater1 and Fehlin&Ks # 08B & o+ potassiu$ sodiu$ tartrate and < & o+ 4a%: in < $L )ater1. < $L o+ +reshly prepared Fehlin&Ks rea&ent )as placed into each test tu'e. 8 drops o+ sa$ple )as added to 'e tested. The test tu'es )ere placed in a 'eaer o+ 'oilin& )ater and the chan&es occurred )ere o'sered )ithin <*
9. To((#s: Si(;#r Mirror T#s, Preparation Preparation o+ the rea&ent )as not needed, 'ecause it )as already prepared. Four test tu'es )ith < $L o+ +reshly prepared Tollens5 Tollens5 rea&ent )ere prepared. T)o drops o+ each sa$ple )ere added separately/ acetaldehyde, 'enzaldehyde, acetone, and acetophenone. The $i(tures )ere shoo and )ere allo)ed to stand +or < $inutes. The test tu'es )ere placed in a 'eaer o+ )ar$ )ater 08B*BH "1 +or B $inutes. %'serations )ere recorded.
<. Io)oor& T#s, T)o drops o+ each sa$ple 0acetaldehyde, 'enzaldehyde, acetone, acetophenone, and isopropyl alcohol1 )ere placed into its o)n test tu'e. ! drops o+ < 7- solution )as added. ?hile shain&, ! drops o+ +resh chlorine 'leach 0B sodiu$ hypochlorite1 )as added and $i(ed in each tu'e. For$ation o+ a yello) precipitate )as noted.
RESULTS AND DISCUSSION
E,hao( ":8":!%:
A&o", o =a,#r ##)#) ,o 'ro)"*# a ho&o!# o"s )is'#rsi o
So("+i( i,y i =a,#r
< drop
$isci'l e
-+",y( a(*oho(
@< drops
$isci'l e
s#*-+",y( a(*oho(
! drops
$isci'l e
,#r,-+",y( a(*oho(
2 drops
$isci'l e
8 $L
i$$isci 'le
B#6y( a(*oho(
As sho)n in the ta'le a'oe, only 'enzyl alcohol )as insolu'le in )ater )hile ethanol, n* 'utyl alcohol, sec*'utyl alcohol, tert*'utyl alcohol )ere all solu'le. This +ollo)s the principle lie dissoles lie and there+ore it can 'e said that the alcohols solu'le in )ater )ere polar co$pounds. The The Luc Lucas test test di++ di++er eren enti tia ated ted thre three e sa$p sa$ple les s na$e na$ely ly n*'u n*'uty tyll alco alcoho hol, l, sec* sec* 'uty 'utyll alcohol, and tert*'utyl alcohol. Ta'le ! presents the results o+ the Lucas test.
Ta+(# %. Lucas Test. S"+s,a*# -+",y( a(*oho(
R#a*,io o+s#r;#)
no chan&es
s#*-+",y( a(*oho(
tur'id
,#r,-+",y( a(*oho(
tur'id
Acco Accord rdin in& & to the the ta'l ta'le e a'o a'oe e n*'u n*'uty tyll alco alcoho holl is solu solu'l 'le e in Luca Lucas s rea& rea&en entt )hil )hile e a +or$ation o+ a cloudy layer )as o'sered in sec* 'utyl alcohol and tert*'utyl alcohol. #elo) is the che$ical equation +or this test/
As indica indicated ted in the ta'le, ta'le, aceta acetalde ldehyd hyde e and acetone produced a yello) oran&e precipitat precipitate, e, 'enzaldehy 'enzaldehyde de produced produced an oran&e oran&e precipitat precipitate, e, and only acetophen acetophenone one produced produced a red red oran oran&e &e prec precip ipit itat ate e )hic )hich h indi indica cate ted d the the pres presen ence ce o+ a car' car'on ony yl &rou &roup. p. #e #elo lo) ) is the the che$ical equation +or this test/
The The Fehl Fehlin in&K &Ks s test test and and Tollen llenKs Ks Sil Siler er $irr $irror or test test )ere )ere per+ per+or or$e $ed d to di++ di++er eren enti tiat ate e aldehy aldehydes des +ro$ +ro$ etone etones. s. -n the Fehli Fehlin&K n&Ks s test, test, aldehy aldehydes des &ae &ae a positi positie e result result o+ 'ric 'ric red precipi precipitate tate )hile etones did not produce any reaction. -n the TollenKs test, aldehydes )ere e(pected to 'e o(idized )hile etones did not under&o any o(idation.
Ta+(# 0. Fehlin&Ks Test and TollenKs Siler Mirror Test The "hr "hro$ic o$ic Acid Test is a tes test +or +or co$p co$pou ound nds s cont contai aini nin& n& o(id o(idiz izin in& & or redu reduci cin& n& proper property ty.. 4o color color chan&e chan&es s in all the sa$ple sa$ples s )ere )ere o'se o'ser red ed 'y the the anal analys ysts ts.. #elo #elo) ) is the the che$ical equation +or this test/
S"+s,a*# A*#,a()#hy)# B#6a()#hy)# A*#,o#
F#h(i!8s 'ric red precipitate no precipitate no precipitate
A*#,o'h#o#
no precipitate
To((#8s siler $irror precipitate no precipitate siler $irror precipitate no precipitate
As sho)n in the ta'le 'le a'oe, only aceta acetalde ldehy hyde de produc produced ed a 'ric 'ric red preci precipit pitate ate and in the TollenKs llenKs test test the acetal acetaldeh dehyde yde and aceto acetone ne produc produced ed a sile silerr $irror $irror precip precipita itate. te. #elo) are the che$ical equations +or these tests/ Fehlin&Ks test
The !,2*dinitrophenylhydrazone !,2*dinitrophenylhydrazone 0or !,2* 34P1 Test Test )as a con+ir$atory test +or the presence o+ car'onyl &roups. The +or$ation o+ a red oran&e precipitate &ies a positie result.
TollenKs test
Ta+(# %. !,2*34P Test. S"+s,a*# A*#,a()#hy)# B#6a()#hy)# A*#,o# A*#,o'h#o#
Co(or o Pr#*i'i,a,#s yello) oran&e oran&e yello) oran&e red oran&e
-n the -odo+or$ test $ethyl etones &ae a positie iodo+or$ test.
Ta+(# 4. -odo+or$ test. S"+s,a*# A*#,a()#hy)# -+",yra()#hy)# B#6a()#hy)# A*#,o# A*#,o'h#o# Iso'ro'y( a(*oho(
R#a*,io o+s#r;#) no yello) precipitate no yello) precipitate no yello) precipitate yello) precipitate no yello) precipitate yello) precipitate
Accordin& to the &ien ta'le, only acetone and isop isoprropyl opyl alco alcoh hol prod produc uced ed a yello) llo) precip precipita itate. te. #elo) #elo) is the che$ic che$ical al equati equation on +or this test/
REFERENCES ;<= Alcohol. 0n.d.1. 9etrieed 4oe$'er !, !<@, +ro$ https/EE))).'ritannica https/EE))) .'ritannica.co$EscienceEa .co$EscienceEalcohol lcohol ;!= An introduction to alcohols. 0n.d.1. 9etrieed 4oe$'er !, !<@, +ro$ http/EEche$&uide.co.uEor&anicpr http/EEche$&uide.c o.uEor&anicpropsEalcoholsE'a opsEalcoholsE'a c&round.ht$l
;8= Aldehydes and 7etones * 3u++erin*Peel "atholic 3istrict ... 0n.d.1. 9etrieed 4oe$'er !, !<@, +ro$ http/EE))).dpcds'.or&E49E http/EE))). dpcds'.or&E49ErdonlyresEI#@2F rdonlyresEI#@2F@* @* DDF*2DF*AB* F3FD#@I@"E<<@BBE
;B= Functional Groups * The "hro$ic Acid Test. 0n.d.1. 9etrieed 4oe$'er !, !<@, +ro$ http/EE))).harpercolle&e.eduEt$* psEch$E<Ed&oda$'eEthedisEqualEchro$ic.ht $ ;@= -denti+ication o+ an 6nno)n Alcohols, Aldehydes, and ... 0n.d.1. 9etrieed 4oe$'er !, !<@, +ro$ http/EE))).che$.u$ass.eduE http/EE))). che$.u$ass.eduENsa$alE!@IEa Nsa$alE!@IEaa.pd a.pd + ;D= ?riter, #. 0
