CLASSIFICATION TESTS FOR HYDROXYL AND CARBONYL CONTAINING COMPOUNDS Margarita Ysabel S. Mangahas, Cara Camille M.

Matute, Emilyn D. Millares, John Acener C. Pad a and Kathryn Cheshire P. Pangilinan Group 5 2 Medi!al "e!hnology #rgani! Chemistry $aboratory ABSTRACT
%ydro&yl and Carbonyl !ontaining samples 'ere tested in this e&periment. "he samples 'ere analy(ed through tests in)ol)ing the solubility

o* al!ohols in 'ater, $u!as test, Chromi! !id test, 2,+,Dinitrophenylhydra(one -2,+,D.P/ test,

0ehling1s test, "ollens1 Sil)er Mirror test, and 2odo*orm test. $u!as test di**erentiates primary, se!ondary and tertiary al!ohols. Chromi! test 'as per*ormed to 3no' i* the sample is o&idi(able. 2,+,Dinitrophenylhydra(one test 'as per*ormed *or aldehydes and 3etones. 0ehling1s "est and "ollens1 Sil)er Mirror "est are tests *or aldehydes. 2odo*orm test is a test *or methyl !arbinol and methyl!arbonyl groups. "he samples are n,butyl al!ohol, sec,butyl al!ohol, tert, butyl al!ohol, a!etaldehyde, n,butylaldehyde, ben(andehyde, a!etone, and isopropyl al!ohol.

INTRODUCTION
%ydro&yl group is used to des!ribe the *un!tional group 4#% 'hen it is a substituent in an organi! !ompound. 5+6 7epresentati)e organi! mole!ules !ontaining a hydro&yl group are 3no'n as al!ohols. %ydro&yl groups are espe!ially important in biologi!al !hemistry be!ause o* their tenden!y to *orm hydrogen bonds both as donor and a!!eptor. "his property is also related to their ability to in!rease hydrophili!ity and 'ater solubility 586. "here are three !lassi*i!ations o* al!ohols by the !arbon to 'hi!h the hydro&yl group is atta!hed. Primary al!ohols are those in 'hi!h the hydro&yl group is atta!hed to the !arbon 'ith only one !arbon atta!hed. Se!ondary al!ohols are !ompounds in 'hi!h the #%, is atta!hed to a !arbon 'hi!h has t'o other !arbons atta!hed to it. "ertiary al!ohols are !ompounds in 'hi!h a hydro&yl group is atta!hed to a !arbon 'ith three atta!hed !arbons 596. Carbonyl group is a *amily o* *un!tional groups !omposed o* a !arbon atom double,bonded to an o&ygen atom: C;#. "he group is a !onstituent o* !arbo&yli! a!ids, esters, anhydrides, a!ylhalides, amides, and <uinones, and it is the !hara!teristi! *un!tional group o* aldehydes and 3etones 526. ldehydes are organi! !ompound !ontaining a terminal !arbony lgroup. "his *un!tional group, !alled analdehyde group, !onsists o* a !arbon atom bonded to a hydrogen atom 'ith a single !o)alent bond and an o&ygen atom 'ith a double bond. "hus the !hemi!al *ormula *or an aldehyde *un!tional group is ,C%;#, and the general *ormula *or analdehyde is 7,C%;#. Ketones *eatures a !arbonyl group-C;#/ bonded to t'o other !arbon atoms. "hey di**er *rom aldehydes in a 'ay that the !arbonyl is pla!ed bet'een t'o !arbons rather than at the end o* a !arbon s3eleton 596. "hey are also distin!t *rom other *un!tional groups, su!h as !arbo&yli! a!ids, esters and amides, 'hi!h ha)e a !arbonyl group bonded to a hetero atom. "he tests used in this e&periment are $u!as test, Chromi! !id test, 2,+, Dinitrophenylhydra(one, 0ehling1s test, "ollens1 Sil)er Mirror test and 2odo*orm test 5+6. $u!as test o*ten pro)ides !lassi*i!ation in*ormation *or al!ohols, as 'ell as a probe *or the e&isten!e o* the hydro&yl group. Substrates that easily gi)e rise to !ationi! !hara!ter at the !arbon bearing the hydro&yl group undergo this test readily= primary al!ohols do not gi)e a positi)e result. 5+6Chromi! a!id test dete!ts the presen!e o* a hydro&yl substituent that is on a !arbon bearing at least one hydrogen, and there*ore o&idi(able. 2,+,Dinitrophenylhydra(one test !an be used to <ualitati)ely dete!t the !arbonyl *un!tionality o* a 3etone or aldehyde *un!tional group. 0ehling1s "est and "ollens1 Sil)er Mirror "est are used to dete!t aldehydes. %o'e)er, 0ehling>s solution !an only be used to test *or aliphati! aldehydes , 'hereas "ollens> reagent !an be used to test *or both aliphati! and aromati! aldehydes. 2odo*orm "est is a test *or methyl!arbinol -se!ondary al!ohol 'ith ad?a!entmethyl group/ and methyl !arbonyl group.

EXPERIMENTAL A. Co!"o nd# U#ed

"he !ompounds used are n,butyl al!ohol, sec, butyl al!ohol, tert,butyl al!ohol, a!etaldehyde, n, butylaldehyde, ben(andehyde, a!etone, and isopropyl al!ohol.

B. Proced re $. So% &'%'() o* A%coho%# 'n +a(er

$o' mole!ular,'eight amines and o&ygen, !ontaining !ompounds li3e al!ohols, !arbo&yli! a!ids, aldehydes, and 3etones are the only soluble organi! !ompounds in 'ater. 2n *i)e di**erent test tubes named as to E, pla!e ten drops o* ethanol, n,butyl al!ohol, sec, butyl al!ohol, tert,butyl al!ohol and ben(yl al!ohol into the appropriate tube. dd 8 m$ o* 'ater to ea!h o* the test tubes and sha3e thoroughly. 2* a !loudiness results, !ontinue adding @.25 m$ o* 'ater at a time, 'ith )igorous sha3ing, until a homogenous dispersion results. 2* no !loudiness resulted a*ter adding 2.@ m$ o* 'ater, the al!ohol is soluble in 'ater.

"o prepare the reagent *or this test, add a solution o* 9 g o* 2,+,dinitrophenylhydra(ine in 85 m$ o* !on!. %2S#+ slo'ly, 'hile stirring to a mi&ture o* 2@ m$ o* 'ater and C@ m$ o* D5B ethanol. Stir and *ilter it. Pla!e a drop o* a li<uid sample into a small test tube. dd 5 drops o* D5B ethanol and sha3e it 'ell. dd 9 drops o* 2,+,dinitrophenylhydra(ine. 2* no yello' or orange,red pre!ipitate *orms, allo' the solution to stand *or at least 85 minutes.

2. Feh%'n34# Te#(
"his test 'as per*ormed on a!etaldehyde, n, butyraldehyde, a!etone, ben(aldehyde, and a!etophenone. 0ehling1s reagent 'as prepared by mi&ing e<ual amounts o* 0ehling1s and 0ehling1s E. 0ehling1s 'as prepared by dissol)ing C g o* hydrated !opper -22/ sul*ate in 8@@ m$ o* 'ater. 0ehling1s E 'as prepared by mi&ing 95 g o* Potassium sodium tartrate and 8@ g o* Sodium hydro&ide in 8@@,ml 'ater. 8,ml o* *reshly prepared 0ehling1s reagent 'as pla!ed into ea!h test tube. 9 drops o* the sample to be tested 'as added in to the tube. "he tubes 'ere then pla!ed in a bea3er o* boiling 'ater and !hanges 'ithin 8@,85 minutes 'ere obser)ed.

,. L ca# Te#(
"o prepare the reagent *or this test, dissol)e 8A g o* anhydrous (in! !hloride in 8@ m$ o* !on!. %C$. llo' the mi&ture to !ool. *ter !ooling, add 5@ mg o* the sample to 8 m$ o* reagent in a small )ial. Cap the )ial and sha3e )igorously *or a *e' se!onds. llo' the mi&ture to stand at room temperature. Per*orm the test on n-butyl al!ohol, sec,butyl al!ohol, tert-butyl al!oho, and ben(yl al!ohol. #bser)e the rate o* *ormation o* the !loudy suspension or the *ormation o* t'o layers.

5. To%%en#4 S'%6er M'rror Te#(

"his test 'as per*ormed on a!etaldehyde, ben(aldehyde, a!etone, n,butyraldehyde, and a!etophenone. "he reagent 'as prepared by adding 2 drops o* 5B Sodium hydro&ide solution to 2,ml o* 5B Sil)er nitrate solution and mi&ing thoroughly. .e&t, only enough 2B mmonium hydro&ide -!on!entrated ammonium hydro&ide is 2FB/ 'as added drop by drop and 'ithstirring to dissol)e the pre!ipitate. dding e&!ess ammonia 'ill !ause dis!repan!ies on the result o* the test. 0our test tubes 'ith 8,ml o* *reshly prepared "ollens1 reagent 'ere prepared. "'o drops ea!h o* the samples 'ere then added. "he mi&ture 'as sha3en and allo'ed to stand *or 8@ minutes. 2* no rea!tion has o!!urred, the test tube 'as pla!ed in a bea3er o* 'arm 'ater -95, 5@oC/ *or 5 minutes.

-. Chro!'c Ac'd Te#(

"his test 'as per*ormed on n-butyl al!ohol, sec-butyl al!ohol, tert,butyl al!ohol, n, butyraldehyde, ben(aldehyde, and a!etone. Dissol)e 8 drop o* li<uid or a small amount o* solid sample in 8 m$ o* a!etone in a small )ial. dd 2 drops o* 8@B a<ueous K2Cr2#C solution and 5 drops o* AM %2S#+.

.. ,/.0D'n'(ro"hen)%h)dra1one (e#(
"his test 'as per*ormed on a!etone, a!etaldehyde, n,butyraldehyde, ben(aldehyde, and a!etophenone.

7. Iodo*or! Te#(
"his test 'as per*ormed on a!etaldehyde, a!etone, a!etophenone, ben(aldehyde, and isopropyl al!ohol.

2 drops o* ea!h sample 'as pla!ed into its o'n small )ial or test tube. 2@ drops o* *resh !hlorine blea!h -5B Sodium hypo!hlorite/ 'as slo'ly added 'hile sha3ing to ea!h test tube and then, mi&ed. "he *ormation o* a yello' parti!ipate 'as noted.

Ta&%e -. Chro!'c ac'd (e#( re# %(#

Substan!e n-butyl al!ohol sec-butyl al!ohol tert-butyl al!ohol n, butyraldehyde ben(aldehyde a!etone Condensed Stru!tural 0ormula 7esults $ight yello' layer to light green layer Yello' layer to light green layer Yello' green layer #range layer #range to red layer $ight yello' layer to light green layer

RESULTS AND DISCUSSION

Ta&%e $. So% &'%'() o* A%coho% 'n +a(er
l!ohol Condensed Stru!tural 0ormula mount o* 'ater -in m$/ needed to produ!e homogenous dispersion 8 m$ 2 m$ 8.25 m$ Solubility in 'ater

Ethanol n-butyl al!ohol secbutyl al!ohol tertbutyl al!ohol Een(yl al!ohol

C%9C%2#% C%9C%2C%2#%

mis!ible mis!ible mis!ible

8 m$

mis!ible

A.5 m$

immis!ible

"able 9 sho's the rea!tion o* n, butyl al!ohol, se!,butyl al!ohol, tert,butyl al!ohol, n, butyraldehyde, ben(aldehyde, and a!etone to Chromi! !id test. .,butyl al!ohol, se!,butyl al!ohol, ben(aldehyde, and n,butyraldehyde green solution 'hereas tert,butyl al!ohol, and a!etone resulted to a yello' solution. Ta&%e .. ,/.0DNP re# %(#
Substan!e a!etaldehyde n, butyraldehyde Een(aldehyde a!etone Condensed Stru!tural 0ormula 7esults #range ppt. #range ppt. #range ppt. #range ppt.

"able 8 sho's that ethanol, n,butyl al!ohol, sec,butyl al!ohol, and tert,butyl al!ohol are all mis!ible 'ith 'ater 'ith the e&!eption o* ben(yl al!ohol 'hi!h e&hibited insolubility. Ta&%e ,. L ca# (e#( re# %(# Condensed 7esults
Stru!tural 0ormula C%9C%2C%2#%

Substan !e n-butyl al!ohol secbutyl al!ohol tertbutyl al!ohol Een(yl al!ohol

2n*eren!e mis!ible mis!ible immis!ible mis!ible

no rea!tion no rea!tion Cloudy *ormation no rea!tion

"able + sho's the rea!tion o* a!etaldehyde, n, butyraldehyde, ben(aldehyde, and a!etone to 2,+,D.P test. ll the samples e&hibited positi)e result be!ause they all *ormed an orange pre!ipitate. %en!e, 2,+,D.P test pro)ed that the samples are !arbonyl,!ontaining !ompounds and are either aldehydes or 3etones. Ta&%e 2. Feh%'n34# (e#( re# %(#
Substan!e a!etaldehyde Condensed Stru!tural 0ormula 7esults Eri!3 red ppt. 2 layer: green, bro'n Eri!3 red ppt. 9 layers: Colorless, light

"able 2 sho's the rea!tion o* butanol deri)ati)es to $u!as "est. .,butyl al!ohol, se!, butyl al!ohol, and ben(yl al!ohol yielded a !lear solution 'hen sub?e!ted to $u!as "est 'hereas tert,butyl al!ohol resulted to a !loudy immis!ible suspension 'hi!h e)entually *ormed t'o layers.

n, butyraldehyde

Een(aldehyde a!etone

blue, royal blue Elue solution 'ith orange ppt. .o !hange

2t is sho'n in "able 5 that a!etaldehyde, n, butyraldehyde, and ben(aldehyde e&hibited positi)e result. !etaldehyde, in parti!ular turned *rom blue to muddy green then *ormed a !rude red pre!ipitate upon heating. "hese three sample !ompounds 'hi!h e&hibited positi)e result to 0ehling1s test are all aldehydes. Ta&%e 5. To%%en#4 S'%6er M'rror (e#( re# %(#
Substan!e a!etaldehyde n, butyraldehyde Een(aldehyde a!etone Condensed Stru!tural 0ormula 7esults Sil)er mirror= bla!3 ppt. gray solution Clear solution Gray solution

596 %ydro&yl Group. -2@8@/. 2n En!y!lopKdia Eritanni!a. 7etrie)ed September 8D, 2@8@, *rom En!y!lopKdia Eritanni!a #nline: http:JJ'''.da)iddarling.in*oJen!y!lopedia JPJphenol.html. 5+6 Shriner, 0uson, Curtin. -8DA+/. Systemati! 2denti*i!ation o* #rgani! Compound: $aboratory Manual 0i*th Edition. Lohn Miley I Sons, 2n!. .e' Yor3: Gan %o**mann Press

2n table A, a!etaldehyde prdou!ed a sil)er mirror 'ith a bla!3 ppt 'hen sub?e!ted to "ollens1 test 'hile the other !ompounds did not *ormed any sil)er mirror. "he *ormation o* the sil)er mirror may be a**e!ted by the preparation o* the "ollens1 reagent. Ta&%e 7. Iodo*or! (e#( re# %(#
Substan!e a!etaldehyde n, butyraldehyde Een(aldehyde 2sopropyl al!ohol Condensed Stru!tural 0ormula 7esults Ero'n ppt. 7edish bri'n ppt. Yello' ppt. 7ed solution

"able C sho's that among the sample !ompounds tested, a!etaldehyde, a!etone, a!etophenone, and isopropyl al!ohol e&hibited positi)e

REFERENCES
586 Eayguen, .G., Cru(, C."., de Guia, 7.M, $ampa, 0.0., PeHa, G."., Sarile, .S. and "orres, P.C. -2@@D/,$aboratory Manual in #rgani! Chemistry,CIE Publishing, 2n!. 526 Carbonyl http:JJen.'i3ipedia.orgJ'i3iJCarbonyl