CLASSIFICATION TESTS FOR HYDROCARBONS (CYCLOHEXANE, CYCLOHEXENE, BENZENE, TOLUENE)

Dianne I. Pascua, Francesca F. Perez, Romulo S. Perez, Lia S. Priela and Zeth D.R. Raquedan Group 8 2C edical !eechnolo"# $r"anic Chemistr# La%orator#

ABSTRACT
In this e&periment, the h#drocar%ons c#clohe&ane, c#clohe&ene, %enzene and toluene 'ere used as samples. !he or"anic compounds stated 'ere classi(ied accordin" to di((erent ph#sical and chemical properties. !he samples 'ere (irst tested accordin" to their solu%ilit# in ) 2S$*. Second 'as (lamma%ilit# test, + drops o( sample 'ere placed in an e,aporatin" dish and then lit 'ith a match. !hird is the test (or acti,e unsaturation, the samples 'ere tested usin" -ae#er.s !est and -romine !est. /ourth is (or aromaticit#, it 'as determined %# su%0ectin" the compounds to 1itration. Lastl#, the %asic o&idation test, 8 drops o( 22 3 n$ * solution and + drops o( 452 1a$) 'ere added to * drops o( each o( the sample. 6ll compounds sho'ed immisci%ilit# in concentrated ) 2S$* and also all o( them i"nited durin" the (lamma%ilit# test. 6ll 'ere o%ser,ed as not acti,el# unsaturated e&cept (or the c#clohe&ane. !he samples turned out to %e aromatic compounds e&cept (or c#clohe&ane and c#clohe&ene. 6ll compounds are not o&idized e&cept (or c#clohe&ene.

INTRODUCTION
)#drocar%ons are the simplest or"anic compounds. Containin" onl# car%on and h#dro"en, the# can %e strai"ht7chain, %ranched chain, or c#clic molecules. Car%on tends to (orm (our %onds in a tetrahedral "eometr#. )#drocar%ons ma# %e di,ided into t'o lar"e classes namel#8 Saturated h#drocar%ons and unsaturated h#drocar%ons. Saturated h#drocar%ons are the simplest t#pe o( or"anic compounds. !he# are h#drocar%ons in 'hich all car%on7car%on %onds are sin"le %onds. 6n e&ample o( a saturated h#drocar%on is an al9ane. :nsaturated h#drocar%ons are h#drocar%ons that contain one or more car%on7car%on multiple %onds li9e dou%le %onds, triple %onds, or %oth. Saturated and :nsaturated h#drocar%ons ha,e similar ph#sical properties, %ut their chemical properties are di((erent. :nsaturated h#drocar%ons are chemicall# more reacti,e than saturated ones. !his is %ecause o( the presence o( car%on7car%on multiple %onds in such compounds and these multiple %onds ser,e as locations 'ere chemical reactions can occur. ;4<

F !"re ). Unsa$"ra$e% H&%r'car('n C#clohe&ane is a c#cloal9ane 'ith the molecular (ormula C=)42. C#clohe&ane is used as a nonpolar sol,ent (or the chemical industr#, and also as a ra' material (or the industrial production o( adipic acid and caprolactam, %oth o( 'hich %ein" intermediates used in the production o( n#lon. $n an industrial scale, c#clohe&ane is produced %# reactin" %enzene 'ith h#dro"en. Producers o( c#clohe&ane account (or appro&imatel# 44.*2 o( "lo%al demand (or %enzene. -ecause o( its unique chemical and con(ormational properties, c#clohe&ane is also used in la%s in anal#sis and as a standard. C#clohe&ane has a distincti,e deter"ent7li9e odor, reminiscent o( cleanin" product >in 'hich it is sometimes used?. ;2<

F !"re *. C&c+',e-ane F !"re #. Sa$"ra$e% H&%r'car('n

C#clohe&ene is a h#drocar%on 'ith the (ormula C=)45. !his c#cloal9ene is a colorless liquid 'ith a sharp smell. It is an intermediate in ,arious industrial processes. C#clohe&ene is not ,er# sta%le upon lon" term stora"e 'ith e&posure to li"ht and air %ecause it (orms pero&ides. ;+<

and it is 'idel# used as an industrial (eedstoc9 and sol,ent. ;*<

F !"re /. T'+"ene F !"re *. C&c+',e-ene -enzene is a colorless, (lamma%le liquid 'ith a s'eet odor. It e,aporates quic9l# 'hen e&posed to air. -enzene is (ormed (rom natural processes, such as ,olcanoes and (orest (ires, %ut most e&posure to %enzene results (rom human acti,ities. -enzene is amon" the 25 most 'idel# used chemicals in the :nited States. It is used mainl# as a sol,ent >a su%stance that can dissol,e or e&tract other su%stances? and as a startin" material in ma9in" other chemicals. In the past it 'as also commonl# used as a "asoline additi,e, %ut this use has %een "reatl# reduced in recent decades. -enzene is also a natural part o( crude oil, "asoline, and ci"arette smo9e. ;*< isci%ilit# is the propert# o( liquids to mi& in all proportions, (ormin" a homo"eneous solution. In principle, the term applies also to other phases >solids and "ases?, %ut the main (ocus is usuall# on the solu%ilit# o( one liquid in another. Dater and ethanol, (or e&ample, are misci%le %ecause the# mi& in all proportions. -# contrast, su%stances are said to %e immisci%le i( a si"ni(icant proportion does not (orm a solution. $ther'ise, the su%stances are considered misci%le. /or e&ample, %utanone is si"ni(icantl# solu%le in 'ater, %ut these t'o sol,ents are not misci%le %ecause the# are not solu%le in all proportions. ;E< /lamma%ilit# is ho' easil# somethin" 'ill %urn or i"nite, causin" (ire or com%ustion. !he de"ree o( di((icult# required to cause the com%ustion o( a su%stance is quanti(ied throu"h (ire testin". Internationall#, a ,ariet# o( test protocols e&ist to quanti(# (lamma%ilit#. !he ratin"s achie,ed are used in %uildin" codes, insurance requirements, (ire codes and other re"ulations "o,ernin" the use o( %uildin" materials as 'ell as the stora"e and handlin" o( hi"hl# (lamma%le su%stances inside and outside o( structures and in sur(ace and air transportation. ;=< !he -ae#er test uses dilute potassium perman"anate to o&idize the car%on7car%on dou%le or triple %ond. ItFs called o&idation %ecause the dou%le %ond is replaced %# a h#dro&# "roup >an $) "roup?. !he car%onFs char"e "oes (rom %ein" G4 to G2, so it loses an electron and is thus o&idized. ;@<

F !"re .. Benzene !oluene is an aromatic h#drocar%on 'ith a molecular (ormula o( C@)8, molar mass o( A2.4* "Bmol, and a %oilin" point o( 445.=CC. !oluene reacts as a normal aromatic h#drocar%on to'ards electrophilic aromatic su%stitution. It is a 'ater7 insolu%le liquid 'ith a smell o( paint thinners,

6romaticit# is a propert# associated 'ith the e&tra sta%ilit# o( certain t#pes o( p s#stems. /undamentall# it arises (rom ha,in" the ma&imum num%er o( electrons in the p %ondin" molecular or%itals. 6s 'e 'ill see, it is not restricted to %enzene, su%stituted %enzenes, =7 mem%ered rin"s or 0ust h#drocar%ons. !he propert# o( aromaticit# is "enerall# a%out a si"ni(icant e&tra sta%ilit# associated 'ith a resonance delocalized structure. !his e&tra sta%ilit# moderates the reacti,it# o( these s#stems compared to al9enes and means aromatics can %e considered as their o'n (unctional "roup. ;8< !he o%0ecti,es o( the stud# are8 >4? !o di((erentiate h#drocar%ons in terms o(8 >a? intrinsic ph#sical properties and >%? chemical properties in terms o( structure and %eha,ior. >2? !o anal#ze a h#drocar%on and determine i( it is saturated acti,el# unsaturated, aromatic or an arene. ;A<

EXPERI0ENTAL A. C'12'"n%s $es$e% ('r sa12+es "se%)

C#clohe&ane, C#clohe&ene, -enzene, !oluene, conc. )2S$*, 22 3 n$* soln, 5.E2 -r2 in CCl*, conc. )1$+, 452 1a$) soln, distilled )2$

B. Pr'ce%"re
6. Ph#sical State, $dor, and Color !he ph#sical states o( the sample compounds he&ane, heptane, c#clohe&ane, c#clohe&ene, and %enzene 'ere o%ser,ed at room temperature. !he color and odor 'as noted. -. Solu%ilit# in )2S$* !o each o( the sample, 45 drops o( conc. )2S$* 'as put. 6n# color chan"e or 'armin" e((ects 'ere noted. C. I"nition !est In an e,aporatin" dish, +7E drops o( samples 'ere placed and 'as li"hted usin" a match. 6n# (lames nd soot produced are noted. D. 6cti,e Saturation 4. -ae#er.s !est 2 drops o( 22 3 n$* 'ere added to E drops o( the sample in a dr# test tu%e. !he test tu%e 'as sha9en ,i"orousl# and the rate and e&tent at 'hich the rea"ent is decolorized 'as o%ser,ed .!he (ormation o( a %ro'n suspension 'as noted.

It 'as compared 'ith 'ater as a ne"ati,e control. !he decolorization o( the rea"ent 'as considered immediate i( it occurred 'ithin a minute. !he results 'ere noted do'n. 2. -romine !est !o E drops o( sample in a test tu%e, 45 drops o( 5.E2 -r2in CCl* rea"ent 'ere added. !he test tu%e 'as sha9en ,i"orousl# and the rate and e&tent o( decolorization 'as o%ser,ed. It 'as compared 'ith 'ater as a ne"ati,e control. I( the rea"ent (ailed to decolorize 'ithin a minute, the reaction mi&ture 'as e&posed to sunli"ht. H. 6romaticit# >1itration? 2 ml concentrated )1$+ 'as placed in an Hrlenme#er (las9. !he (las9 'as immersed in an e,aporatin" dish containin" 'ater and 2 ml o( concentrated )2S$* 'as added "raduall#. !he resultin" mi&ture >nitratin" mi&ture? 'as cooled in room temperature. 8 drops o( the nitratin" mi&ture 'ere added to E drops o( the sample in a dr# test tu%e. !he test tu%e 'as sha9en to ensure complete mi&in". !he (ormation o( a #ello' oil# la#er or droplet 'as noted, and then it 'as diluted 'ith 25 drops o( 'ater. I( there 'as no apparent reaction o%ser,ed 'ithin a minute, the test tu%e 'as placed in a 'ater %ath >E5CC? (or 45 minutes. It 'as diluted 'ith 25 drops o( 'ater and the results 'ere noted do'n. /. -asic $&idation 8 drops o( 22 3 n$* solution and + drops o( 452 1a$) solution 'ere added to * drops o( the sample in a test tu%e. Hach test tu%e 'as su%0ected to a 'ater %ath (or 2 minutes. 6n# color chan"e and (ormation o( %ro'n precipitate 'as o%ser,ed and noted do'n.

RESULTS AND DISCUSSION

Compounds !ested C#clohe&ene -enzene

C#clohe&ane Condensed structural (ormula

!oluene

6. Ph#sical State at R! Color $dor -. Solu%ilit# in Concentrated )2S$* In(erence C. i"nition !est In(erence D. -ae#er.s !est -romine test In(erence H. !est (or aromaticit#8 nitration In(erence /. -asic $&idation

Liquid colorless Ru"%#7li9e 1o color chan"e immisci%le $ran"e (lame (lamma%le 1o decolorization Did not decolorize misci%le 1o color chan"e immisci%le 1o ppt

Liquid colorless Ru"%#7li9e -ro'n isci%le $ran"e (lame /lamma%le Decolorized Decolorized isci%le -ro'n soln isci%le 1o ppt

Liquid Colorless Ru"%#7li9e #ello' misci%le $ran"e (lame (lamma%le 1o decolorization 1o decolorization misci%le Iello' oil# la#er immisci%le 1o ppt

Liquid colorless Ru"%#7li9e #ello' isci%le $ran"e (lame /lamma%le 1o decolorization Decolorized isci%le Iello' oil# la#er immisci%le -lac9 ppt

Ta(+e #. Res"+$s 3'r $,e C+ass 3 ca$ 'n '3 H&%r'car('ns

!hese are the results (rom the procedures done (or the classi(ication o( )#drocar%ons accordin" to misci%ilit#, (lamma%ilit#, acti,e unsaturation, aromaticit# >or nitration? and o&idation.

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CONCLUSION
-ased on the results, it 'as concluded that c#clohe&ane is non7aromatic and not acti,el# unsaturated. C#clohe&ene is non7aromatic and acti,el# unsaturated. -oth %enzene and toluene are aromatic and not acti,el# unsaturated.

REFERENCES
;4< 1a,e, R. )#per Ph#sics J Chemistr#. http8BBh#perph#sics.ph#7 astr."su.eduBh%aseBor"anicBh#drocar%on.html AB45B4+

studentBolcB"raphicsBcare#5*ocBre(Bch44aromatic it#.html AB45B4+ ;A< -a#quen, 6., Cruz, C., de Guia, R., Lampa, /., Pena, G., Sarile, 6. and !orres, P. >255A?. La%orator# anual in $r"anic Chemistr#. anila8 C L H Pu%lishin", Inc. p. 8478*