COMPARATIVE INVESTIGATION OF ORGANIC COMPOUNDS Harvie M. Barcellano, Dariene Joie B. Bautista, Florianne May D. Beltran, Jerika Prem M. Benjamin, Rochelle Anne C. Burata and Emmanuel R. Caliwa !rou" # #! Medical $echnoloy %ranic Chemistry &a'oratory ABSTRACT $he o'jecti(e o) the e*"eriment is to di))erentiate oranic com"ounds in terms o) certain intrinsic "hysical "ro"erties, 'eha(ior towards inition test, and in)rared s"ectra o) their )unctional rou"s. Physical "ro"erties are determined 'y o'ser(in the sam"les+ "hysical state at room tem"erature, color and odor. odor. olu'ility and misci'ility were tested usin the )ollowin )ollowin reaentsreaents- water, water, / 0a%1 solution, solution, and / 1Cl solution. solution. %nly dichlorom dichloromethan ethane e a""eare a""eared d to 'e immisci'le in the three sol(ents, the rest 'ein slihtly misci'le or misci'le. Acidity and 'asicity o) the com"ounds were determined 'y the use o) litmus "a"er. %nly "henol and 'en2oic acid was o'ser(ed to 'e acidic, while ethylamine as the sole 'asic com"ound, the rest 'ein neutral. 3nition test was also conducted, takin note o) the )lame "roduced i) )lamma'le. Amon the sam"les, only dichloromethane, "henol, and 'en2oic acid were identi)ied to 'e non4)lamma'le. 3n)rared 3n)rared s"ectrosco s"ectrosco"y "y,, which which is use)ul use)ul )or determinin determinin the )unctional )unctional rou"s "resent "resent in an oranic com"ound, was used to )ind the 3R "eaks o) each sam"le. From the e*"eriment, it could 'e concluded
that oranic com"ounds ha(e di))erent "ro"erties and that the ty"es o) 'ond and )unctional rou"s o) these oranic com"ounds a))ect those "ro"erties. INTRODUCTION !enerally, oranic com"ounds can 'e classi)ied into nto hydrocar hydrocarbons bons and hydrocarbon derivatives, 'ase 'ased d on the the re"l re"lac acem emen entt o) hydro ydroe en n 'y anot anothe herr elem elemen entt or 'y a rou rou" " o) di)) di))er eren entt elements. elements. "eci)ica "eci)ically lly,, oranic oranic com"ounds com"ounds are con(en con(enien iently tly classi classi)ie )ied d as di))er di))erent ent classe classes s o) hydrocar'on deri(ati(es 'ased on the su'stituent elem elemen entt or rou rou" " o) hih hihes estt "rio "riori rity ty to the the hydro hydroca car'o r'on. n. Funct Function ional al rou"s rou"s "rese "resent nt in an ora orani nic c com" com"ou ound nd can can 'e dete determ rmin ined ed usin usin 567 in)rared s"ectrosco"y . %ra %rani nic c com" com"ou ound nds s are are the the com" com"le le* * com"ounds o) car'on. Because car'on atoms 'ond 'ond to one another easily, the 'asis o) most oranic com"ounds is com"rised o) car'on chains that (ary in lenth and sha"e. 1ydroen, nitr nitro oen en,, and and o*y o*yen en atom atoms s are the the most most common atoms that are enerally attached to the car'on atoms. Each car'on atom has 8 as its (alence num'er which increases the com"le*ity o) the com"ounds that are )ormed. ince car'on atoms are a'le to create dou'le and tri"le 'onds with with othe otherr atom atoms, s, it )urt )urthe herr also also rais raises es the the likelihood )or (ariation in the molecular make4u" o) oranic com"ounds. 1ydrocar'ons are the sim"lest class o) oranic com"ounds and are com"osed solely o) hydroen and car'on. $his class can 'e )urther di(ided into two rou"s- ali"hatic hydrocar'ons ali"hatic hydrocar'ons and aromatic hydro hydroca car'o r'ons ns.. Ali"ha Ali"hatic tic hydroc hydrocar' ar'ons ons can 'e classi)ied 'ased on the structure and 'ondin o) the car'on skeleton into three rou"s- alkanes, alkenes, and alkynes. Aromatic hydrocar'ons or aren arenes es,, whic which h cont contai ain n a 'en2 'en2en ene e rin rin,, were were oriinally named )or their "leasant odors. $hese com"ounds "ossess s"ecial "ro"erties due to the
delocali2ed electron density electron density in 'en2ene, includin addi additi tion onal al sta' sta'il ili2 i2at atio ion n due due to the the syst system em o) conjuated rins consistin o) unsaturated 'onds, lone "airs, and em"ty or'itals597. %ranic com"ounds "ossess di))erent "hysical "ro"erties, which are intrinsic 567. $hey may (ary in thei theirr "hys "hysic ical al stat state e at room room tem" tem"er erat atur ure, e, which which can can indica indicate te the stren strenth th o) intera interacti cti(e (e )orces )orces that that e*ist e*ist 'etwee 'etween n its molecu molecules les,, color color,, odor odor and and solu solu'i 'ili lity ty indi indi)) ))er eren entt rea reaen ents ts.. $he $he e*" e*"erim erimen entt aims ims to di)) di))er eren enti tiat ate e ora oran nic com"ounds in terms o)- certain intrinsic "hysical "ro"erties, es, 'eha(ior tow towards ini initi tion on,, and in)ra in)rared red s"ectr s"ectra a o) their their )unctional rou"s. Cond ensed structural )ormula o) the com"ounds used5#76. Cyclohe*ane
#.DCM C1#Cl#
9. Ethanol C19C1#%1
Dro"s o) the the sam"le sam"le tested tested its a
8. Phenol
. Ben2oic Acid
. I/ni&ion Te%& 94 dro"s dro"s o) o) the the li
RESUTS AND DISCUSSION
:. Ethyl Acetate
;. Ethylamine C19C1#01#
EXPERIMENTA A. Co!"o#n$% Te%&e$ Cyclohe*ane, Dichloromethane, Ethanol, Phenol, Ben2oic acid, Ethyl acetate, and Ethylamine B. Proce$#re '. P()%ical S&a&e, Color an$ O$or $he "hysical state o) the the sam"le sam"le was was o'ser(ed in room tem"erature. Color and odor was noted. *.Sol#+ili&) Pro"er&ie% $he sam"les sam"les were were introd introduced uced into clean clean and and dry test tu'es. Four dro"s o) each sam"le were introduced i) the sam"le is a li.6 o) the sam"le was introduced i) the sam"le is solid. $he solid sam"les were rinded to increase the sur)ace area. $he sol(ent was added dro" wise, countin the num'er o) dro"s o) sol(ent added to a total o) 9 m&. Any color chanes, warmin or e))er(escence, solu'le?insolu'le, misci'le?immisci'le were noted. . Reac&ion -i&( i&!#% Pa"er
All o) the hydrocar'ons hydrocar'ons tested were colorless, e*ce e*ce"t "t "hen "henol ol,, whic which h is oran orane e in colo colorr, and and 'en2oic acid which is white in color. $he odors o) the com"ounds were
to com" com"le lete te com' com'us usti tion on whic which h caus causes es the the )ormat )ormation ion o) an un'urn un'urned ed car'on car'on.. 3n terms terms o) deree o) luminosityaromatic com"oundunsaturated com"oundunsaturated hydrocar'on hydrocar'on saturated hydrocar'on. Com"lete Com"lete com'ustio com'ustion n is indicated indicated 'y a 'lue )lame )lame non non lumino luminous us and there there is more more heat heat than liht, the car'on is com"letely o*idi2ed. # C6>1## 96 %#
→
#> C%# # 1#%
3ncom"lete com'ustion is indicated 'y a yellow )lame )lame lumin luminous ous and and there there is much much liht liht than than heat, the car'on is not com"letely o*idi2ed. 567 3n)rared s"ectrosco"y is "articularly use)ul )or determinin the ty"es o) 'onds that are "resent in a molecule. $he "rimary use o) 3R is to identi)y the )unctional rou"s "resent in a molecule. From the e*"eriment, it could could 'e concluded concluded that oranic com"ounds ha(e di))erent "ro"erties and that the ty"es o) 'ond and )unctional rou"s o) these oranic com"ounds a))ect those "ro"erties.
REFERENCES4 567 Bathan Bathan,, !.3., !.3., Bay68 #>68.. Laboratory Manual in Organic Chemistry. ManilaCHE Pu'lishin, 3nc. P.:I 5#7 Formulas o) 3noranic and %ranic Com"ounds. n.d.. 3n ChemWiki . Retr Retrie ie(e (ed d 0o(em'er #> #>6 )rom htt"-??chemwiki.ucda(is.edu?Ph htt"-??chemwiki.ucda(is.edu?PhysicalChemistry ysicalChemistry?? KuantumMechanics?>I.$he1yd KuantumMechanics?>I.$he1ydroenAtom?A roenAtom?A tomic$heory?ChemicalCom"ounds? tomic$heory?ChemicalCom"ounds?Formulas Formulaso) o) 3noranicand%ranicCom"ounds 3noranicand%ranicCom"ounds 597 @hat @hat are are %rani %ranic c Com"ou Com"ounds ndsL. L. n.d. n.d... 3n Retrie(e e(ed d 0o 0o(e (em'e m'err #>, #>6 #>6 )rom )rom wise wiseGe Geek ek.. Retri htt"-??www.wiseeek.com?what4are4oranic4 com"ounds.htm
Ta+le '. Com"arati(e 3n(estiation o) %ranic Com"ounds Te%& Co!"o#n
%$C)clo(e5ane
DCM
E&(anol
P(enol
Ben6oic aci$
E&
P()%ical S&a&e a& RT
&i
&i
&i
&i
olid
&i<
A""earance
Clear
Clear
Clear
Clear
Crystalline
Cl
Color
Colorless
Colorless
Colorless
%rane
@hite
Co
O$or
Dies Diesel el4l 4lik ike e odor odor
erose rosene ne4l 4lik ike e odor
alc alcoho ohol4li l4lik ke odor
Burnt urnt "last lastic ic44lik like odor
%dorless
Pl od
Sol#+ili&) in H* O
Misci'le
3mmisci'le
Misci'le
lihtly misci'le
lihtly solu'le
lihtly misci'le
3mmisci'le
Misci'le
Misci'le- orane to (iolet
olu'le
li mi 'u Mi
lihtly misci'le
3mmisci'le
Misci'le
Misci'le- orane to white
lihtly so solu'le
Mi
Reac&ion -i&( li&!#% "a"er
Blue to Blue Red to Red
Blue to Blue Red to Red
Blue to Blue Red to Red
Blue to Red Red to Red
Blue to Red Red to Red
Bl Re
I/ni&ion &e%&
Flamma'leyellow4orane
0on4) on4)llamma amma'l 'le e
Flam Flamma ma' 'le- 'lue lue and orane
0on4)lamma'le
0on4)lamma'le
Fla or
8'9
C;C %&re&c(4 6#>>4N>>, (ery @ C;H +en$4 689469>, 4M C;H %&re&c(4 9>>>4#N8>,
C;Cl4 N>4;N>, C;C %&re&c(4 6#>>4N>>, (ery @ C;H %&re&c(4 9>>>4#N8>,
O;H %&re&c(4 9;>>496>>, (ery O;H +en$4 68#>4 698>, M4@ C;O %&re&c(4 6#9>46>>>, 4M C;C %&re&c(4 6#>>4N>>, (ery @ C;H %&re&c(4 9>>>4#N8>, C;H +en$4 68;4 69>, 4M
O;H %&re&c(4 9;>>496>>, (ery O;H +en$4 68#>4 698>, M4@ C;O %&re&c(4 6#9>46>>>, 4M C=C ar. %&re&c(4 6:#>468N>, M4@ C;C %&re&c(4 I>>4 :>>, 4M C;H %&re&c(4 96>>49>>>, M4@
C=C ar. %&re&c(4 6:#>4 68N>, M4@ C;H %&re&c(4 96>>49>>>, M4 @ O;H %&re&c(4 99>>4#>>, 'road O;H +en$4 688>469I>, M C=O %&re&c(4 6;9>46:N>, C;O %&re&c(4 69#>46#6>,
C 6; C; 6# C; 9> C; 68 M C; 6# (e
07 NaOH %oln. 07 HCl %oln.
O+%erve$ "rinci"al IR "ea:% 2c!;'3<
O stron, stron, M medium, @ weak weak