CHM143L Organic Chemistry 2 Laboratory

3rd Quarter SY 2013-2014 rou! "o# $% &he '(coho(ics

Preliminary Tests and Solubility Classification of Organic Compounds
Martin, Marilen
1
, Taeda, John Paul, D, C!M1"#$%&#1
'
1
)ro*essor+ Schoo( o* Chemica( ,ngineering+ Chemistry and -iotechno(ogy+ Ma!ua .nstitute o* &echno(ogy/
2
Student 0s1+ Sub2ect3Section+ Schoo( o* Chemica( ,ngineering+ Chemistry and
-iotechno(ogy+ Ma!ua .nstitute o* &echno(ogy
ABSTRACT
This experiment was about using the two major qualitative schemes, namely preliminary tests and solubility classiication, in
identiying an organic compound! "n the preliminary tests, the physical state, odor, color, and ignition test were noted! The
second test used was the solubility classiication, wherein the solvents used were water, ether, #Cl, $a%#, $a#C%&, and
#'S%( along with litmus paper and phenolphthalein in classiying each compound based on their solubility and color change!
A scheme was ollowed until it arrived at a certain solubility class such as ), Sn, S, $, Sa, Sb, B, A*, and A'! This was perormed
with aid o the reagents necessary, apparatuses or preliminary tests such as Bunsen burner, nichrome wire, and porcelain
crucible with cover, and micro test tubes or the solubility tests! Ater these were perormed to +nown compounds, the group
applied both o these tests to the un+nown samples and the determined solubility classes was aided by the data obtained
rom the preliminary tests! ,nortunately towards the end o the experiment, errors were ound on the data regarding the
solubility classes o some o the +nown compounds and one o the un+nown compounds! The two un+nown compounds
were identiied to have an ) solubility class- one is a halide and the other one is an n.aliphatic halide! /or the group, there
were no problems regarding the preliminary test! The only problem was regarding the solubility tests, because observation
errors can be easily encountered here! But despite such errors mentioned earlier, the group was able to achieved the
objectives given by the experiment!
"$TR%0,CT"%$
&he ana(ysis and identi*ication o* un4no5n organic
com!ounds constitutes a 6ery im!ortant as!ect in terms o*
e7!erimenta( organic chemistry# ' systematic a!!roach has been
gi6en regarding the c(assi*ication o* organic com!ounds# 8rom
the genera( scheme o* ana(ysis+ t5o ma2or !arts are the
!re(iminary tests and the so(ubi(ity c(assi*ication test#
)re(iminary tests note the !hysica( characteristics o* a
!articu(ar organic com!ound% !hysica( state+ co(or+ odor+ and
ignition3*(ame test# .t is im!ortant to note the !hysica( state o* the
com!ound because it can a(so re(ate to its so(ubi(ity and 6o(ati(ity+
and that de!ending on it+ 5here on(y certain !uri*ication
techni9ues can be used# Co(or can a(so be used in identi*ying an
un4no5n organic com!ound# .t can be due to im!urities or
chromo!horic *unctiona( grou!s+ 5herein they !roduce co(or by
se(ecti6e (ight absor!tion# Odor is a(so one im!ortant as!ect in
determining an un4no5n sam!(e# Some notab(e odors are *rom
amines that ha6e *ish-(i4e odor+ esters that ha6e a !(easant *ruity
sme((+ and acids that ha6e a shar!+ biting odor# ,7tra caution
must be done here because some com!ounds !ossess corrosi6e
6a!ors# Last(y+ ignition test is a(so im!ortant *or identi*ication+
5hether a meta( is !resent in a com!ound+ or that it contains
either an a(i!hatic or aromatic hydrocarbon de!ending on the
co(or o* the *(ame !roduced#
&he second ma2or scheme is ca((ed the so(ubi(ity
c(assi*ication# So(6ents such as 5ater+ ether+ :; sodium
hydro7ide+ :; sodium bicarbonate+ :; hydroch(oric acid+ and
concentrated su(*uric acid so(utions are uti(i<ed in order to
obser6e the so(ubi(ity !ro!erties o* an un4no5n organic
com!ound# &he manner in 5hich the com!ound is so(ub(e to
certain so(6ents mentioned ear(ier can be c(assi*ied in terms o*
the so(ubi(ity c(ass# 8rom the so(ubi(ity c(ass+ !ossib(e
com!ounds can be deduced *rom the un4no5n com!ound# &hey
can be c(assi*ied as S+ Sn+ Sa+ Sb+ -+ '1+ '2+ "+ and =# .* it *a((s
under S+ it can be sa(ts o* organic acids+ amino acids+
carbohydrates+ or !o(y*unctiona( com!ounds 5ith hydro!hi(ic
*unctiona( grou!s# .* it *a((s under Sn+ it can be mono*unctiona(
a(coho(s+ a(dehydes+ 4etones+ amides+ esters+ amines+ and many
more 5ith *i6e carbons or *e5er# .* it *a((s under Sa+ it can be
mono*unctiona( carbo7y(ic acid 5ith *i6e carbons o* *e5er or
ary(su(*onic acids# .* it *a((s under Sb+ it can be mono*unctiona(
a(i!hatic an aromatic amines 5ith si7 carbons or *e5er# .* it *a((s
under -+ it can be a(i!hatic amines+ ani(ines+ or some ethers# .* it
*a((s under '1+ it can be strong organic acids# .* it *a((s under '2+ it
can be 5ea4 organic acids# .* "+ a(coho(s+ a(dehydes+ 4etones+ or
esters 5ith one *unctiona( grou! and more than *i6e but *e5er
than nine carbons+ and i* =+ saturated hydrocarbons+
ha(oa(4anes+ and other deacti6ated aromatic com!ounds#
Experiment 01 Group No. 8 January 21. 2014 1 of 4
CHM143L Organic Chemistry 2 Laboratory
3rd Quarter SY 2013-2014 rou! "o# $% &he '(coho(ics
&his e7!eriment e7amines 6arious com!ounds using
di**erent !re(iminary tests+ identi*ies the so(ubi(ity c(ass+ and uses
these scheme in identi*ying an un4no5n com!ound#
1AT2R"A3S A$0 12T#%0S
&his e7!eriment consisted o* t5o !arts% )re(iminary
&ests and So(ubi(ity C(assi*ication &ests# &he a!!aratuses used
5ere dro!!ers+ micro test tubes+ test tube rac4+ !orce(ain
crucib(es 5ith co6er+ nichrome 5ire+ -unsen burner+ and hot
!(ate# &he reagents used 5ere co!!er nitrate+ acetic acid+ buty(
bromide+ ethano(+ sucrose+ butera(dehyde+ ethanoic acid+
methy(amine+ nitro!heno(+ diethy( ether+ ben<oic acid+ !ro!anone+
:; HC(+ 1:; HC(+ :; "aOH+ :; "aHCO3+ and conc# H2SO4#
8or the )re(iminary &ests !art+ the test com!ounds 5ere
co!!er nitrate+ acetic acid+ and t5o un4no5ns# &hey 5ere
obser6ed in terms o* their !ro!erties such as !hysica( state+
co(or+ odor+ and ignition test 0!resence o* meta(1# 8or the ignition
test !art+ a sma(( amount such as 0#10 g *or so(id and 0#:0 m( *or
(i9uid o* the substance to be tested in a !orce(ain crucib(e# "e7t+
it 5as heated s(o5(y unti( ignition 5as com!(ete and the *o((o5ing
5ere obser6ed% *(ammabi(ity and nature o* the *(ame+ i* any
6a!our or gas e6o(6ed and its odor+ i* any residue 5as (e*t a*ter
ignition+ and i* so(id+ note 5hether it me(ted and the manner by
5hich it me(ted# 8or substances that ha6e residues (e*t+ a *e5
dro!s o* disti((ed 5ater 5as added and the so(ution 5as tested
using (itmus !a!er# &hen+ a dro! o* 1:; HC( 5as added and
noted i* any gas e6o(6ed# Last(y+ the so(ution 5as tested *or
!resence o* meta( 5ith the use o* *(ame test in 5hich a nichrome
5ire 5as used#
&hen+ *or the So(ubi(ity C(assi*ication &ests+ the test
com!ounds 5ere buty( bromide+ ethano(+ sucrose+
butera(dehyde+ ethanoic acid+ methy(amine+ nitro !heno(+ diethy(
ether+ ben<oic acid+ !ro!anone+ and the !re6ious un4no5n
sam!(es tested in the *irst !art# 8or each o* these test
com!ounds+ they 5ere mi7ed 5ith 1 m( o* the so(6ent se!arate(y
as *o((o5s% 5ater+ ether+ :; HC(+ :; "aOH+ :; "aHCO3+ and
H2SO4# &hen+ tested 5hether so(ub(e or not# &he so(6ents 5ere
used in the com!ounds de!ending on the scheme !ro6ided in
the manua(# 8rom there+ the !ossib(e com!ounds are identi*ied
by means o* their so(ubi(ity c(ass# &hey 5ere a(so tested o* their
reaction 5ith (itmus !a!er and !heno(!htha(ein# &his 5as
!er*ormed in order *or the identi*ication o* the un4no5n
com!ounds gi6en#
R2S,3TS
Table *! 0ata or 4reliminary Tests
Compoun
ds
Copper
$itrate
Acetic
Acid
,n+no
wn *
,n+now
n '
)hysica(
state
So(id Li9uid Li9uid Li9uid
Co(or -(ue Co(or(ess Co(or(es
s
Co(or(ess
Odor Odor(ess Strong
sour sme((
Odor(es
s
-urned
!(astic-
(i4e sme((
.gnition
test
reen
*(ame
"o meta(
!resent
-(ue-
green
*(ame
"o meta(
!resent
Table '! 0ata or Solubility Tests
Compounds -uty(
bromide
,than
o(
Sucros
e
,thanoi
c acid
5ater = 3 3 3
2ther = 3 = 3
#Cl = = = =
$a%# = = = =
$a#C%& = = = =
#'S%( = = =
Reaction to
litmus
= "eutr
a(
= 'cidic
Reaction to
phenolphthalein
= = = =
Solubility Class $ Sn S Sa
Compounds Methy(
amine
"itro
!heno
>iethy(
ether
-utera(-
dehyde
Experiment 01 Group No. 8 January 21. 2014 2 of 4
CHM143L Organic Chemistry 2 Laboratory
3rd Quarter SY 2013-2014 rou! "o# $% &he '(coho(ics
(
5ater 3 = = =
2ther = = = =
#Cl = = = =
$a%# = = = =
$a#C%& = = = =
#'S%( = 3 3 =
Reaction to
litmus
= = = =
Reaction to
phenolphthalein
= = = =
Solubility Class S $ $ )
Compounds Ben6oic acid 4ropanone
5ater = 3
2ther = 3
#Cl = =
$a%# 3 =
$a#C%& 3 =
#'S%( = =
Reaction to
litmus
= "eutra(
Reaction to
phenolphthalein
= =
Solubility Class A* Sn
Table &! 0ata Regarding the ,n+nown Samples and the
4ossible Compounds
,n+now
n $o!
5ater 2ther #Cl $a%# $a#
C%&
#'S%(
7A 3 3 = = = =
7B = ------ = = ------ =
,n+nown $o! $' $-
Reaction to
litmus
= =
Reaction to
phenolphthalein
= =
Solubility Class Sn )
4ossible
Compounds
Mono*unctiona(
a(coho(s+ a(dehydes+
4etones+ amides+
esters+ aromatic
amines+ nitri(es+ and
amides 5ith *i6e
carbons or *e5er
Saturated
hydrocarbons+
ha(oa(4anes+ ary(
ha(ides+ other
deacti6ated
aromatic
com!ounds+
diary( ethers
3egend8
) 9 .nso(ub(e or not tested on the so(6ent indicated
3 . So(ub(e in the *o((o5ing so(6ent
Corrections8
-uty( bromide ? C(ass =
Sucrose ? C(ass =
-utera(dehyde ? C(ass Sn
Methy( amine ? C(ass -
"itro!heno( ? C(ass '1
>iethy( ether ? C(ass -
0"SC,SS"%$
&ab(e 1 tabu(ates the data regarding the !hysica( state+
co(or+ odor+ and ignition test o* the 4no5n and un4no5n
com!ounds# @sing co!!er nitrate as the test com!ound+ 5e can
obser6e that in using the ignition test+ a green *(ame !roduced#
8rom *(ame s!ectra e7!eriment+ the meta( it contains is co!!er#
&hen regarding the acetic acid+ it has a strong sour sme((+ in
5hich an acid readi(y !ossesses#
&ab(e 2 identi*ies the so(ubi(ity c(asses o* the 4no5n
com!ounds by manner o* 5hich they are so(ub(e or not in the
Experiment 01 Group No. 8 January 21. 2014 3 of 4
CHM143L Organic Chemistry 2 Laboratory
3rd Quarter SY 2013-2014 rou! "o# $% &he '(coho(ics
so(6ents tested# >i**erent com!ounds 5ith di**erent !ossib(e
so(ubi(ity c(asses 5ere used in order to readi(y identi*y the
un4no5n com!ounds gi6en# Some o* the com!ounds 5ere not
tested in certain so(6ents because o* the scheme *o((o5ed *or
easier identi*ication o* the so(ubi(ity c(ass and its !ossib(e
com!ounds# Aeaction o* the com!ound to (itmus is necessary i* it
is so(ub(e in ether in order to determine i* it contains acidic or
basic *unctiona( grou!s#
Aegarding the un4no5n sam!(es+ *or $'+ as the ignition
test 5as used+ it !roduced a b(ue-green *(ame indicating that it
contains a co!!er ha(ide# -ut as suggested by the so(ubi(ity test
!er*ormed+ it is C(ass Sn# &he error regarding this can !ossib(y be
due to the so(ubi(ity test because it is more !rone to commit
errors rather than the !re(iminary tests# Since it is a ha(ide as
identi*ied by the instructor+ it *a((s under the = C(ass#
&hen regarding the un4no5n sam!(e $-+ it *a((s a(so
under = as suggested by the so(ubi(ity test# &his is because
*o((o5ing the scheme *or so(ubi(ity c(ass identi*ication+ it is
inso(ub(e in the so(6ents tested# Li4e5ise in the !re(iminary test+ it
!roduced no residue as it 5as heated+ in*erring that there is no
meta( !resent in there# 8rom this+ the !ossib(e com!ounds are
simi(ar to that o* the $' un4no5n com!ound in 5hich it is an n-
a(i!hatic ha(ide as identi*ied by the instructor that *a((s under
ha(oa(4anes#
)ossib(e sources o* error regarding this e7!eriment
5ou(d most(y be because o* human error such as incorrect
obser6ation o* 5hether so(ub(e or not and the e7cess addition o*
the com!ound to be obser6ed in a certain so(6ent that may cause
obser6ation issues in terms o* so(ubi(ity !ro!erties o* the
com!ounds tested#
&his e7!eriment uti(i<es t5o ma2or tests in identi*ying
organic com!ounds% )re(iminary tests and So(ubi(ity
c(assi*ication+ then e7amines and identi*ies the un4no5n
com!ound3s by the use o* these tests in terms o* the so(ubi(ity
c(ass and *rom there+ the !ossib(e com!ounds#
>es!ite such errors made during the e7!eriment+
corrections 5ere considered and that the use o* the !re(iminary
tests and so(ubi(ity c(assi*ication thorough(y identi*ied the di**erent
characteristics o* organic com!ounds that resu(ted to incorrect
c(assi*ication# -ut on the other hand+ the ob2ecti6es o* the
e7!eriment 5ere achie6ed#
@sing the !re(iminary test+ the !hysica( state+ odor+
co(or+ and *(ame co(or by ignition test o* the 4no5n and un4no5n
com!ounds 5ere identi*ied# 8rom there+ some o* the
characteristics !ossessed by certain grou!s 5ere matched and
determined# &hen *or *urther determination+ the so(ubi(ity test 5as
used in 5hich 4no5n and un4no5n com!ounds 5ere tested in
di**erent so(6ents common(y used in order to identi*y
the so(ubi(ity c(ass and su!!ort it 5ith the data obtained *rom the
!re(iminary tests#
&his e7!eriment is 6ery critica( because the s4i((s
(earned here 5i(( be a!!(ied to the succeeding e7!eriments such
as reactions o* a(coho(s+ !heno(s+ a(dehyde+ 4etones+ and many
more# 8or a !(ausib(e recommendation regarding this
e7!eriment+ it 5ou(d be to care*u((y *o((o5 the !rocedures 5ritten
in the manua( and i* so the instructions gi6en by the instructor
regarding the e7!eriment# -e c(ear about 5hat obser6ations can
be seen and ma4e sure to note do5n these e6en the sma((est
detai( !ossib(e because it can !ossib(y be a su!!orting detai(
5hen it comes to the discussion !art#
R2/2R2$C2S
* Baluyut, :!;! < 0e Castro, =! Organic Chemistry Laboratory
Manual for Chemical Engineering Students Part 2.
' Qualitative Analysis of Organic Comounds. Retrieved /ebruary
', '>*( rom
http8??academics!wellesley!edu?Chemistry?chem'**lab?
%rgo@3ab@1anual?Appendix?ClassiicationTests?!
&

Experiment 01 Group No. 8 January 21. 2014 4 of 4