CHM143L Organic Chemistry 2 Laboratory

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

Carboxylic Acids and Their Derivatives
Martin, Marilen
1
, Taeda, John Paul, D., CHM14!"#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 utilized several chemical tests that can classify carboxylic acids and their derivatives. Carboxylic acids are
organic compounds usually characterized by at least one carboxyl group. A carboxyl group consists of a carbonyl (a carbon
atom double bonded to an oxygen atom and a hydroxyl (R!"!#. $reparation strategies can be performed in order to produce
functional derivatives of carboxylic acid such as acyl halides% anhydrides% amides% and esters. They can be classified through
several chemical tests li&e 'sterification Reactions% Acid and Base #ydrolysis% Anilide (ormation% #ydroxamic Acid Test%
Alcoholic Silver )itrate Test% and Sodium Bicarbonate Test. (rom each test% selected test compounds *ere used from the
follo*ing+ acetyl chloride% acetic acid% acetic anhydride% acetamide% and ethyl acetate. 'ach test *as aided *ith different
reagents necessary for observations such as color changes% evolution of heat and gases% and precipitate formations. Specific
tests *ere also accompanied by apparatuses% other than micro test tubes *ith cor& stoppers% droppers% and the li&e are reflux
condensers% *arm *ater bath% filter paper% ,-!ml 'rlenmeyer flas&% and hot plate. After performing the experiment%
analyzing.interpreting% and discussing the data gathered% the group *as able to achieve the ob/ectives listed in this
experiment since their data coincided *ith the theories discussed in this particular topic. The group *as also able to identify
the reactions that too& place% *hich helped them the nature of each test for each compound to be tested.
0)TR"12CT0")
Carbo4y(ic acids are organic com!ounds usua((y
characteri5ed by at (east one carbo4y( grou!# ' carbo4y( grou!
consists o* a carbony( 0a carbon atom doub(e bonded to an
o4ygen atom1 and a hydro4y( 06-O-H1# Carbo4y(ic acids ha7e a
genera( *ormu(a o* 6-COOH# 's !roton donors+ they are
characteri5ed as -ronsted-Lo8ry acids# &hey a(so act as both
hydrogen bond acce!tors 0due to the carbony( grou!1 and
hydrogen bond donors 0due to the hydro4y( grou!1+ (eading to
them o*ten !artici!ating in hydrogen bonding# Carbo4y(ic acids
are used as !recursors to *orm other com!ounds such as esters+
a(dehydes+ and 9etones by means o* synthetic strategies#
(igure 3. 4eneral Structure
of a Carboxylic Acid
.n terms o* the !ro!erties o* carbo4y(ic acids+ they ha7e
re(ati7e(y high boi(ing !oints com!ared to organic com!ounds
such as a(coho(s due to their hydrogen-bonding interactions# .n
addition to that+ carbo4y(ic acids are a(so more acidic than the
said re(ati7e organic com!ounds by a huge magnitude due to the
stabi(ity o* the con2ugate base+ 8hich is resonance stabi(i5ed
8hen de!rotonated# :rom the con2ugate base+ the negati7e
charge is de(oca(i5ed o7er t8o o4ygen atoms+ rendering it more
stab(e# &he acidity o* carbo4y(ic acids may be a**ected by the
nature o* the substituent !resent#
Carbo4y(ic acids undergo reactions such as sa(t
*ormation+ e(ectro!hi(ic substitution at o4ygen+ and substitution o*
hydro4y( grou!# :rom the substitution o* hydro4y( grou!+ it is
being re!(aced by another nuc(eo!hi(ic grou! 8here *rom there+
*unctiona( deri7ati7es o* carbo4y(ic acids are *ormed# 'cy(
ha(ides+ anhydrides+ and amides are some notab(e deri7ati7es o*
the said acids#
Carbo4y(ic acids and their deri7ati7es can be c(assi*ied
through numerous tests and reactions (i9e ,steri*ication
6eactions+ 'cid and -ase Hydro(ysis+ 'ni(ide :ormation+
Hydro4amic 'cid &est+ '(coho(ic Si(7er "itrate &est+ and Sodium
-icarbonate &est#
.n ,steri*ication 6eactions+ treatment o* a(coho( such as
ethano( is uti(i5ed in order to !roduce an ester+ 8hich has a s8eet
or *ruity odor indicating a !ositi7e resu(t o* the test# .n 'cid
Hydro(ysis+ addition o* 8ater ta9es !(ace resu(ting in a carbo4y(ic
acid and e7o(ution o* heat+ indicating that the reaction is
e4othermic and success*u(# :or *urther con*irmation+ the said acid
is treated 8ith saturated sodium carbonate so(ution and carbon
dio4ide gas e7o(7ed *rom the mi4ture# .n -ase Hydro(ysis+ the
Experiment 05 Group No. 8 March 4. 2014 1 of
6
CHM143L Organic Chemistry 2 Laboratory
3rd Quarter SY 2013-2014 rou! "o# $% &he '(coho(ics
com!ound is treated 8ith a strong base such as sodium
hydro4ide+ !roducing a sa(t o* a !articu(ar meta(# &his sa(t is
reacted 8ith hydrogen ion to !roduce carbo4y(ic acid# .n 'ni(ide
:ormation+ the com!ound is treated 8ith ani(ine to !roduce an
ani(ide !reci!itate# .n Hydro4amic 'cid &est+ the com!ound is
treated 8ith hydro4y(amine to !roduce hydro4amic acid+ *o((o8ing
by reaction 8ith *erric ch(oride so(ution in order to *orm a *erric
hydro4amate com!(e4# .n '(coho(ic Si(7er "itrate &est+ the
com!ound is *irst treated 8ith 8ater to yie(d carbo4y(ic acid+
*o((o8ed by si(7er nitrate in a(coho( to !roduce a so(id si(7er
carbo4y(ate sa(t that disso(7es u!on addition o* nitric acid# :ina((y+
*or Sodium -icarbonate &est+ the com!ound is treated sodium
bicarbonate to !roduce a sodium s(at o* the acid and carbon
dio4ide gas+ 8hich indicates a !ositi7e resu(t regarding the test#
.n this e4!eriment+ the a*orementioned tests are
!er*ormed *rom se(ected com!ounds *rom carbo4y(ic acid u! to
their deri7ati7es *or each test in order to identi*y 8hich test
determines 8hat !articu(ar com!ound is !resent and di**erentiate
them *rom their characteristic reactions#
5AT'R0A6S A)1 5'T#"1S

&he e4!eriment 8as !er*ormed by the use o* the
*o((o8ing a!!aratuses% 2 and ; m( !i!ets+ test tube rac9+ micro
test tubes 83 cor9 sto!!ers+ condenser+ ;0-m( ,r(enmeyer *(as9+
;0-m( bea9er+ hot !(ate+ iron stand+ 8arm 8ater bath+
thermometer+ dro!!ers+ and *i(ter !a!er# &hen+ the *o((o8ing
reagents 8ere uti(i5ed in the !er*ormance o* the e4!eriment%
g(acia( acetic acid+ acetic anhydride+ acety( ch(oride+
concentrated H2SO4+ abso(ute ethano(+ saturated "aHCO3+
methano(+ <M "aOH+ 10= CuSO4+ <M HC(+ 20= "aOH+ ;=
:eC(3+ acetamide+ ethy( acetate+ ani(ine+ 1M HC(+ >;= ethano(+
!ro!y(ene g(yco(+ 1M ?OH+ ;= H"O3+ 'g"O3 in ethano( so(ution+
1#0M hydro4y(amine hydroch(oride in >;= ethano(+ and
hydro4y(amine hydroch(oride so(ution in !ro!y(ene g(yco(# &he
e4!eriment consisted o* si4 !arts% ,steri*ication 6eactions+
Hydro(ysis+ 'ni(ide :ormation+ Hydro4amic 'cid &est+ '(coho(ic
Si(7er "itrate &est+ and Sodium -icarbonate &est#
&he *irst !art+ ,steri*ication 6eactions+ consisted o*
g(acia( acetic acid+ acetic anhydride+ and acety( ch(oride as test
com!ounds# :rom 10 dro!s o* each o* the said com!ound+ ;
dro!s o* conc# H2SO4 and 1 m( abso(ute ethano( 8ere added#
&hen using a steam bath+ the so(utions 8ere gent(y 8armed *or
about 3 minutes# &he odor and other obser7ations 8ere recorded
therea*ter#
&he second is ca((ed Hydro(ysis# &his !art consisted *or
t8o sub!arts% 'cid Hydro(ysis and -ase Hydro(ysis# :or the 'cid
Hydro(ysis+ the test com!ounds 8ere acety( ch(oride and acetic
anhydride# &hree dro!s o* each test com!ound 8as added to 1
m( 8ater in se!arate micro test tubes+ then tested i*
heat has e7o(7ed# 1 m( o* methano( and saturated "aHCO3
so(ution 8as added a*ter that and obser7ations 8ere recorded#
&he second sub!art+ -ase Hydro(ysis+ uti(i5ed acetamide and
ethy( acetate as the test com!ounds 8ith se!arate !rocedures#
:or acetamide+ 0#20 m( o* it 8as added 4 m( o* <M "aOH in a ;0-
m( bea9er# ' *i(ter !a!er added 8ith 2 dro!s o* 10= CuSO4 8as
!(aced on to! o* the bea9er# &he mi4ture 8as boi(ed *or about a
minute and the co(or change o* the so(ution in the *i(ter !a!er and
the odor o* the mi4ture 8ere noted# '*ter that+ the mi4ture 8as
acidi*ied by the addition o* <M HC( so(ution *or *urther test
!ur!oses#&hen *or ethy( acetate+ 4 m( o* it and ; m( o* 20=
"aOH 8as added in a ;0-m( ,r(enmeyer *(as9# ' condenser 8as
*itted in the said *(as9 and re*(u4 8as !er*ormed *or 1; minutes
and the a!!earance o* the mi4ture be*ore and a*ter re*(u4 8as
com!ared# &he mi4ture then 8as neutra(i5ed 8ith HC(+ *o((o8ed
by the addition o* a *e8 dro!s o* :eC(3 so(ution+ and the co(or
8as noted#
&he third !art 8as about ani(ide *ormation# &he test
com!ounds used 8ere acety( ch(oride and acetic anhydride# 0#20
m( o* each o* the test com!ounds 8ere !(aced in se!arate micro
test tubes *o((o8ed by 1 m( o* ani(ine and 4 m( disti((ed 8ater#
Obser7ations 8ere ta9en do8n a*ter that#
&he *ourth !art o* the e4!eriment is ca((ed Hydro4amic
'cid &est# &8o !rocedures 8ere *o((o8ed here/ one *or acety(
ch(oride+ acetic anhydride+ and ethy( acetate as the test
com!ounds and another *or acetamide as the test com!ound#
:or the *irst !rocedure+ 0#10 m( o* each test com!ound 8as
mi4ed 8ith 0#20 m( o* 1#0M hydro4y(amine hydroch(oride in >;=
ethano( and 0#20 m( o* <M "aOH# &he mi4tures 8ere boi(ed and
a((o8ed to coo( *or a minute+ *o((o8ed by the addition o* 2#0 m( o*
1#0M HC(# :or c(oudy so(utions+ >;= ethano( 8as added unti( the
so(ution is c(ear# Last(y+ ;= :eC(3 8as added dro! by dro! unti( a
distinct co(or 8as obser7ed# Obser7ations 8ere recorded
therea*ter# &hen *or the other !rocedure+ 0#10 m( o* acetamide
8as disso(7ed in about 1 m( o* !ro!y(ene g(yco(# &hen+ 1#;0 m( o*
hydro4y(amine hydroch(oride so(ution and 0#@; m( o* 1#0 M ?OH
8as added# &he mi4ture 8as boi(ed *or 2 minutes under
moderate heat and it 8as coo(ed a*ter# ;= :eC(3 8as dro!8ise
added unti( a distinct co(or is obser7ed#
&he *i*th !art is about '(coho(ic si(7er nitrate test# &he
test com!ounds 8ere acety( ch(oride and acetic acid# 0#20 m( o*
each o* the test com!ounds 8ere added in se!arate micro test
tubes then 2#0 m( o* 'g"O3 in ethano( so(ution 8ere added to
each test tube# Since !reci!itates *ormed+ 3 dro!s o* ;= H"O3
8ere added to both so(utions and noted 8hether the !reci!itate
has disso(7ed or not#
Experiment 05 Group No. 8 March 4. 2014 2 of
6
CHM143L Organic Chemistry 2 Laboratory
3rd Quarter SY 2013-2014 rou! "o# $% &he '(coho(ics
&he si4th and (ast !art 8as about Sodium bicarbonate
test# 'cetid acid+ as the test com!ound+ 8as disso(7ed in 1#0 m(
methano( in a micro test tube# &hen+ 1#0 m( o* saturated "aHCO3
so(ution 8as added and obser7ation 8ere recorded a*ter that#
R'S26TS A)1 10SC2SS0")
0. 'sterification Reactions
Table 3. "bservations of Test Compounds in $art 0
Test Compounds "bservations
(acia( acetic acid 011 )(astic ba((oon-(i9e sme((
'cetic anhydride 021 )(astic ba((oon-(i9e sme((
'cety( ch(oride 031 )(astic ba((oon-(i9e sme((/ gas e7o(7ed
8ith the addition o* H2SO4
Table 7. Reactions 0nvolved in $art 0.
Reactions 0nvolved
(3
O
C H
3 OH
C H
3 OH
+
c o n c . H
2
S O
4
O
C H
3 O CH
3
+
O H
2
(7
O
C H
3 O CH
3
O
C H
3 OH
+
c o n c . H
2
S O
4
O
C H
3 O CH
3
+
O
C H
3 OH
(8
O
C H
3
Cl
C H
3 OH
+
c o n c . H
2
S O
4
O
C H
3 O CH
3
+ Cl H
Carbo4y(ic acid+ acid ha(ides+ and acid anhydrides 8ere
identi*ied 8ith the use o* ester *ormation using ethano( as the
a(coho(# :rom the obser7ations recorded in this !art+ a(( test
com!ounds indicate a !(astic ba((oon-(i9e sme(( a*ter reacting
8ith ethano(+ 8hich in*ers that a ester 8as *ormed not on(y *rom
the e7o(ution o* a *ruity odor+ but *rom a rather !(easant sme((#
,sters are *ormed *rom these com!ounds *irst by means
o* !rotonating the carbony( o4ygen by the conc# H2SO4 in order
*or the ethano( to attac9 the carbony( carbon due to it being a
8ea9 nuc(eo!hi(e because it is a neutra( com!ound# '*ter
attac9ing+ intramo(ecu(ar !roton trans*er occurs in order to ha7e
8ater as a (ea7ing grou! because a hydro4ide grou! is a bad
(ea7ing grou!# &he (one !air o* o4ygen *rom the ethano(
substituent !ushes the 8ater out o* the com!ound then *o((o8ed
by de!rotonation in order to *orm the desired ester together 8ith
a by-!roduct de!ending on the carbo4y(ic acid deri7ati7e#
00. #ydrolysis
Table 8. "bservations of Test Compounds in $art
00
Test
Compounds
"bservations
'cetic
anhydride
011 :ormation o* bubb(es 8as obser7ed/ c(ear
so(ution 8ith no heat e7o(7ed 8as
!roduced3resu(ted
'cety(
ch(oride
021 :ormation o* bubb(es 8as obser7ed/ c(ear
so(ution 8ith heat e7o(7ed resu(ted
'cetamide 031 &he co(or o* CuSO4 so(ution in the *i(ter !a!er
became intense b(ue/ so(ution has a strong+ *ou(
sme((/ gas e7o(7ed 8ith the addition o* <M HC(
,thy( acetate 041 &he resu(ting mi4ture !roduce is c(ear orange
Table 9. Reactions 0nvolved in $art 00.
Reactions 0nvolved
(3
C H
3
O
O
O
CH
3
O H
2
C H
3
O
OH
C H
3
O
OH
+
h e a t
NaHCO
3
C H
3
O
O
-
Na
+
+
O H
2 +
CO
2
(g)
+
2
(7
C H
3
O
Cl
O H
2
C H
3
O
OH
+
Cl H
C H
3
O
OH
+ h e a t
NaHCO
3
C H
3
O
O
-
Na
+
+
O H
2 +
CO
2
(g)
(8
C H
3
O
NH
2
NaOH
C H
3
O
O
-
+
+
Na
+
NH
3
Na
+
C H
3
O
O
-
+
H
+
C H
3
O
OH
+
Na
+
(9
Experiment 05 Group No. 8 March 4. 2014 3 of
6
CHM143L Organic Chemistry 2 Laboratory
3rd Quarter SY 2013-2014 rou! "o# $% &he '(coho(ics
+
O
C H
3
O
-
+
O
C H
3
O CH
3
NaOH
Na
+
Na
+
O
C H
3
O
-
+
H
+
O
C H
3
OH
+
C H
3
CH
3
Na
+
.n terms o* acid hydro(ysis+ acid anhydrides and acy(
ha(ides undergo hydro(ysis to !roduce carbo4y(ic acid and heat+
8hich denotes that this is an e4othermic reaction# &he mi4ture is
*urther reacted 8ith saturated sodium carbonate and !roduces
carbon dio4ide gas *or con*irmation o* the !resence o* carbo4y(ic
acid# &hen in terms o* base hydro(ysis+ amide and esters
undergo this# :or amides+ the co(or o* the co!!er su(*ate so(ution
on the *i(ter !a!er *urther intensi*ies the b(ue co(or as the mi4ture
8as boi(ed# Mean8hi(e *or esters+ the *ormation o* a
homogeneous mi4ture is obser7ed# :or a(( the a*orementioned
carbo4y(ic acid deri7ati7e test com!ounds+ !ositi7e resu(ts 8ere
in*erred *rom them based on the obser7ations recorded on &ab(e
3+ meaning that the hydro(ysis test that each o* the carbo4y(ic
acid deri7ati7es under8ent 8ere e**ecti7e in c(assi*y these
!articu(ar com!ounds#
:or acid hydro(ysis+ the com!ound is added 8ith a
hydro4ide grou! 8hi(e the (ea7ing grou! that 8as !ushed is
added 8ith a hydrogen ion# .n the case o* acetic anhydride+ both
the ma2or !roduct and by-!roduct is an acetic acid+ gi7ing it t8o
eAui7a(ents# .n the case o* acety( ch(oride+ the ma2or !roduct is
acetic acid 8hi(e the by-!roduct is hydrogen ch(oride# &he acetic
acid !roduced is to react 8ith sodium carbonate *or con*irmation
!ur!oses#
&hen *or base hydro(ysis+ the com!ound is added 8ith
sodium hydro4ide in order to *orm a sodium sa(t 8ith a certain by-
!roduct de!ending on the (ea7ing grou!# &hen+ the sodium in the
sa(t is re!(aced 8ith a hydrogen ion+ !roducing a carbo4y(ic acid
a(ong 8ith a sodium ion#
000. Anilide (ormation
Table ,. "bservations of Test Compounds in $art 000
Test Compounds "bservations
'cetic anhydride 011 .nso(ub(e mi4ture 8as !roduced 8ith
u!!er (ayer 8ater 0c(ear1 and (o8er (ayer
orange# "o gas e7o(7ed *rom the addition o*
ani(ine#
'cety( ch(oride 021 as e7o(7ed as ani(ine 8as dro!!ed
into the test com!ound resu(ted into an
inso(ub(e mi4ture
Table :. Reactions 0nvolved in $art 000
Reactions 0nvolved
(3
+
O
C H
3
NH
O
C H
3 O CH
3
O
NH
2
2
+
O
C H
3
O
-
N H
3
+
(7
+
O
C H
3
NH
O
C H
3
Cl
NH
2
2
+
N H
3
+
Cl
-
'ni(ide *ormation is a test 8herein a nuc(e!hi(ic addition-
e(imination reaction is obser7ed+ *orming an ani(ide !reci!itate#
:rom the obser7ations+ both anhydride and acy( ha(ide as the
test com!ounds *ormed a !reci!itate 8hen reacted 8ith ani(ine+
indicating a !ositi7e resu(t in the test#
&he *irst stage o* ani(ide *ormation in7o(7es a
nuc(eo!hi(ic attac9 on the carbony( carbon by the (one !air o* the
nitrogen atom on the ani(ine and simu(taneous to that+ the
o4ygen brea9s the carbony( doub(e bond# &his ser7es as the
addition stage o* the reaction# &he second stage in7o(7es a
carbony( re*ormation 8here the o4ygen atom re*orms the doub(e
bond 8ith the carbon atom and the substituent 0the ch(oride atom
*rom acid ha(ide+ *or e4am!(e1 is !ushed o**# &his ser7es as the
e(imination stages o* the reaction# &he hydrogen ion *rom the
ani(ine that attac9ed is remo7ed by an ani(ine mo(ecu(e+ *orming
the desired ani(ide#
0;. #ydroxamic Acid Test
Table <. "bservations of Test Compounds in $art 0;
Test Compounds "bservations
'cetic anhydride 011 C(ear so(ution a*ter addition o* "aOH/
homogeneous magenta so(ution a*ter
addition o* ;= :eC(3
'cety( ch(oride 021 Bhite !reci!itate *ormed a*ter addition
o* "aOH/ homogeneous magenta so(ution
a*ter addition o* ;= :eC(3
'cetamide 031 C(ear so(ution a*ter addition o* "aOH/
orange so(ution 8ith the dar9er co(or o* it
sett(ed at the bottom 8as !roduced as ;=
:eC(3
,thy( acetate 041 C(ear so(ution a*ter addition o* "aOH/
homogeneous magenta so(ution a*ter
addition o* ;= :eC(3
Table =. Reactions 0nvolved in $art 0;
Experiment 05 Group No. 8 March 4. 2014 4 of
6
CHM143L Organic Chemistry 2 Laboratory
3rd Quarter SY 2013-2014 rou! "o# $% &he '(coho(ics
Reactions 0nvolved
(3
O CH
3
C H
3
O O
+
N H
2
OH
C H
3
O
NH OH
+
OH C H
3
O
C H
3
O
NH OH
+
eCl
3
C H
3
O
NHO
3
e
+
Cl H 3
(7
C H
3
O
Cl
+
N H
2
OH
C H
3
O
NH OH
+
C H
3
O
NH OH
+
eCl
3
C H
3
O
NHO
3
e
+
Cl H 3
Cl H
(8
+
O
C H
3
NH
2
+
Cl H
eCl
3
O
C H
3
NH
2
3
e
(9
O C H
3
O
CH
3
+
N H
2
OH
C H
3
O
NH OH
+
C H
3
OH
C H
3
O
NH OH
+
eCl
3
C H
3
O
NHO
3
e
+
Cl H 3
Hydro4amic 'cid &est is accom!anied by a *erric
ch(oride so(ution 8herein reacting 8ith the carbo4y(ic acid
deri7ati7e+ a *erric hydro4amate com!(e4 is !roduced in the *orm
o* a magenta or burgundy co(or# .n the case o* amides+ an
orange co(or in the mi4ture 8ou(d be obser7ed# -ased on the
obser7ations recorded on &ab(e @+ !ositi7e resu(ts 8ere !roduced
out o* the !er*ormance o* the said test#
Simi(ar to 'ni(ide :ormation+ this !articu(ar test in7o(7es
a nuc(eo!hi(ic addition-e(imination reaction 8herein the (one !air
o* the nitrogen atom in the hydro4y(amine grou! attac9s the
carbony( carbon and simu(taneous(y by the brea9ing o* the
carbony( doub(e bond# .t is then *o((o8ed by the e(imination o* the
substituent origina((y *rom the carbo4y(ic acid deri7ati7e by
means o* bringing the carbony( doub(e bond bac9# :rom the
hydro4amic acid *ormed+ *ormation o* the *erric
hydro4amate com!(e4 is !er*ormed by reacting it 8ith *erric
ch(oride#
;. Alcoholic Silver )itrate Test
Table >. "bservations of Test Compounds in $art ;
Test Compounds "bservations
'cetic acid 011 Mi(d c(oudy so(ution 8as !roduced 8ith
7ery sma(( !reci!itates# &he !reci!itates did
not disso(7ed 8ith the addition o* ;= H"O3
at *irst+ but a*ter some time+ it disso(7ed#
'cety( ch(oride 021 C(oudy 8hite so(ution 8as !roduced
8ith *ormation o* 8hite !reci!itate# 's ;=
H"O3 8as added+ the !reci!itates
disso(7ed#
Table 3-. Reactions 0nvolved in $art ;
Reactions 0nvolved
(3
+
O
C H
3
OH
+
HNO
3
!gNO
3
O
C H
3
O
-
!g
+
(7
C H
3
O
Cl
O H
2
C H
3
O
OH
+
Cl H
C H
3
O
OH
+
!gNO
3
C H
3
O
O
-
!g
+
+
HNO
3
'(coho(ic si(7er nitrate test is used to determine the
!ossibi(ity o* an un9no8n com!ound being an acid ha(ide or a
carbo4y(ic acid# :rom the obser7ations recorded on &ab(e >+ both
test com!ounds e4hibit a !reci!itate *ormation using the said test
and that the !reci!itates 8ere disso(7ed by the addition o* nitric
acid so(ution# &his indicates that a !ositi7e test resu(t is e7ident
due to the *ormation o* the so(id si(7er carbo4y(ate sa(t that
disso(7es u!on nitric acid addition#
&he said sa(t is *ormed by the reaction o* acetic acid
8ith si(7er nitrate# &his is disso(7ed by the addition o* nitric acid#
.n the case o* acety( ch(oride+ it *irst undergo nuc(eo!hi(ic
addition-e(imination 8ith 8ater to !roduce acetic acid 8ith
hydrogen ch(oride as the by-!roduct# &hen+ the acetic acid is
then reacted 8ith si(7er nitrate#
Experiment 05 Group No. 8 March 4. 2014 5 of
6
CHM143L Organic Chemistry 2 Laboratory
3rd Quarter SY 2013-2014 rou! "o# $% &he '(coho(ics
;0. Sodium Bicarbonate Test
Table 33. "bservation and Reaction 0nvolved of Acetic Acid
in $art ;0
Test
Compound
'cetic acid
"bservation 's the sodium bicarbonate so(ution 8as added
to the so(ution containing acetic acid and
methano(+ bubb(es 8ere *ormed#
Reaction
0nvolved
OH C H
3
O
+
NaHCO
3
O
-
C H
3
O
Na
+
+ O H
2 + CO
2
Sodium bicarbonate test is used to determine the
!resence o* a carbo4y(ic acid# :rom the reaction o* acetic
anhydride in carbo4y(ic acid+ there obser7ed 0recorded in &ab(e
111 a *ormation o* bubb(es+ 8hich indicates the e7o(ution o*
carbon dio4ide gas and sho8s a !ositi7e test resu(t#
Sodium bicarbonate so(ution is the most use*u( in
determining the !resence o* a carbo4y(ic acid because it has one
o* the most e7ident reactions 0e7o(ution o* carbon dio4ide gas1
and that e7en *rom 7arious mi4tures+ as (ong as it contains a
carbo4y(ic acid+ it 8i(( readi(y react 8ith sodium bicarbonate u!on
addition o* it# &his is used in the 'cid Hydro(ysis !art o* the
e4!eriment to con*irm i* a reaction has ta9en !(ace 8here a
carbo4y(ic acid is the !roduct#

C")C62S0")
&his e4!eriment identi*ies chemica( tests that can be
used in c(assi*ying carbo4y(ic acids and their deri7ati7es and
e4!(ain the chemica( basis o* each test used to c(assi*y these#
&his e4!eriment a(so di**erentiates carbo4y(ic acids and their
deri7ati7es such as acy( ha(ides+ anhydrides+ esters+ and amides
based on their characteristic reactions#
Carbo4y(ic acids are organic com!ounds that are 9no8n
*or their carbony( and hydro4y( grou!s !resent and because o*
this+ they are considered as both hydrogen bonding acce!tors
and donors# &hese acids are a(so !recursors in order to *orm
di**erent com!ounds and im!ortant to *orm deri7ati7es *unctiona(
grou!s (i9e acy( ha(ides+ anhydrides+ esters+ and amides# Se7era(
tests and reactions 8ere uti(i5ed in order to c(assi*y these
!articu(ar com!ounds such as ,steri*ication 6eactions+ 'cid and
-ase Hydro(ysis+ 'ni(ide :ormation+ Hydro4amic 'cid &est+
'(coho(ic Si(7er "itrate &est+ and Sodium -icarbonate &est#
Carbo4y(ic acids+ acy( ha(ides+ and acid anhydrides *orm
esters 8hen they react 8ith ethano( as the a(coho(+ 8hich is used
to identi*y the said com!ounds#
Carbo4y(ic acid deri7ati7es undergo hydro(ysis u!on the
addition o* 8ater and some heat# 'cid anhydrides and acy(
ha(ides undergo acid hydro(ysis in order to !roduced carbo4y(ic
acid and heat# ,7o(ution o* carbon dio4ide gas u!on addition o*
saturated sodium carbonate so(ution indicates the con*irmation o*
a !ositi7e resu(t regarding it# 'mides and esters undergo base
hydro(ysis 8here *or amides+ the a!!earance o* a b(ue co(or on
the *i(ter !a!er usua((y indicates a !ositi7e resu(t 8hi(e *or esters+
a *ormation o* a homogeneous mi4ture and the disa!!earance o*
the esterCs s8eet odor is obser7ed#
:rom 'ni(ide :ormation+ acid anhydrides and acy(
ha(ides undergo nuc(eo!hi(ic addition-e(imination 8ith ani(ine in
order to *orm an ani(ide !reci!itate#
'cid anhydrides+ acy( ha(ides+ esters+ and amides can
be c(assi*ied under Hydro4amic 'cid &est 8here the addition o*
*erric ch(oride so(ution is needed to *orm a *erric hydro4amate
com!(e4# ' !ositi7e resu(t is indicated by the *ormation o* a
burgundy or magenta co(or e4ce!t *or amides 8here the
indication is on the *ormation o* red to orange co(or in the
reaction mi4ture#
'(coho(ic Si(7er "itrate &est is used to identi*y an
un9no8n com!ound either being an acid ha(ide or a carbo4y(ic
acid+ 8here 8hen reacted 8ith si(7er nitrate in ethano( so(ution+ a
*ormation o* !reci!itate 0so(id si(7er carbo4y(ate sa(t1 is obser7ed
that is readi(y disso(7ed u!on the addition o* nitric acid#
Last(y+ sodium bicarbonate is used to determine the
!resence o* a carbo4y(ic acid 8here *ormation o* bubb(es
0e7o(ution o* carbon dio4ide gas1 indicate a !ositi7e resu(t#
R'('R')C'S
3 Baluyut% ?.@. A 1e Castro% B. "rganic Chemistry 6aboratory
5anual for Chemical 'ngineering Students $art 7.
7 Blein% 1. R. "rganic Chemistry% ?ohn Ciley A Sons% 0nc. Chapter
38+ Alcohols and $henols% (p.,:,!:73
8 $arsons% A. (. (7-38. Beynotes in "rganic Chemistry% 7
nd
edition.
7-39.
9 5c5urry% ?ohn (7--8. (undamentals of "rganic Chemistry (ifth
'dition. 0thaca% )@+ Cornell 2niversity.

Experiment 05 Group No. 8 March 4. 2014 6 of
6