CHM143L Organic Chemistry 2 Laboratory

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

Alcohols and Phenols
Martin, Marilen
1
, Taeda, John Paul, D., CHM143L/B31

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 examined and differentiated the properties of alcohols and phenols mainly on their structures and visualized
their characteristic reactions. Alcohols are molecules possessing the hydroxyl functional group (-!" to a car#on atom of an
al$yl %hereas phenols contain the same functional group #ut attached directly to an aromatic ring. Alcohols can #e classified
as primary& secondary& and tertiary depending on the num#er of al$yl groups attached on the car#on atom #earing the
hydroxyl group and this affect the different physical properties of alcohols. These can also #e transformed to different
functional groups depending on the reagents used and the reaction conditions. 'n this experiment& several %ere used for this
purpose such as Solu#ility test& Acidity(Basicity& Reaction %ith Sodium& Reaction %ith Acetyl Chloride& )ucas test& xidation&
'odoform test& Bromine *ater test& and +erric Chloride test. The test compounds mainly used for this %ere n-#utyl alcohol&
sec-#utyl alcohol& tert-#utyl alcohol& phenol& and #enzyl alcohol. #servations such as color of solution& its odor& time of
reaction& and other evidences of reaction changes %ere noted and from there& the reactions involved %ere %ritten do%n and
analyzed. After interpretation of the data gathered& the group %as a#le to visualize the reactions possi#le for alcohols and
phenols& o#serve their solu#ility and acidic properties& distinguish alcohols from phenols %ith the use of ferric chloride test&
oxidize alcohols into aldehydes& car#oxylic acids& and $etones depending on it structure& form al$yl chloride %ith the of the
)ucas reagent& form esters #y reacting it %ith acetyl chloride& determine activated aromatic groups %ith #romine %ater test&
and much more despite some human errors regarding this experiment.
',TR-.CT',
'(coho(s are mo(ecu(es containing the hydro4y(
*unctiona( grou! 0-OH1 that is bonded to a carbon atom o* an
a(5y( or substituted a(5y( grou!# Mean6hi(e+ !heno(s are
mo(ecu(es that contain a hydro4y( *unctiona( grou! that is direct(y
bonded to one o* the carbons in an aromatic ring# &he hydro4y(
*unctiona( grou! strong(y contributes to the !hysica( !ro!erties o*
a(coho(s because o* the in*(uence o* the hydrogen bonding abi(ity
o* it# One e4am!(e o* an a(coho( is methano(+ 6hich it is the
sim!(est a(coho(#
/
+igure 0. 1ethanol +igure 2. 3henol
&he so(ubi(ity and boi(ing !oint o* an a(coho( are a**ected
by the (ength o* the carbon chain and the sha!e o* the mo(ecu(e#
.n genera( a mo(ecu(e 6hich is more com!act or more branched
6i(( be more so(ub(e in 6ater# Li5e 6ater+ a(coho(s are 6ea5
-ronsted bases and 6ea5 -ronsted acids# &he nature o* the
a(5y( grou! can signi*icant(y in*(uence the basicity or the acidity#
Other *actors in*(uencing the acidity o* a(coho(s and !heno(s are
resonance+ induction+ and so(7ation e**ects#
'n a(coho( can be designated into a !rimary+ secondary
or tertiary a(coho( de!ending on the number o* a(5y( grou!s that
are attached to the carbon atom bearing the hydro4y( grou!#
,ach o* these di**er in terms o* !hysica( !ro!erties#
'(coho(s and !heno(s can be !recursors in order to
!roduce much more com!ounds out o* it by using the necessary
reagents in order to ha7e a certain desired !roduct#
.n order to be ab(e to ana(yse and demonstrate the
di**erent !ro!erties mentioned about a(coho(s and !heno(s+
se7era( tests 6i(( be used and they are as *o((o6s% So(ubi(ity test+
'cidity3-asicity+ 8eaction 6ith Sodium+ 8eaction 6ith 'cety(
Ch(oride+ Lucas test+ O4idation+ .odo*orm test+ -romine 9ater
test+ and :erric Ch(oride test#
&his e4!eriment uti(i;es the 7arious tests mentioned
!re7ious(y in order to e4amine the !ro!erties o* a(coho(s and
!heno(s and 7isua(i;e their characteristics reactions 6ith di**erent
reagents#
Experiment 03 Group No. 8 February 11. 2014 1 of
6
CHM143L Organic Chemistry 2 Laboratory
3rd Quarter SY 2013-2014 rou! "o# $% &he '(coho(ics
1AT4R'A)S A,- 14T!-S

&his e4!eriment consisted o* t6o main !arts% So(ubi(ity
and &est *or '(coho( and )heno(# &hen the (atter has eight
sub!arts% 'cidity3-asicity+ 8eaction 6ith Sodium+ 8eaction 6ith
'cety( Ch(oride+ Lucas &est+ O4idation+ .odo*orm &est+ -romine
9ater+ and :eC(3 &est# &he a!!aratuses used 6ere 2 < =-mL
!i!ets+ dro!!ers+ !H !a!ers+ thermometers+ test tube rac5s+
-unsen burner+ hot !(ate (itmus !a!er+ micro test tubes 6ith cor5
sto!!ers+ 6ater bath+ and a (ighted s!(inter#
&he *irst main !art is ca((ed So(ubi(ity# &he test
com!ounds 6ere ethy( a(coho(+ n-buty( a(coho(+ sec-buty( a(coho(+
tert-buty( a(coho(+ ben;y( a(coho(+ g(ycero(+ and !heno(# 0#=0 m( or
0#=0 g o* these com!ounds 6ere added to se!arate micro test
tubes# &hen+ 1 m( o* 6ater 6as added to each and *or those that
resu(ted in c(oudiness+ dro!6ise addition o* 6ater 6as !er*ormed
unti( a homogeneous obtained# >ata 6ere recorded 6hether or
not these com!ounds are so(ub(e in 6ater# &he test tubes *or
ethy( a(coho( and !heno( 6ere then reser7ed *or the ne4t !art#
&he second main !art is ca((ed &est *or '(coho( and
)heno(# &his consists o* eight !arts# &he *irst is ca((ed
'cidity3-asicity# &he test com!ounds here 6ere the ethy( a(coho(
and !heno( so(ution used in !art .# &he t6o o* them 6ere tested
*or reaction 6ith b(ue (itmus !a!er and !H !a!er# :rom the (itmus
!a!er+ there determined 6hether the so(ution is acidic or basic
then *rom the !H !a!er+ the a!!ro4imate !H 7a(ue 6as
determined# &hese 6ere recorded a*ter then#
&he second !art is ca((ed 8eaction 6ith Sodium# &he
test com!ounds 6ere n-buty( a(coho(+ sec-buty( a(coho(+ tert-buty(
a(coho(+ and !heno(# :rom se!arate test tubes 6ith 2 m( 0(i?uid1
or 0#=0 g 0so(id1 o* the test com!ounds+ a sma(( !e((et o* sodium
meta( 6as added and *rom there+ the rate o* gas e7o(ution 6as
recorded and com!ared# &he gas e7o(7ed 6as tested using a
(ighted s!(inter and -unsen burner# Obser7ations regarding this
6ere recorded#
&he third !art is ca((ed 8eaction 6ith 'cety( Ch(oride#
&he test com!ounds 6ere ethy( a(coho( and !heno(# .n se!arate
micro test tubes+ = dro!s o* ethy( a(coho( and a !inch o* !heno(
crysta(s 6ere added# &hen 3 @ 4 dro!s o* acety( ch(oride 6ere
added# &he mi4ture 6as a((o6ed to stand *or a *e6 minutes and
then 1 m( o* disti((ed 6ater 6as added# Obser7ations 6ere then
recorded#
&he *ourth !art is ca((ed Lucas test# &he test com!ounds
6ere n-buty( a(coho( sec-buty( a(coho(+ and tert-buty( a(coho(# .n
se!arate micro test tubes+ 2 m( o* Lucas reagent 6as added#
&hen+ 3 @ 4 dro!s o* the test com!ounds 6ere added to each test
tube simu(taneous(y and then they 6ere sha5en# &he
mi4tures 6ere a((o6ed to stand *or 10 @ 1= minutes 6ith minute(y
chec5ing# Obser7ations 6ere recorded therea*ter#
&he *i*th !art is ca((ed O4idation# &he test com!ounds
6ere ethy( a(coho(+ iso!ro!y( a(coho(+ and tert-buty( a(coho(# =
dro!s o* the test com!ounds 6ere added to se!arate micro test
tubes then 10 dro!s o* di(ute su(*uric acid and t6o dro!s o* 10A
B2Cr2OC so(ution 6ere added to each# &he co(or o* the so(ution
and its odor 6ere recorded a*ter that#
&he si4th !art is ca((ed# .odo*orm &est# &he test
com!ounds 6ere ethy( a(coho( and iso!ro!y( a(coho(# = dro!s o*
these com!ounds 6ere added to se!arate micro test tubes
*o((o6ed by = dro!s o* 4M "aOH# &hen+ a iodine in !otassium
iodide 6as added dro!6ise unti( a !a(e ye((o6 co(or !ersisted#
&he mi4ture 6as 6armed in a 6ater bath at D0C using a hot
!(ate# &he mi4ture 6as set aside *or se7era( minutes then
obser7ed#
&he se7enth !art is ca((ed -romine 9ater# &he test
com!ounds 6ere !heno( and ben;y( a(coho(# .n se!arate micro
test tubes+ a !inch o* !heno( crysta(s and *e6 dro!s o* ben;y(
a(coho( 6ere added# &he !heno( crysta(s 6ere disso(7ed in 1 m(
o* 6ater# &hen *or the t6o test tubes+ saturated bromine 6ater
6as added dro!6ise unti( a change 6as obser7ed#
&he eighth and (ast !art is ca((ed :eC(3# &he test
com!ounds 6ere !heno( and ben;y( a(coho(# .n t6o micro test
tubes+ = dro!s o* 10A :eC(3 so(ution 6as added#3 dro!s o*
ben;y( a(coho( 6as added to one test tube and 1 crysta( o*
!heno( to the other# &he resu(ts 6ere obser7ed and com!ared#
R4S.)TS
'. Solu#ility
Ta#le 0. Solu#ility of -ifferent Alcohol Compounds in *ater
Compound Solu#le 'nsolu#le
,thy( a(coho( (
n-buty( a(coho( (
sec-buty( a(coho( (
tert-buty( a(coho( (
-en;y( a(coho( (
(ycero( (
)heno( (
Correction5 6lycerol should #e solu#le
'n a(coho( is made o* t6o regions% the hydro!hobic and
hydro!hi(ic regions# Hydro!hobic regions are usua( the (ong
Experiment 03 Group No. 8 February 11. 2014 2 of
6
CHM143L Organic Chemistry 2 Laboratory
3rd Quarter SY 2013-2014 rou! "o# $% &he '(coho(ics
carbon chains that are readi(y inso(ub(e in 6ater 6hi(e the
hydro!hi(ic region is 6here so(ubi(ity in 6ater is obser7ed+ in
6hich they are usua((y hydro4y( grou!s and acy( chains# :rom
&ab(e 1+ ethy( a(coho(+ n-buty( a(coho(+ sec-buty( a(coho(+ and tert-
buty( a(coho( are so(ub(e in 6ater because they !ossess sma((
hydro!hobic regions 6hich causes them to be so(ub(e in 6ater#
''. Test for Alcohol and 3henol
a. Acidity(Basicity
Ta#le 2. Reaction of 4thyl Alcohol and 3henol to )itmus
3aper and p! 3aper
Compound Rxn %ith
litmus paper
Rxn %ith p!
paper
)iterature
7alue
,thy( a(coho( "o reaction C C
)heno( -(ue to red D = - D
'(coho(s are a(so 5no6n to be acidic because o* the
!resence o* a stab(e con2ugate base# .ts stabi(ity is readi(y
caused by the resonance stabi(ity and inducti7e e**ects o* the
o4ygen atom main(y because o* its (one !airs# :rom &ab(e 2+ both
the ethy( a(coho( and !heno( shou(d ma5e the co(or o* the b(ue
(itmus !a!er change to red and ha7e an acidic reaction 6ith the
!H !a!er# &he (iterature 7a(ue denotes the a!!ro4imate range o*
!H o* that !articu(ar a(coho( it shou(d ha7e+ in other 6ords+ the
true 7a(ue o* the !H# Sources o* errors are !ossib(y due to
human error such as the incorrect addition o* reagents needed
*or that !articu(ar !art o* e4!eriment#
#. Reaction %ith Sodium
Ta#le 8. #servations on 3art ''.B
Compound #servation
n-buty(
a(coho(
(0" :astest r4n+ turned 6hen sub2ected to (ighted
s!(inter
sec-buty(
a(coho(
(2" Moderate r4n+ *ormation o* co((oida( mi4ture+
turned ye((o6 6hen sub2ected to (ighted s!(inter
tert-buty(
a(coho(
(8" S(o6er r4n+ turned ye((o6 6hen sub2ected to
(ighted s!(inter
)heno( (9" S(o6est r4n+ 6hite so(id *ormed+ turned ye((o6
6hen sub2ected to (ighted s!(inter
Ta#le 9. Reactions 'nvolved in 3art ''.B
Reactions 'nvolved
(0"
C H
3
OH
+
Na
+
C H
3
O
-
Na
+
+
H
2 2
2 2
(2"
+
Na
+
C H
3
O
-
CH
3
Na
+
+
H
2 2
2 2
C H
3
OH
C H
3
(8"
+
Na
+
Na
+
+
H
2 2
2 2
OH
C H
3
C H
3
C H
3
O
-
C H
3
C H
3
C H
3
(9"
+
Na
+
Na
+
+
H
2
2 2
O
-
OH
.n terms o* the reaction 6ith sodium meta(+ it reacts 6ith
an a(coho( such that sodium reacts to the hydrogen o* the
hydro4y( grou! in order to (iberate hydrogen gas# &he rate o* this
reaction critica((y de!ends on the structure o* a(coho( 6ith
!rimary a(coho(s reacting the *astest *o((o6ed second and tertiary
a(coho(s#
:rom &ab(e 3 in7o(7ing the reactions o* the test
com!ounds+ 6e can see that n-buty( a(coho( reacted the *astest
6ith sodium+ *o((o6ed by sec-buty( a(coho(+ tert-buty( a(coho(+ and
!heno( as the s(o6est# 9e can obser7e their structures *rom
&ab(e 4 regarding their reactions+ n-buty( a(coho( reacted the
*astest because it is a !rimary a(coho(# Sec-buty( a(coho( reacted
the second *astest because it is a secondary a(coho(# &ert-buty(
a(coho( reacted the third *astest because it is a tertiary a(coho(#
Last(y+ !heno( reacted the s(o6est 6ith sodium meta( un(i5e the
other a(coho(s#
c. Reaction to Acetyl Chloride
Ta#le :. #servations on 3art ''.C
Compound #servation
,thy( a(coho( (0" C(ear (i?uid 63 bubb(es *ormed
)heno( (2" :oggy 6hite
Ta#le ;. Reactions 'nvolved on 3art ''.C
Reactions 'nvolved
(0"
C H
3
OH
1 ) a c e t y l c h l o r i d e
2 ) H
2
O
C H
3
O
CH
3
O
(2"
Experiment 03 Group No. 8 February 11. 2014 3 of
6
CHM143L Organic Chemistry 2 Laboratory
3rd Quarter SY 2013-2014 rou! "o# $% &he '(coho(ics
1 ) a c e t y l c h l o r i d e
2 ) H
2
O
OH
O C H
3
O
&he reaction o* a(coho( to acety( ch(oride demonstrate
the *ormation o* esters de!ending on the structure o* a(coho(s#
,thy( a(coho( and !heno( readi(y *ormed ethy( acetate and !heny(
acetate+ res!ecti7e(y by reacting 6ith acety( ch(oride because
ethy( a(coho( is a !rimary a(coho( 6hi(e !heno( is a secondary
a(coho(#
d. )ucas Test
Ta#le <. #servations on 3art ''.-
Compound #servation
n-buty( a(coho( (0" "o obser7ab(e e**ect
sec-buty( a(coho( (2" C(oudy 6hite so(ution
tert-buty( a(coho( (8" S(ight(y c(oudy 6hite so(ution/ *astest
reaction
Ta#le =. Reactions 'nvolved on 3art ''.-
Reactions 'nvolved
(0"
C H
3
OH
+
Cl H
ZnCl
3
n o r e a c t i o n
(2"
OH C H
3
CH
3
+
Cl H
ZnCl
3
Cl C H
3
CH
3
+
H
2
O
(8"
OH
C H
3
C H
3
C H
3
+
Cl H
ZnCl
3
+
H
2
O Cl
C H
3
C H
3
C H
3
&he Lucas reagent is used to react 6ith secondary and
tertiary a(coho(s to *orm a(5y( ch(oride# :rom &ab(es C and $+ it is
obser7ed that n-buty( a(coho( did not react 6ith the Lucas reagent
as com!ared to sec-buty( and tert-buty( a(coho(s# &his because o*
the structure o* the a(coho( being reacted 6ith# Sec-buty( and tert-
buty( a(coho(s !ossess secondary and tertiary a(coho(s
res!ecti7e(y+ 6hich stabi(i;es the carbocations *ormed# On the
other hand+ n-buty( a(coho( did not *orm a !roduct due to its
!rimary a(coho( structure# &he rate o* reaction is a(so a**ected
due to the structure o* the a(coho(# Obser7ed *rom &ab(e C+ tert-
buty( a(coho( reacts the *astest 6ith acety( ch(oride because it is a
tertiary a(coho( in 6hich *rom ho6 the e4!eriment 6as !er*ormed+
it reacted in (ess than a minute# Mean6hi(e+ sec-buty(
a(coho( reacted s(o6er because it is secondary a(coho(# &he
reaction 6as de7e(o!ed here on a s!an o* se7en minutes
a!!ro4imate(y#
e. xidation
Ta#le >. #servations on 3art ''.4
Compound Color of Solution dor of Solution
,thy( a(coho( 011 Ye((o6 to b(ue )(astic-ba((oon (i5e
.so!ro!y( a(coho(
021
Ye((o6 to dar5 b(ue 8ubbing a(coho(
tert-buty( a(coho( 031 Ye((o6 to orange Earnish
Ta#le 0?. Reactions 'nvolved on 3art ''.4
Reactions 'nvolved
(0"
C H
3
OH
1 ) d i l u t e H
2
S O

2 ) !
2
C r
2
O
"
C H
3 OH
O
(2"
C H
3
OH
C H
3
1 ) d i l u t e H
2
S O

2 ) !
2
C r
2
O
"
C H
3
CH
3
O
(8"
OH
C H
3
C H
3
C H
3
1 ) d i l u t e H
2
S O

2 ) !
2
C r
2
O
"
n o r e a c t i o n
'(coho(s can a(so be o4idi;ed de!ending a(so on its
structure# :rom &ab(e 10+ it can be obser7ed that ethy( a(coho(
6as o4idi;ed to an a(dehyde# &his a(dehyde can be *urther
o4idi;ed to carbo4y(ic acid de!ending on the reaction conditions#
)rimary a(coho(s are usua((y trans*ormed into these *unctiona(
grou! 6hen they undergo o4idation# 's *or iso!ro!y( a(coho(+ it
6as o4idi;ed+ ha7ing a *unctiona( grou! o* 5etone# -ased *rom
this+ secondary a(coho(s can be o4idi;ed to 5etones @ and that
6ou(d be it# Mean6hi(e *or tert-buty( a(coho(+ no reaction
occurred+ meaning that it 6as not o4idi;ed# &his is !rimari(y due
to the absence o* a hydrogen atom on the carbon direct(y
attached to the hydro4y( grou!# -ecause o* this+ no o4idation 6i((
ha!!en# &he o4idi;ing agent remo7es the hydrogen atom *rom
the hydro4y( grou! and remo7es a(so one *rom the carbon atom
direct(y attached to the hydro4y( grou!#
f. 'odoform Test
Ta#le 00. #servations on 3art ''.+
Experiment 03 Group No. 8 February 11. 2014 4 of
6
CHM143L Organic Chemistry 2 Laboratory
3rd Quarter SY 2013-2014 rou! "o# $% &he '(coho(ics
Compound #servation
,thy( a(coho( 011 )a(e ye((o6 to c(ear
.so!ro!y( a(coho( 021 )a(e ye((o6 to c(ear/ *ormation o*
ye((o6 !reci!itate
Ta#le 02. Reactions 'nvolved on 3art ''.+
Reactions 'nvolved
(0"
C H
3
OH
#
2
NaOH
O H
O
Na
(2"
C H
3
OH
C H
3
#
2
N a O H
C H
3
O
O
-
Na
+
+
CH#
3
&he .odo*orm test is used to identi*y the !resence o* a
CH3CH0OH1 grou! in a(coho(s# :rom &ab(e 12+ it is obser7ed that
on(y iso!ro!y( a(coho( bears the CH3CH0OH1 grou! because o* it
being a secondary a(coho(# .n addition to that+ it *ormed an
iodo*orm 0CH.31 in 6hich it is the ye((o6 !reci!itate described
*rom &ab(e 11# '(though ethy( a(coho( is a !rimary a(coho(+ it sti((
reacted 6ith iodine because ethy( a(coho( 6i(( be o4idi;ed into an
a(dehyde by the iodine grou! des!ite that no iodo*orm 6as
*ormed e7en though it is !er*ormed by iodo*orm reaction# '
negati7e resu(t 6i(( be (abe(ed on the ethy( a(coho( because no
secondary a(coho(s 6ere identi*ied#
g. Bromine *ater
Ta#le 08. #servations on 3art ''.6
Compound #servation
)heno( 011 C(oudy *ormation
-en;y( a(coho( 021 &urned into a ye((o6 mi4ture/
immiscib(e
Ta#le 09. Reactions 'nvolved on 3art ''.6
Reactions 'nvolved
(0"
OH
+
$r
2
OH
$r
+
$r H
(2"
OH
+
$r
2
OH
$r
OH
$r
+
&he bromine 6ater test is used to determine the
!resence o* acti7ated aromatic rings !articu(ar(y in !heno(s# :rom
the obser7ations tabu(ated on &ab(e 13+ !heno( *ormed a rather
c(oudy so(ution# &his indicates that it *ormed an a(most 6hite
!reci!itate+ indicating the !resence o* an acti7ated aromatic ring
due to the !resence o* the hydro4y( grou! that ma5es the
ben;ene ring more reacti7e than it 6ou(d be as com!ared to the
ben;y( a(coho(#
h. +eCl8 Test
Ta#le 0:. #servations on 3art ''.!
Compound #servation
)heno( 011 :rom ye((o6 orange to green so(ution
-en;y( a(coho( 021 "o change in co(or
Ta#le 0;. Reactions 'nvolved on 3art ''.!
Reactions 'nvolved
(0"
OH
+
%eCl
3
N
N
+
H
Cl H
+
%e&O'r(
3 3
3
(2"
OH
+
%eCl
3
N
3
3
n o r e a c t i o n
&he :eC(3 test is used in identi*ying eno( grou!s in an
organic com!ound# &his test distinguishes a(coho( *rom !heno(s
thorough(y# :rom the obser7ations and reactions in7o(7ed in
&ab(es 1= and 1D+ it is (isted that !heno( occurred a co(or change
*rom ye((o6 orange to green# ' green com!(e4+ in 6hich it is the
:eFO'rG3 com!ound+ sho6s a !ositi7e resu(t in the reaction+
ma5ing the !resence o* a !heno( 5no6n# On the other hand+
ben;y( a(coho( did not e4!erienced a co(or change# &his is due to
it being an a(coho( and not a !heno( because o* the e4tra carbon
bet6een the ben;ene ring and the hydro4y( grou!+ 6hich readi(y
distinguishes it *rom !heno(s# )yridine 6as uti(i;ed here in order
to !roduce more accurate resu(ts regarding this#
C,C).S',
Experiment 03 Group No. 8 February 11. 2014 5 of
6
CHM143L Organic Chemistry 2 Laboratory
3rd Quarter SY 2013-2014 rou! "o# $% &he '(coho(ics
&his e4!eriment aims to e4amine and di**erentiate the
!ro!erties o* a(coho(s !heno(s and to 7isua(i;e their characteristic
reactions# Se7era( tests 6ere uti(i;ed here in order to 5no6 the
di**erent !ro!erties !resent in a(coho(s and !heno(s+ 6hich they
are as *o((o6s% So(ubi(ity test+ 'cidity3-asicity+ 8eaction 6ith
Sodium+ 8eaction 6ith 'cety( Ch(oride+ Lucas test+ O4idation+
.odo*orm test+ -romine 9ater test+ and :erric Ch(oride test# &he
ob2ecti7es (isted here 6ere achie7ed#
So(ubi(ity beha7ior o* an a(coho( de!ends on the sur*ace
area o* its hydro!hobic region+ 6hich main(y contains continuous
carbon chains# &he cause o* its so(ubi(ity+ !articu(ar(y in 6ater+ is
due to its hydro!hi(ic region that consists o* the hydro4y( grou!#
'(coho(s and !heno(s are usua((y acidic because o* the
!resence o* a stab(e con2ugate base# .t is due to the resonance
stabi(ity and inducti7e e**ects caused by the o4ygen atom#
&he reaction o* an a(coho( 6ith sodium is one o* the
usua( acid-base reactions one might encounter in an organic
chemistry (aboratory# &he sodium meta( reacts to the hydrogen
attached to the hydro4y( grou! in order to (iberate hydrogen gas#
&his strong(y de!ends on the structure o* the a(coho(# )rimary
a(coho(s react the *astest to sodium+ 6ith secondary a(coho(s
being the ne4t+ then tertiary a(coho(s the s(o6est to react#
8eaction o* a(coho(s 6ith acety( ch(oride *orms esters
de!ending a(so on the structure o* the a(coho(# )rimary and
secondary usua((y *orm esters#
'(coho(s reacting 6ith Lucas reagent tend to *orm an
a(5y( ch(oride# &his is on(y to ha!!en i* the a(coho(s is secondary
or tertiary because they are the ones ca!ab(e o* !roducing a
carbocation o* greater stabi(ity as com!ared to !rimary a(coho(s#
&ertiary a(coho(s tend to react the *astest 6hen treated 6ith
Lucas reagent#
'(coho(s can be o4idi;ed de!ending a(so on the
structure o* the a(coho(s to be o4idi;ed# )rimary a(coho(s tend to
be o4idi;ed to a(dehyde and be *urther o4idi;ed to carbo4y(ic acid
de!ending on the conditions o* the reactions to be !er*ormed#
Secondary a(coho(s tend to o4idi;e on(y once into 5etones+
6hereas *or tertiary a(coho(s+ they do not undergo o4idation
because no hydrogen atom is !resent in the carbon direct(y
attached to the hydro4y( grou!#
&he .odo*orm test is used to identi*y the !resence o* a
secondary a(coho(s that ha7e a methy( grou! residing ne4t to the
carbon attached to the hydro4y( grou!# 9hen !er*ormed+ an
iodo*orm *orms in the *orm o* a ye((o6 !reci!itate that can
indicate a !ositi7e resu(t regarding the !articu(ar test#
-romine 6ater test is used to determine the
!resence o* acti7ated aromatic rings# )heno(s are usua((y
identi*ied because o* the !resence o* the o4ygen atom that
acti7ates the ring+ ma5ing it more reacti7e than usua(#
Last(y+ the *erric ch(oride test is used to detect the
!resence o* an eno( grou!# &his readi(y distinguishes a(coho(s
*rom !heno(s# ' !ositi7e test resu(t is indicated by a number o*
com!(e4es such as red+ green+ b(ue+ and !ur!(e com!(e4es#
-ecause o* some human sources o* error ha!!ened
during the !er*ormance o* the e4!eriment+ a !(ausib(e
recommendation than can be *ormu(ated *rom this is that to
*o((o6 thorough(y the !rocedures 6ritten on the manua( and i* the
instructor has some ad2ustments to the !rocedure+ ma5e sure to
ta5e note o* it and as5 ?uestions i* something is in mind#
R4+4R4,C4S
0 Baluyut& @.A. B -e Castro& C. rganic Chemistry )a#oratory
1anual for Chemical 4ngineering Students 3art 2.
2 Clein& -. R. rganic Chemistry& @ohn *iley B Sons& 'nc. Chapter
085 Alcohols and 3henols& (p.:;:-;20"
8 3arsons& A. +. (2?08". Ceynotes in rganic Chemistry& 2
nd
edition.
2?09.

Experiment 03 Group No. 8 February 11. 2014 6 of
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