Date: 19/01/2012

Instructor: Engr. Josephine A. Ng

Gochingco, Paolo Gioanni !.
E"peri#ent No. 1: !E$%ING P&IN% AND '&I$ING P&IN%( &) &*GANI+
+&!P&,ND(
A'(%*A+%
%he properties o- organic co#poun.s .epen. on their che#ical structures.
Inter#olecular -orces o- attraction a--ect ph/sical properties such as #elting
an. 0oiling point. %hrough the %ho#as 1ooer apparatus, the #elting point
o- 2 test co#poun.s 3as .eter#ine.. (alic/lic aci. e"hi0ite. the highest
#elting point 3hile naphthalene, the lo3est. %he stronger the inter#olecular
-orces o- attraction, the higher the #elting point. 'oiling point .eter#ination
3as .one on 4 .i--erent test co#poun.s using #icro #etho.. *esults sho3
that propanoic aci. an. n5he"ane ha. the highest an. lo3est 0oiling point
respectiel/. %he -or#er ha. the strongest inter#olecular -orce o- attraction
a#ong the test co#poun.s. %hus, there e"ists a .irect proportionalit/
0et3een inter#olecular -orces o- attraction in a co#poun. an. its #elting or
0oiling point. In a..ition, pure organic soli.s e"hi0it a sharp #elting point
range.
1
I. Intro.uction
!olecular structures proi.e an
un.erstan.ing o- the ph/sical an.
che#ical properties e"hi0ite. 0/
arious organic co#poun.s. %he/
account -or the -orces o- attraction
that 0in. #olecules o- a co#poun.
together. Inter#olecular -orces
inclu.e .ispersion -orces, .ipole5
.ipole interactions an. h/.rogen
0on.ing. Dispersion -orces, the
3ea6est a#ong the three, are
0rought a0out 0/ an instantaneous
or in.uce. polari7ation o-
#olecules. %he/ are also 6no3n as
an .er 8aals -orces or $on.on
-orces o- attraction. Dipole5.ipole
interactions e"ist a#ong polar
#olecules an. are stronger than
.ispersion -orces. A special 6in. o-
.ipole5.ipole -orce is h/.rogen
0on.ing 3hich is the strongest
inter#olecular -orce o- attraction.
%his is present a#ong #olecules
3ith h/.rogen 0on.e. to an
electronegatie ato# 9), & or N:.
Ph/sical properties such as 0oiling
point an. #elting point are largel/
in-luence. 0/ these inter#olecular
-orces. %he #elting point o- a soli.
co#poun. re-ers to the
te#perature in 3hich its soli. an.
li;ui. phases are in ./na#ic
e;uili0riu# 3ith each other at a
gien pressure. &n the other han.,
the 0oiling point o- a li;ui.
co#poun. is the te#perature at
3hich its apor pressure is e;ual to
the at#ospheric pressure. %hese
properties are o-ten use. in
characteri7ing or .eter#ining a
co#poun..
II. !etho.olog/
I. !elting Point
A. (tructural E--ect
a. Inter#olecular )orces o-
Attraction
%est +o#poun.s: )inel/ groun.
naphthalene, 0en7oic aci., salic/lic
aci., 0en7oin an. urea.
Proce.ure
1. Get capillar/ tu0es -ro# the
la0orator/ assistant an. seal one
en. o- each tu0e using heat. %he
instructor 3ill .e#onstrate ho3
this is .one. %hese tu0es 3ill sere
as the sa#ple hol.ers.
2. Get a s#all a#ount o- the soli.
sa#ple an. press it into the open
en. o- a capillar/ tu0e until enough
sa#ples are insi.e the tu0e. %ap
the close. en. o- the capillar/ tu0e
on the ta0le in or.er to #oe the
2
sa#ple to the 0otto#. I- the
sa#ple re#ains on the upper
portion o- the tu0e, .rop the
capillar/ tu0e insi.e a one #eter
glass tu0ing in 3hich one en. is
place. on the -loor. %he sa#ple
shoul. 0e at least <5= ## in
height an. #ust 0e tightl/ pac6e..
>. Place the capillar/ tu0e
containing the sa#ple insi.e the
sa#ple hol.er o- the %ho#as
1ooer Apparatus -or #elting point
.eter#ination.
?. (3itch on the apparatus. A.@ust
the heat an. turn on the stirrer.
*ecor. the te#peratures at 3hich
the co#poun. starts to li;ue-/ an.
at 3hich it has co#pletel/ li;ue-ie.
as the #elting5point range.
<. *epeat the a0oe proce.ures
until all the sa#ples 3ere teste..
Note: Allo3 the silicone -lui. to
cool .o3n -irst 0e-ore per-or#ing
another test.
0. Geo#etric Iso#ers
%est +o#poun.s: )inel/ groun.
#aleic aci. an. -u#aric aci.
Proce.ure: )ollo3 the sa#e
proce.ure as o- Part I.A.a.
'. E--ect o- Purit/ on !elting Point
*ange
%est +o#poun.s: )inel/ groun.
urea an. prepare. i#pure urea
Proce.ure: )ollo3 the proce.ure as
o- Part I.A.a.
II. 'oiling Point 0/
!icro !etho.
A. (tructural E--ect
a. Inter#olecular )orces o-
Attraction
%est +o#poun.s: n5'utanol, 25
'utanone, n51e"ane, n5Pentane,
Propanoic aci.
Proce.ure
1. )ill up the %hiele tu0e 3ith
gl/cerol up to the leel slightl/
a0oe its ar# an. asse#0le the
set5up.
2. Get a capillar/ tu0e -ro# the
la0orator/ assistant an. heat it at
the #i..le until the tu0e 0eco#es
co#pletel/ t3iste..
>. Place the capillar/ tu0e insi.e
the #icro test tu0e containing t3o
to three .rops o- the test
co#poun.s.
?. Place the #icro test tu0e
containing the sa#ple an. the
capillar/ si.e 0/ si.e 3ith the
ther#o#eter. ,se a 25## 3i.e
ru00er tu0ing to hol. the capillar/
tu0e.
<. I##erse the ther#o#eter in
the gl/cerol 90ath li;ui.: ensuring
>
that the ru00er tu0ing is not
i##erse. in the li;ui..
=. 1eat the oil 0ath rapi.l/ until a
-lo3 o- 0u00les co#es out o- the
capillar/ tu0e.
4. *e#oe the -la#e an. allo3 the
oil to cool .o3n. As the
te#perature .rops, the 0u00ling
3ill slo3l/ cease an. the li;ui. 3ill
start to enter the capillar/ tu0e.
*ecor. this te#perature as the
0oiling point o- the test co#poun..
2. %o o0tain the 0oiling point range
o- the test co#poun., reheat the
oil slo3l/ an. note the te#perature
3hen the li;ui. co#es out o- the
capillar/ tu0e. %he te#perature
preiousl/ recor.e. an. this
current te#perature is the 0oiling
point range.
9. *epeat the a0oe proce.ure
until all the sa#ples are teste..
Note: Allo3 the gl/cerol to cool
.o3n to roo# te#perature 0e-ore
reusing it.
0. 'ranching
%est +o#poun.s: n50ut/l alcohol,
sec50ut/l alcohol an. tert50ut/l
alcohol
Proce.ure: )ollo3 the sa#e
proce.ure as o- Part II.A.a.
III. E"peri#ental *esults
I. !elting Point
A. (tructural E--ect
a. Inter#olecular )orces o-
Attraction
+o#poun. %1 A+ %2 A+
0en7oic aci. 122.2 12=.0
0en7oin 129.0 1>?.2
naphthalene 21.4 2=.9
salic/lic aci. 1<2.2 1=1.<
urea 1>?.0 1>=.0
0. Geo#etric Iso#ers/(u0stituent
+o#poun. %1 A+ %2 A+
#aleic aci. 1>9.0 1?0.2
-u#aric aci. 14?.0 14<.0
'. E--ect o- Purit/ on !elting Point
*ange
+o#poun. %1 A+ %2 A+
pure urea 1>?.0 1>=.0
i#pure urea 102.2 1>2.?
II. 'oiling Point 0/
!icro !etho.
A. (tructural E--ect
a. Inter#olecular )orces o-
Attraction
+o#poun. %1 A+ %2 A+
n50utanol 112 120
250utanone 20 2?
n5heptane 110 102
propanoic aci. 1>2 1>2
n5he"ane == =2
?
0. 'ranching
+o#poun. %1 A+ %2 A+
n50ut/l alcohol 112 120
sec50ut/l alcohol 92 102
tert50ut/l alcohol 2? 20
IB. Interpretation
In #elting point .eter#ination,
salic/lic aci. e"hi0ite. the highest
#elting point. It is -ollo3e., in
or.er o- .ecreasing #agnitu.e, 0/
urea, 0en7oin, 0en7oic aci. an.
naphthalene. %he .i--erences in
#elting point can 0e correlate.
3ith the inter#olecular -orces o-
attraction present in each
co#poun.. Naphthalene, haing
the relatiel/ 3ea6 .ispersion
-orces a#ong its #olecules, has
the lo3est #elting point. 'en7oic
aci., on the other han., is capa0le
o- h/.rogen 0on.ing through the
h/.rogen in its car0o"/lic group.
%his #a/ not 0e as strong as
h/.rogen 0on.ing in urea 3hich is
has 2 a#ine groups, each capa0le
o- h/.rogen 0on.ing. 'oth 0en7oin
an. salic/lic aci. o3e their high
#elting point to intra#olecular
h/.rogen 0on.ing. 8hereas
0en7oin has 1 h/.ro"/l group -or
h/.rogen 0on.ing, salic/lic aci.
has 2 h/.ro"/l groups. %here-ore,
salic/lic aci. has a higher #elting
point than 0en7oin.
)u#aric aci. .ispla/e. a higher
#elting point than #aleic aci..
'oth co#poun.s are
stereoiso#ers. In particular,
-u#aric aci. is a trans5iso#er 3hile
#aleic aci. is a cis5iso#er. In
-u#aric aci., the t3o car0o"/lic
groups lie on opposite si.es o- the
.ou0le 0on. in the co#poun.. %his
causes 0etter #olecular pac6ing
an. thus, stronger inter#olecular
-orces. 1ence, it has a higher
#elting point.
Pure soli. urea has a sharper
#elting point, that is, it #elts oer
a narro3 range o- te#perature
co#pare. 3ith i#pure urea.
I#purities cause. a lo3er #elting
point an. generate. a 3i.er
#elting te#perature range. 8hen
#elting occurs, soli. particles
ac;uire su--icient ther#al energ/ to
oerco#e cr/stalline -orces that
hol. the# together an. 0eco#e
li;ui.. !olecules o- pure urea, .ue
to 0eing ho#ogeneous, #elt
in.epen.entl/ an. al#ost at the
sa#e te#perature. %his e"plains
the sharper #elting te#perature
range. In contrast, i#pure urea is
co#prise. o- heterogeneous
#olecules 3hich .i--er in #elting
point, generating a 3i.er #elting
te#perature range.
<
A#ong the polar organic
co#poun.s, propanoic aci. has the
highest 0oiling point an. 25
0utanone, the lo3est, 3hile n5
0utanol is inter#e.iate. 25
0utanone is capa0le o- .ipole5
.ipole interactions 3hich, ho3eer,
are not as strong as h/.rogen5
0on.ing present in n50utanol an.
propanoic aci.. N50utanol is
capa0le o- onl/ one inter#olecular
h/.rogen 0on. 3hereas propanoic
aci. can hae t3o inter#olecular
h/.rogen 0on.s. %his is the reason
3h/ propanoic aci. has a higher
0oiling point than n50utanol.
'et3een n5heptane an. n5he"ane,
3hich are 0oth non5polar organic
co#poun.s, n5heptane has a
higher 0oiling point. %his can 0e
attri0ute. to the stronger an .er
8aals or $on.on .ispersion -orces
present in the heaier heptane.
$engthening a straight car0on
chain, thus, has the e--ect o-
increasing inter#olecular -orces o-
attraction an. 0oiling point.
+ontrasting polar an. non5polar
organic co#poun.s o- co#para0le
#olecular 3eight, the -or#er group
0oils at a higher te#perature.
Principall/, this is 0ecause .ipole5
.ipole -orces are stronger than
.ispersion -orces.
N50ut/l alcohol has a higher 0oiling
point than sec50ut/l alcohol. An.
sec50ut/l alcohol has a higher
0oiling point than tert50ut/l
alcohol. %his .e#onstrates that
0ranche. #olecules hae a lo3er
0oiling point than linear #olecules.
%he #ore e"tensie 0ranching is,
the lo3er the 0oiling point.
'ranching re.uces the area o-
contact 0et3een #olecules. 1ence,
less or 3ea6er inter#olecular
-orces o- attraction e"ist in the
co#poun..
B. +onclusion
'ase. on the e"peri#ental results,
it can 0e conclu.e. that a
co#poun. 3ith stronger
inter#olecular -orces has a higher
#elting or 0oiling point than a
co#poun. haing 3ea6er
inter#olecular -orces. )or
geo#etric iso#ers, the trans5
iso#er generall/ e"hi0its a higher
#elting point than its cis5iso#er.
(traight5chaine. organic
co#poun.s sho3 a higher 0oiling
point that those 3ith 0ranche.
chains.
%hrough #elting point
.eter#ination, the purit/ o- an
organic co#poun. can 0e chec6e..
A pure co#poun. .ispla/s a
=
narro3 te#perature range -or its
#elting point.
BI. *e-erences
'alu/ot, J. C De +astro, D. 9n...:.
&rganic +he#istr/ $a0orator/
!anual -or +he#ical Engineering
(tu.ents Part I. Intra#uros:
!apua Institute o- %echnolog/.
$i#5(/lianco, +. 9199?:. Principles
o- &rganic +he#istr/. 92
th
e.ition:.
Eue7on +it/: Auru# %echnical
'oo6s.

!orrison, *. C 'o/., *. 91924:.
&rganic +he#istr/. 9<
th
e.ition:.
!assachusetts: All/n an. 'acon,
Inc.
BII. Gui.e Euestions
1. *an6 the -ollo3ing co#poun.s
in .ecreasing #elting point:
0en7oic aci., 0en7oin,
naphthalene, salic/lic aci. an.
urea. Justi-/ /our ran6 0/ citing
the inter#olecular -orces o-
attraction present in the particular
co#poun..
In or.er o- .ecreasing #elting
point, the arrange#ent is as
-ollo3s: salic/lic aci., urea,
0en7oin, 0en7oic aci. an.
naphthalene. Naphthalene has
.ipole5.ipole -orces. 'en7oic aci.
an. urea are capa0le o-
inter#olecular h/.rogen 0on.ing.
'en7oin an. salic/lic aci. hae
intra#olecular h/.rogen 0on.ing.
2. 1o3 .oes #olecular geo#etr/
a--ect the #elting point o- an
organic co#poun.F
A trans5iso#er o- an organic
co#poun. has a higher #elting
point that its cis5iso#er.
>. 1o3 .o i#purities a--ect the
#elting point o- an organic
co#poun.F
I#purities cause a 3i.er range -or
the #elting point o- an organic
co#poun..
?. In general, 3hat are the -actors
that a--ect the #elting point o- an
organic co#poun.F 8hat are the
e--ectsF
!olecular -orces o- attraction,
#olecular geo#etr/ an. purit/
a--ect the #elting point o- an
organic co#poun.. (trong
inter#olecular or intra#olecular
-orces result to a high #elting
point. %rans5iso#ers #elt at higher
te#perature than cis5iso#ers. Pure
organic co#poun.s hae a sharp
#elting point range.
<. +onsi.er the 0oiling point o- n5
0utanol, 250utanone, n5pentane
an. propanoic aci.. 1o3 .oes
4
polarit/ a--ect the 0oiling point o-
organic co#poun.sF
In or.er o- increasing 0oiling point,
the arrange#ent is as -ollo3s: n5
pentane, 250utanone, n50utanol
an. propanoic aci.. %he #ore polar
an organic li;ui. co#poun. is, the
higher its 0oiling point.
=. +o#pare the #elting points o-
n5heptane an. n5he"ane. 8hich
has the higher 0oiling pointF Justi-/
/our ans3er.
N5heptane has a higher #elting
point than n5he"ane .ue to its
higher #olecular 3eight or
stronger .ispersion -orces.
4. +o#pare the 0oiling points o- n5
0ut/l alcohol, sec50ut/l alcohol,
an. tert50ut/l alcohol. 8hat #a6es
the .i--erenceF
In or.er o- .ecreasing 0oiling
point, the arrange#ent is as
-ollo3s: n50ut/l alcohol, sec50ut/l
alcohol, an. tert50ut/l alcohol.
'ranche. #olecules 0oil at a lo3er
te#perature than straight5chaine.
#olecules. 'ranching results in
#ore co#pact #olecules an.
hence, less area o- contact
0et3een the#. +onse;uentiall/,
3ea6er inter#olecular -orces are
present.
2. In general, 3hat are the -actors
that a--ect the 0oiling point o-
organic co#poun.sF 8hat are the
e--ects o- each -actorF
Polarit/ an. #olecular 0ranching
a--ect the 0oiling point o- organic
co#poun.s. %he #ore polar a
co#poun. is, the higher the 0oiling
point. %he #ore e"tensie the
#olecular 0ranching, the lo3er the
0oiling point.
2