CHM142L Organic Chemistry 1 Laboratory 2nd Quarter SY 2013-2014

Miranda, Marilyn1, Teodoro, Nowell Neill D2

1

ro!essor" Schoo# o! Chemica# $ngineering" Chemistry and %iotechno#ogy" Ma&ua 'nstitute o! (echno#ogy) 2Student" CHM142L %21" Schoo# o! Chemica# $ngineering" Chemistry and %iotechno#ogy" Ma&ua 'nstitute o! (echno#ogy

ABSTRACT
Boiling points and melting points are some of the physical characteristics of a substance or compound. Both properties define the changes of a substance from one state to another state. Melting point notes the temperature where the solid and liquid phase is at equilibrium, while the boiling point is the temperature where the apour pressure is equal to the pressure of the atmosphere. Through this e!periment, the principles behind the melting point and boiling point of compound will be gi en a deeper loo". #sing specific apparatuses li"e Thomas $oo er Apparatus and Thiele Tube with glycol, the boiling point and melting points of organic compounds will be determined. %rom that, the factors that affect the melting points and boiling points of a substance will also be studied. The determination of such characteristics will also e!plain how the ariation of each organic compound differs to any other compound. Moreo er, the relationship of the intermolecular forces, isomers, branching and purity to the melting point and boiling points will be associated through this e!periment. &ith the gathered data, each compound is compared to each other to erify the effecti eness of the factors that influence such characteristics. %rom the results, it is certain the factors li"e intermolecular force, branching, purity and molecular weight greatly influence the melting point and boiling point range of an organic compound. Keywords: boiling point, melting point, intermolecular forces, branching, purity, molecular weight

'(TR)*#CT')( Me#ting &oints and boi#ing &oints are so#e#y considered as

the physical characteristics or properties of a substance. These characteristics define the changes of a substance from one state to another state. For the melting point, a solid substance is converted into liquid state wherein the it is in contact with heat. In contrast, boiling points define the conversion of liquid to gas or vapor when in contact with heat. Also, Melting points and boiling points varies depending on the substance and its intermolecular force.

&oint is de!ined as the tem&erature at a s&eci!ic &ressure at ,hich the so#id and #i.uid &hases are in e.ui#ibrium ,ith each other* /Castro" %a#uyot0 1n energy or heat must be in contact ,ith the com&ound thereby brea2ing the intermo#ecu#ar !orce o! a so#id com&ound ,hich ,i## ma2e it into the !reer #i.uid state* 3n#i2e me#ting &oint" boi#ing &oint is used to define
the alteration of a liquid organic compound s physical property to come up with a gas state. !hen the liquid compound is heated, it will reach a certain temperature where vapor pressure is large enough to form bubbles inside the system. The alteration of the boiling points is done in such a way that the factors are related to properties of the molecules. "ne factor is its molecular weight# compound with higher molecular weight will result to higher boiling point. "ther factors include the strength of the intermolecular force and polarity of the compound.

(he structura# theory suggests that the &ro&erties o! an organic com&ound are in!#uenced by the chemica# structure o! the com&ound* (heoretica##y" these structures act in
accordance with chemical and physical property of a compound. Therefore, the melting points and boiling points can be easily measured by altering the physical property of an object.

Com&ounds that are in crysta##ine so#id !orm con+ey the de!inition o! a ,e##-arranged and organi-ed structure* %y a#tering the &hysica# &ro&erty o! an organic so#id com&ound" or any other so#id com&ound" ,i## resu#t to me#ting* Me#ting

%y de!inition" the me#ting &oints and boi#ing &oints ,i## +ary de&ending on the com&ound and the !actors that ,i## a!!ect and in!#uence the a#teration o! an ob4ect*

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(here!ore" the &ur&ose the e5&eriment is to determine the me#ting &oint and boi#ing &oint o! certain substances such as na&htha#ene" urea" n-%utano#" 2-%utanone etc* (he determination o! the me#ting and boi#ing &oint o! a com&ound ,i## a#so de!ine the in!#uence o! the intermo#ecu#ar !orce &resent in a com&ound* (he researchers or grou& tries to a#ter the &hysica# &ro&erty by heating the substance in a g#ycero# that ,i## resu#t to its me#ting &oint and boi#ing &oint* MAT+R'A,S A(* M+T$)*S (he e5&eriment is di+ided into t,o &arts* (he !irst &art ,i## determine the me#ting &oint o! certain com&ounds #i2e na&htha#ene" ben-oic acid" sa#icy#ic acid ben-oin" &ure and im&ure urea" ma#eic acid" and !umaric acid* (his &art ,as di+ided a#so into t,o) name#y the e!!ect o! structura# and &urity o! a com&ound in its me#ting &oint* 6or the e!!ect o! &urity" the &ure and im&ure urea ,as tested* (he rest ,as tested as an e!!ect o! structura# theory in me#ting &oint* Ca&i##ary tubes sea#ed on one end" by heating" ,ere used to contain the sam&#es needed* 6rom that" each sam&#e re.uires di!!erent ca&i##ary tube* (he sam&#es ,ere &#aced in the tube in about 1 cm* (he sam&#e ,as then &#aced to the (homas Hoo+er 1&&aratus to determine its me#ting &oint* (he heat ,as changed de&ending on ho, the substances ,i## react or me#t* 6or this" t,o tem&erature mere measured* One tem&erature indicated the start o! the me#ting o! the com&ound* (he #atter ,as noted ,hen the com&ound is com&#ete#y me#ted* (he acce&ted +a#ue o! me#ting &oints ,as gi+en by the &ro!essor" Mari#yn Miranda* Same &rocedures are done ,ith the &urity &art* (he &ure urea is the same ,ith the urea used in the structura# &art* 6or the #atter &art o! the e5&eriment" boi#ing &oints ,i## be determined by using g#ycero# and heating it to a hot &#ate* Li2e the !irst &art" this ,i## a#so di+ided into t,o &arts) name#y the structura# e!!ect and the branching* (he reagents !or the structura# e!!ect &art are n-%utano#" 2%utanone" n-He5ane" n- entone and ro&anoic acid* (hese reagents ,ere tested to so#e#y determine its boi#ing &oint* 1 (hie#e tube ,as !i#ed u& ,ith g#ycero# unti# it reaches to the #e+e# ,here it is s#ight#y abo+e the arm o! the ho#der* (hen" the (hie#e tube ,as connected to an iron stand to stabi#i-e the set-u&* 3n#i2e the !irst &art" this &art used a hot &#ate to heat the reagents and the g#ycero#* 3&on com&#eting this" the reagents are &#aced in the micro test tube ,ith a ca&i##ary tube that is sea#ed on one end" by heating* (he reagents ,ere re.uired to ha+e one micro test tube and ca&i##ary tube each* (,o to three dro&s o! the reagent ,ere &#aced in the micro test tube then it ,as grou&ed ,ith a

thermometer using rubber tubing* (he thermometer and micro test tube ,ere he#d together by a cor2* 't ,as then he#d by an iron ho#der that is connected to an iron stand* (he thermometer and test tube ,as immersed in the g#ycero# ,ithout di&&ing the rubber tubing into the so#ution* 6rom that" the g#ycero# ,as heated unti# bubb#ed had a&&eared to the ca&i##ary tube* (he heat ,as then turned o!! and #et the g#ycero# coo#ed do,n* (he tem&erature ,as measured as it begins to come u& the ca&i##ary tube and noted as (1* (he set-u& ,as the heated" but this s#o,#y" unti# such time that the sam&#e had come out the ca&i##ary tube* (he tem&erature ,as again measured and noted as (2* 1gain" the acce&ted boi#ing &oints ,ere gi+en by the &ro!essor*

6igure 17 Set-u& !or determining the me#ting &oint

/Source7 8oog#e 'mages0

R+S#,TS Table -.- *etermination of Melting .oint/ 'ntermolecular %orces of Attraction

Compound %en-oic 1cid %en-oin <a&htha#ene Sa#icy#ic 1cid 3rea

T- 01C2 104 12: :0 193 120

T3 01C2 119 1:; :4 1=0 130

Melting .t. 122 134 :1*9 19;*9 133*9

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Table -.3 *etermination of Melting .oint/ 4eometric 'somers or Substituents

n-%uty# 1#coho# Sec-%uty# 1#coho# (ert-%uty# 1#coho#

=2 :0 =2

=4 := >2

11> ;; :2

Compound Ma#eic 1cid 6uramic 1cid

T- 01C2 ;3 2=>

T3 01C2 11> 2:>

Melting .t. 13:

Table -.5 *etermination of Melting .oint/ +ffect of 'mpurity in Melting .oint Range

6or (ab#e 1*1" 1*2 and 1*3" di!!erent so#id com&ounds ,ere tested to determine the me#ting &oint* 6or (ab#e 1*1" na&htha#ene has the #o,est me#ting &oint and sa#icy#ic acid as the highest* (ab#e 1*2 sho,ed that !uramic acid hsas higher me#ting &oint than that o! ma#eic acid* (ab#e 1*3 then sho,ed that &ure urea has higher boi#ing &oint* Some o! so#id com&ounds" ben-oic acid and ma#eic acid" don?t accurate#y con!orm to the acce&ted +a#ue o! its me#ting &oint* (ab#e 1*4 and 1*9 sho,ed the di!!erent boi#ing &oints o! #i.uid com&ounds tested during the e5&eriment* Most o! the gathered data doesn?t con!orm to the acce&ted +a#ue o! boi#ing &oint name#y7 n-%utano#" ro&anoic 1cid and n-%uty# 1#coho#*

Compound ure 3rea 'm&ure 3rea

T- 01C2 120 ;9

T3 01C2 130 110

Melting .t. 133*9

Table -.6 *etermination of Boiling .oint/ 'ntermolecular %orces of Attraction

Compound n-%utano# 2-%utanone n- entane ro&anoic 1cid n-He5ane

T- 01C2 =2 >: :; >9 =1

T3 01C2 =4 ;0 >= >> :0

Boiling .t. 11> >;*= ;:*4 141 =;

*'SC#SS')( %ased on the gathered data" the me#ting &oints o! the so#id reagents ,ere com&#ete#y identi!ied* 6or (ab#e 1*1" the me#ting &oints are arranged in decreasing order name#y7 sa#icy#ic acid" urea" ben-oin" ben-oic acid and na&htha#ene* 1s obser+ed" na&htha#ene has the #o,est me#ting &oint and sa#icy#ic acid has the highest* (he reason behind this +ariation is because o! the intermo#ecu#ar !orces ho#ding the mo#ecu#es o! the com&ound together* (he intermo#ecu#ar !orce &resent in na&htha#ene is the London or dis&ersion !orce ,hich is a ,ea2 !orce thereby #o,ering the me#ting &oint o! the com&ound* (he other !our com&ounds" Sa#icy#ic acid" %en-oin" %en-oic 1cid and urea ha+e higher me#ting &oints because o! their stronger intermo#ecu#ar !orce* 1side !rom the dis&ersion !orce" these !our com&ounds a#so con!orm to di&o#e-di&o#e !orce ,hich gi+es the com&ound a characteristic o! ha+ing a higher me#ting &oint* 1#so" i! you #oo2 c#ose#y to the com&onent o! these com&ounds" Hydrogen bonding is a#so &resent in each com&ound ,hich

Table -.7 *etermination of Boiling .oint/ Branching

Compound

T- 01C2

T3 01C2

Boiling .t.

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ma2es the other !our higher in me#ting &oint range* (he Hydrogen in urea is bonded to nitrogen and the hydrogen o! the three com&ounds" %en-oic 1cid" %en-oin and Sa#icy#ic 1cid" is bonded to o5ygen" there!ore ma2ing their me#ting &oints higher than any other organic com&ound* (ab#e 1*1 discusses ho, these intermo#ecu#ar !orces a!!ect the me#ting &oint o! an organic com&ound* (ab#e 1*2 sho,s that !uramic acid ha+e higher me#ting &oint com&ared to that o! ma#eic acid* 1#though they ha+e simi#ar mo#ecu#ar !ormu#a" they resu#ted to a +aried range o! me#ting &oint* (he reason behind is that Ma#eic 1cid is more stabi#i-e than 6uramic 1cid" thereby ma2ing it hard to brea2" causing the e#e+ation o! me#ting &oint* (he mo#ecu#ar geometries a#so o! these t,o isomers a!!ect their me#ting &oints* (he more symmetrica# the com&ound is" the higher the me#ting &oint* (ab#e 1*3 discusses the e!!ect o! im&urity in me#ting &oints* 't can be conc#uded that the &ure urea has higher me#ting &oint than that o! the im&ure* Com&ounds that ha+e an organi-ed crysta# #attice ,i## resu#t to higher me#ting &oint* 'n the case o! these t,o" the #attice o! im&ure urea is disru&ted by the im&urities ma2ing the me#ting &oint #o,er* 6or the &ure urea" it has organi-ed crysta# #attice there!ore ma2ing its me#ting &oint higher* 't can be stated that the intermo#ecu#ar !orce" mo#ecu#ar geometry and &urity o! a com&ound can a!!ect its me#ting &oint* Stronger intermo#ecu#ar !orce" more symmetrica# mo#ecu#ar geometry and more organi-ed crysta# #attice ,i## a#,ays resu#t to higher me#ting &oint* (he second &art" in contrast ,ith !irst &art" discusses the boi#ing &oints o! the #i.uid reagents* Some o! the com&ound does not accurate#y con!orm to the acce&ted +a#ue" maybe" because o! im&ro&er hand#ing o! the a&&aratus and reagents* 1nother reason is that" the reagent must be e5&osed too #ong to the atmos&here ma2ing some im&urities goes to the reagent* Considering the acce&ted +a#ues !or (ab#e 1*4" &ro&anoic acid has the highest boi#ing &oint and n-He5ane has the #o,est* Li2e na&htha#ene" n-He5ane has a dis&ersion !orce acting on its mo#ecu#es* 1gain" that is the reason ,hy it has #o,er boi#ing &oints is its intermo#ecu#ar !orce* 2-%utanone has doub#e bond ,ith o5ygen ,herein it is more di!!icu#t to brea2 causing it to e#e+ate the boi#ing &oint* <-He5ane" on the other hand" has a #onger carbon-chain &resent in the com&ound there!ore ma2ing the boi#ing &oint higher*

ro&anoic acid and n-%utano# because o! its Hydrogen %onding" hydrogen connected to o5ygen* %ased on its chemica# structures" n-%uty# a#coho# has the #o,est branching ,hi#e tert-%uty# a#coho# has the highest branching* 1s obser+ed in (ab#e 1*9" n-%uty# has the highest boi#ing &oint and tert-%uty# a#coho# is the #o,est* Since" the strength o! intermo#ecu#ar !orce is &ro&ortiona# to the si-e o! the mo#ecu#e) ,e can say the branching" in regards ,ith the sur!ace" ,i## reduce the boi#ing &oint C)(C,#S')(S A(* R+C)MM+(*AT')(S (hroughout the e5&eriment" the &rinci&#es behind the boi#ing &oint and me#ting &oint o! an organic com&ound ,as thorough#y studied* (he di!!erent !actors a!!ecting the &hysica# characteristics" s&eci!ica##y me#ting and boi#ing &oint" o! an organic com&ound ,as gi+en a dee&er #oo2* (he me#ting &oint o! a substance is the tem&erature in ,hich the so#id is con+erted to #i.uid* (he a#teration o! so#id &hase and #i.uid &hase is at e.ui#ibrium* (hrough this e5&eriment" ,e can conc#ude that the intermo#ecu#ar !orce &resent in an organic com&ound ,i## most #i2e#y a!!ect the range o! me#ting &oint* (here!ore" substances ,ith a hydrogen bonding and di&o#e-di&o#e !orce ,i## ha+e the higher me#ting &oints* 'n contrast" dis&ersion !orces in a com&ound ,i## #ead to #o,er me#ting &oints* Other than the intermo#ecu#ar !orce o! a com&ound" the mo#ecu#ar geometry o! an ob4ect ,i## a#so in!#uence its me#ting &oint* 1 symmetrica# arrangement ,i## #ead to a higher me#ting &oint* 6or the isomers" the one ,ith the stabi#i-e !orm ,i## ha+e higher me#ting &oint too* 1#so" ,e can conc#ude that im&ure substances ha+e #o,er me#ting &oints than that o! &ure substances* (his is by the reason that im&urities disru&t the crysta# #attice o! a com&ound thereby #o,ering its me#ting &oint** %oi#ing &oint" on the other hand" is de!ined as the tem&erature ,herein the +a&our &ressure is e.ua# to the &ressure on the atmos&here* Li2e me#ting &oint" there are certain !actors that a!!ect the range o! boi#ing &oint* One !actor is" again" the intermo#ecu#ar !orce o! the com&ound* (he stronger the intermo#ecu#ar !orce &resents in a com&ound" the higher the boi#ing &oint* So Hydrogen bonding and di&o#e !orces ,i## a#,ays ha+e a higher boi#ing &oint than that o! dis&ersion !orces* 1#so" the other !actor is the branching o! the com&ound* (he branching causes a reduction ,ith regards to the sur!ace area thereby #o,ering the boi#ing &oint*

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(hese !actors must be ta2en into consideration to understand the &rinci&#es behind the me#ting and boi#ing &oint o! an organic com&ound* 'n order to a+oid any errors in determining the boi#ing and me#ting &oint" ma2e sure that the reagents are not e5&ose too #ong to the atmos&here* 1#so" ma2e sure that the set-u& or a&&aratus is ,or2ing or &ro&er#y set-u&* R+%+R+(C+S @1A %a#uyot" B* Y*" Castro" C*" Organic Chemistry Laboratory Manua# !or Chemica# $ngineering Students @2A Dhitten C* D*" Ea+is F* $*" ec2 L*" Stan#ey 8* 8*" Chemitstry ;th edition /20100 %e#mont" Ca#i!ornia 3S1

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