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Experiment # 9: Synthesis of Organic Compounds Pancho, Thatcher; Sadudaqui , !

erome "roup #9: Chemistry #$%$, &'C(, &r% 'aro d 'enrison Chiu Septem)er 9, *+$+ I. Abstract

,ti i-ation of organic compounds is e.ident in man/s dai y acti.ities, as these ser.e for a .ariety of purposes, from industria to home usage% 0s such, microsca e production of certain organic compounds is done for scientific inquiry% 1n this experiment, different chemica reactions yie ded to the syntheses of three organic compounds: $2pheny a-o2*2naphtho 3Sudan 145, soap and acety sa icy ic acid 3aspirin5% 0-oti-ation and coup ing reactions 6ith high y acti.ated aromatic compounds 6ere in.o .ed in synthesi-ing dye% Saponification of hydrogenated softener and sodium hydroxide formed the soap 6hi e esterification of sa icy ic acid yie ded the aspirin% Physica and chemica tests 6ere done on the products to determine purity and other properties% 1t 6as o)ser.ed that the synthesi-ed organic compounds exhi)it unique properties: the dye 6as intense y co ored, the soap 6as s ippery, and aspirin 6as granu ated and crysta 2 i7e% 1t 6as a so found that certain requirements in synthesi-ing organic compounds, such as temperature and a 7a inity, must )e met in order to successfu y yie d the products% II. III. Keywords: $2pheny a-o2*2naphtho , soap, acety sa icy ic acid, dia-oti-ation, esterification, saponification Introduction The groups 6ere di.ided into three% =ots 6ere dra6n to determine 6hat particu ar synthesis a group 6i )e performing% A. Synthesis of Dye (1-Phenylazo-2-naphthol) 1n a >+2m= )ea7er, +%9 m= of ani ine, $%? m= of 6ater, and *%$m= of concentrated hydroch oric acid 6ere com)ined% The contents 6ere then coo ed to a +2> @C and then $ g of ice 6as added% So ution of sodium nitrate 6as dropped unti the reaction mixture contained excess acid% 1t 6as then tested for excess nitrous acid )y spotting a drop on the starch2iodide paper% The temperature of the reaction mixture 6as 7ept )e o6 > @C% To prepare the a 7a ine so ution, $%? g of A2naphtho 6as disso .ed in # m= of a #& aqueous sodium hydroxide% 1t 6as coo ed then to > @C and pheny dia-oniun ch oride 6as added 6ith stirring% The reaction 6as a o6ed to stand for $> minutes at +2> @C% The product 6as co ected )y gra.ity fi tration on f uted fi ter paper 6ashed 6ith se.era portions of co d 6ater% The product 6as 6eighed 3ho6e.er, the percent yie d 6as not ca cu ated anymore5% 1n testing the products for physica properties, the appearance, co or, texture and odor of the product 6ere noted% 1ts me ting point 6as a so determined% Bor chemica tests, a pinch of the product 6as disso .ed in > m= of disti ed 6ater% Three drops of this so ution 6ere added to a test tu)e 6ith * m= of +%$ & CaO'% The same procedure 6as repeated using +%$ & 'C , C'?O', and C'#COO'% B. Synthesis of Soap

Of the estimated 8 mi ion organic compounds 7no6n, most ha.e )een made )y synthesis rather than iso ated from nature% 9ith this information, synthesis of organic compounds has de.e oped into one of the most important fie ds in chemistry% Organic synthesis is a specia )ranch of chemica synthesis concerned 6ith the construction of organic compounds )y means of organic reactions% :easons for synthesi-ing compounds inc ude proof of structure of a natura compound )y com)ining simp er mo ecu es and faci itating product formation through specific organic reactions and to prepare specific compounds to study reaction mechanisms or )io ogica mechanisms% 1n preparing a 7no6n compound, a pu) ished setup appropriate for the 6or7 is fo o6ed% The choice may .ary according to the a.ai a) e starting materia s, a)oratory equipments, chemist;s experience and the experimenta ad.antage% The simp est synthesis of a mo ecu e is one in 6hich the target mo ecu e can )e o)tained )y su)mitting a readi y a.ai a) e starting materia to a sing e reaction that con.erts it to the desired target mo ecu e% Organic synthesis, then, p ays an important ro e )y a o6ing for the creation of specific mo ecu es for scientific and techno ogica in.estigations% The o)<ecti.es of this experiment are: $5 to app y certain chemica reactions earned in the ecture c ass and *5 to study and i ustrate se.era properties of organic synthesis% This experiment 6i he p students in disco.ering the 6onders of organic reactions and ser.e as a temp ate for future scientific purposes% IV. Experimental Chem #$%$, Synthesis of Organic Compounds

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*%> grams of CaO' 6as disso .ed in >2m= 6ater and $+ m= of 9>D C'#COO'% The so ution 6as then added to > grams of hydrogenated shortening in a $>+2m= )ea7er% The )ea7er 6as co.ered 6ith a 6atch g ass and heated in a 6ater )ath that 6as pre.ious y prepared% >+D of a coho 6as added 6ith constant stirring to maintain the consistency of the so ution/s .o ume% 0 c ear homogenous so ution 6as then o)tained and a the me ted fat 6as comp ete y disso .ed% The soap 6as di uted 6ith $> m= 6ater and 6as poured in a )rine so ution% The mixture 6as stirred thorough y as the precipitated soap 6as co ected using a f uted fi ter paper% The product 6as 6ashed t6ice 6ith $+2m= portions of co d disti ed 6ater% * grams of crude soap 6as disso .ed in $+2 m= portions of co d disti ed 6ater and 6as set aside for tests% The remaining soap 6as p aced in an e.aporating dish, heated in a 6ater )ath 6ith constant stirring, unti it formed a thic7 so ution% To account for the physica properties of the product, the appearance, co or, texture, and odor 6ere recorded a ong 6ith its me ting point% Chemica tests 6ere done on the fina product% The product/s p' 6as o)tained using a itmus paper% $2m= of di ute ca cium ch oride 6as added to $+2m= of the soap so ution% The same procedure 6as done using di ute magnesium ch oride and ferric ch oride so utions% 'ydroch oric acid 6as added to >+2m= of the soap so ution unti it is an acid to Congo red% The mixture 6as coo ed and the precipitates 6ere co ected in a f uted fi ter paper% The fina product 6as tested for so u)i ity in *2m= methy ene ch oride% C. Synthesis of Aspirin T6o grams of sa icy ic acid 6ere p aced in a $*>2Er enmeyer f as7% Bi.e mi i iters of acetic anhydride and > drops of E>D phosphoric acid 6ere added% The f as7 6as heated in the hot 6ater )ath for > minutes% 0fter remo.ing from heat and 6hi e sti hot, * m= of 6ater 6as added% 0fter decomposition is comp ete, ?+ m= of 6ater 6ere added unti crysta s )egin to form% The product 6as co ected )y suction fi tration% The product 6as 6ashed and dried% 1t 6as then recrysta i-ed from #> m= of hot 6ater 6ith the use of deco ori-ing charcoa and then 6eighed% 1n testing the products for physica properties, the appearance, co or, texture, and odor of the product 6ere noted% 1ts me ting point 6as a so determined% Bor chemica tests, a fe6 crysta s of aspirin 6ere disso .ed in $ m= of methano in a test tu)e and $D ferric ch oride so ution 6as added% The test 6as repeated using sa icy ic acid% The resu ts 6ere recorded% V. Results A. Synthesis of dye Chem #$%$, Synthesis of Organic Compounds

$% 0ctua and percentage yie d 6ere not noted anymore% *% Physica properties of the product: 0ppearance: fine po6der Co or: orange2red Texture: fine, po6dery Odor: paint 3)ut it shou d )e odor ess5 &e ting point: $#$2$#* C #% Chemica tests: Table 1 :esu ts for the chemica tests done on the product )ased on o)ser.ations Test Performed O)ser.ation

+%$ & CaO'

=east intense

+%$ & 'C

&ost intense &oderate y intense 1ntense



B. Synthesis of soap $% 0ctua and percentage yie d 6ere not noted anymore% *% Physica properties of the product: 0ppearance: s ushy 6hite su)stance Co or: 6hite Texture: soft Odor: sme s i7e ethano &e ting point: $#>2$?>C 3theoretica 5

#% Chemica test:

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Table 2 :esu ts for the chemica tests done on the product )ased on o)ser.ation

ch oride and the process is ca ed dia-oti-ation% The reaction is sho6n )e o6%


Test Performed


+ benzene diazonium chloride


2 H2O

nitrous acid


)asic Bormation of precipitate FCh#3C'*5$?CO*2G* CaH H *CaH FCh#3C'*5$?CO*2G* &gH H *CaH FCh#3C'*5$?CO*2G# BeH H #CaH misci) e

%i&ure 1% (ia-oti-ation process The nitrous acid in the reaction is from the reaction of 'C and CaCO*% 1t is formed prior to its use )ecause it is .ery unsta) e% The dia-oti-ation reaction yie ds a .ery reacti.e sa t, the pheny dia-onium ch oride%

Ca cium ch oride &agnesium Ch oride Berric ch oride

Oi 6ith soap

%i&ure 2% Pheny dia-onium Ch oride Pheny dia-onium ch oride so ution 6as then reacted 6ith 2naphtho in CaO'% The reaction is ca ed dia-onium2coup ing reaction, in 6hich the dia-onium sa t attac7s the car)on in the ortho2 and para2 positions 6ith respect to the acti.ating group attached to the )en-ene% 1n the experiment, the 2 naphtho coup es 6ith the dia-onium sa t%

Oi 6ith 6ater

immisci) e

C. Synthesis of Aspirin $% The actua and percentage yie d 6ere not noted anymore% *% Physica properties of the product: 0ppearance: fine po6der Co or: 6hite Texture: fine Odor: odor ess &e ting point: $#IC 3theoretica 5 #% Chemica test: ,pon the addition of ferric ch oride, the product shou d not produce a purp e co or if a the sa icy ic acid has )een used up in the reaction% VI. Discussion

%i&ure '% :eaction of dia-onium sa t 6ith J2 naphtho

A. Synthesis of Dye The synthesis of $2Pheny a-o2*2naphtho , or Sudan $, in.o .es t6o steps: the first )eing the preparation of a so ution of dia-onium sa t, )en-ene dia-onium ch oride from ani ine% 1n this process, the ani ine reacts 6ith sodium nitrate in extreme y acidic medium )y using 'C or '*SO?% The reaction yie ds pheny dia-onium Chem #$%$, Synthesis of Organic Compounds

The reaction mechanism is further sho6n )e o6%

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%i&ure ). Sudan2$ B. Synthesis of soap This in.o .es the a 7a ine hydro ysis 3reaction 6ith 6ater or di ute a 7a i5 of trig yceride 3fat or oi 5% Trig yceride is reacted 6ith ye 3CaO' so ution5 or other strong )ases such as NO' to produce g ycero and fatty acid sa ts% The fatty acid sa t is the soap% Saponification is the term used 6hen hydro ysis of esters are done to produce soap%

%i&ure 2% :eaction mechanism for dia-onium sa t K J2naphtho reaction The second structure is the intermediate formed 6hich is sta)i i-ed )y resonance% The dia-onium sa t attac7ed the car)on in the ortho2position )ecause there are many resonance structures possi) e for the product% 1f there are many resonance structures, the product is more sta) e, that is 6hy the attac7 at the ortho2 position is more fa.ored% %i&ure *. Structure of trig yceride The ester functiona groups are hydro y-ed re easing its a coho portion as g ycero and the acid portions as a mixture of the sodium sa ts of the fatty acid% The g ycero is 6ater2so u) e and is separated from the fatty acid sa ts% These are near y inso u) e in 6ater, and are 6ashed and compressed into a ca7e O 6hich is the soap% The reaction is sho6n )e o6%

%i&ure (% Some of the resonance structures of the product The compound that is formed is $2 pheny a-o2*2naphtho or LSudan2$M, a precipitate that is orange2red in co or% Chem #$%$, Synthesis of Organic Compounds

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%i&ure +% :eaction of fat and ye 3Saponification5 The )ond )et6een the fatty acid and the g ycero )ac7)one is referred to as an ester in7age% 1n the saponification process, the ester in7age is )ro7en to form g ycero and soap% The reaction mechanism is )ased on nuc eophi ic acy su)stitution% 1t is easier to oo7 at a simp e ester than a fat to i ustrate ho6 the mechanism 6or7s%

this reaction, the hydroxide or a 7oxide ions5, this reaction is not re.ersi) e% Sodium and potassium sa ts are genera y so u) e in 6ater, and potassium soaps are usua y softer than sodium soaps% 9hen these meta s are rep aced )y ca cium, iron, or magnesium ions, the ne6 car)oxy ate sa ts are no onger so u) e in 6ater; and form 6hat 6e refer to as Lsoap scumM% Pou may ha.e heard of the terms Qhard 6aterQ or Qsoft 6aterQ% 'ard 6ater is 6ater that contains many meta ions such as iron, ca cium, and magnesium ions% Soft 6ater contains ess of these ions% Therefore, 6hen 6e use soap 6ith hard 6ater, these ions rep ace the sodium or potassium ions% C. Synthesis of Aspirin 0spirin or acety sa icy ic acid is prepared )y reacting sa icy ic acid 6ith acetic anhydride in a process ca ed esterification% Esterification is the acid2cata y-ed reaction of a car)oxy 32COO'5 group and an 2O' group of an a coho or pheno to form a car)oxy ate ester% The fo o6ing reaction i ustrates ho6 aspirin is synthesi-ed%

%i&ure ,% Birst step in the reaction mechanism 'ere, the hydroxide ion from CaO' attac7s the car)ony group of the ester to gi.e an orthoester%

%i&ure 1-% Second step in the reaction mechanism The orthoester rearranges to form a car)oxy ic ester and an a 7oxide%

%i&ure 1'% O.era reaction for aspirin %i&ure 12% Third step in the reaction mechanism Proton transfer ta7es p ace since the O: group is more )asic than :COO'% The products formed are a coho and sa t% 1n saponification, the a coho is the g ycero and the sa t of the fatty acid is the soap% (ue to the sta)i ity and ac7 of reacti.ity of the car)oxy ate anion 6ith most nuc eophi es 3in Chem #$%$, Synthesis of Organic Compounds The 2O' group is the pheno ic 2O' group attached to ring of the sa icy ic acid% The acety group, 2COC'# comes from acetic anhydride, and the reaction is cata y-ed )y phosphoric acid% The reaction mechanism is sho6n )e o6%

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)ecause of its po ar and nonpo ar ends% 'o6e.er, in the presence of meta ions, precipitate forms% The reaction mechanism is )ased on nuc eophi ic acy su)stitution% To synthesi-e 0spirin, the reaction ca ed esterification 6as done )y reacting acetic anhydride 6ith sa icy ic acid% The reaction mechanism in.o .es fi.e steps% Some of the reagents used in the experiment are corrosi.e so it is important to fo o6 instructions and 6ear gogg es or g o.es% Separate droppers for each reagent must )e used to a.oid contamination% 1t is a so important to fo o6 6hat the manua says to produce good a)oratory resu ts and yie d as much product as possi) e%


%i&ure 12% :eaction mechanism for the synthesis of 0spirin

The 'H from an acid cata yst protonates the car)ony oxygen of acetic anhydride to ma7e the car)ony groups more suscepti) e to nuc eophi ic attac7% This is fo o6ed )y the attac7 of the nuc eophi e, the pheno ic group, to the car)ony group to 6hich the protonated oxygen is attached% Proton transfer fo o6s% The hydrogen from the pheno ic group of the nuc eophi e forms a )ond 6ith the oxygen ad<acent to the car)on that is dou) y )onded to another oxygen% 0cetic anyhydride is formed )y the departure of the ea.ing group% Bina y, proton transfer happens again to form acety sa icy ic acid% The 'H is regenerated% The main impurity or )y2product for the reaction is excess sa icy ic acid, 6hich 6i co2precipitate 6ith the 0spirin if the procedure is done too quic7 y% To assess the purity of the product, ferric ch oride is used% 1t reacts 6ith pheno to form a purp e so ution% 1f the product turns gi.es a purp e co or 6ith ferric ch oride so ution, it means that not a of the sa icy ic acid has )een consumed% Thus, the product is impure% VII. #" #./0I" 0 A D RE#"11E DATI" 0 To synthesi-e dye, the pheny dia-onium ch oride 6as produced )y reacting ani ine 6ith nitrous acid and reacted 6ith naphtho % The reaction in.o .ed are dia-oti-ation and dia-onium2coup ing reactions% To synthesi-e soap, saponification 6as emp oyed 6here fat is hydro y-ed 6ith ye to produce a sa t of the fatty acid% The sa t is 6hat 6e ca soap% 1t is a .ery effecti.e emu sifying agent Chem #$%$, Synthesis of Organic Compounds

Jruice, P% P% Essential Organi Che!istry , *++I, Pearson Eduation, 1nc% 9i iamson, N%=% "a ros ale and "i ros ale Organi E#peri!ents$ *nd Ed% $99?, 'oughton &iff in, Joston :e.ised IR*ER+8% E#peri!ent %& Synthesis of Soap (Saponifi ation) :etrie.ed from http:RRorganicchem%orgRoc*6e)R a)RexpRsoa pRsoapprep%pdf Septem)er 8, *+$+ http:RR666%scri)d%comRdocR*89II#88RSynth esis2of20spirin :etrie.ed 0ugust #$, *+$+ http:RR666%reachoutmichigan%orgRfunexperi mentsRquic7RcsustanRaspirin%htm retrie.ed 0ugust #$, *+$+ http:RR666%aspirin2 foundation%comRcardio*%htm 0ugust #$, *+$+


9e here)y certify that 6e ha.e gi.en su)stantia contri)ution to this report: 2222222222222222222222222222 Thatcher Pancho 222222222222222222222222222222 !erome 0% Sadudaqui

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