Group Members: Curso, Mark Anthony R. "ambo#on, Cyril Marie $. %ro, Cly&e 'rin(ess )him *.
Date of Experiment: April 25, 2!5
Experiment +o. Acyl Compounds: Soap and Detergents
I.
Result sultss and and Discu scussio sions.
-olubility an& A(i&ity of Carboxyli( A(i&
-ample
-olubility eha/ior
lue "itmus 'aper to:
A(eti( A(i&
soluble
re&
en0oi( A(i&
insoluble
re&
-o&ium en0oate
soluble
blue
A(eti( a(i& an& so&ium ben0oate 1ere both soluble in 1ater 1hile the ben0oi( a(i& 1as not. Carboxyli( Carboxyli( a(i&s form ne1 (arbony (arbonyll (ompoun& 1hen 1ater is a&&e& to it by nu(leu nu(leuphili phili(( a(yl substitution. C% bon& in ben0oi( a(i& is ele(tron3ri(h 1hi(h ma&e it unrea&y to rea(t 1ith the nu(leophile, 1ater. 4n a(eti( a(i& an& so&ium ben0oate, their C% bon& is ele(tron3poor makin it rea&y to rea(t 1ith the nu(leuphile, 1ater.
Relati/e A(i&ities of Carboxyli( A(i&s an& 'henols
-ample
-olubility in !6 +a%7
!6 +a7C%8
en0oi( A(i&
-oluble
-oluble
'henol
-oluble
4nsoluble
Carboxyli( a(i&s are soluble in &ilute solutions of both stron a(i& an& stron base. en0oi( a(i& is a (arboxyli( orani( a(i& (ompoun&, thus, it is soluble in !6 +a%7 an& !6 +a7C%8. %n the othetr han&, phenols are soluble in &ilute solutions of stron base but insoluble in &ilute solution of !6 +a7C%8.
7y&rolysis of A(yl Compoun&s
-ample
Rea(tion 1ith 72%
After heatin
lue "itmus 'aper to:
A(etyl Chlori&e
Clou&y, bubbles forme&
+o (hane
re&
A(eti( Anhy&ri&e
Clear, homoeneous
+o (hane
re&
en0ami&e
insoluble
Dissol/e&, (lear solution
re&
A(etyl (hlori&e rea(ts 1ith 1ater to yiel& (arboxyli( a(i& by substitutin the 3Cl 1ith 3%7. A(i& anhy&ri&e rea(ts 1ith 1ater formin t1o a(i&s. Rea(tion of ben0ami&e an& 1ater re9uires heat to yiel& a(i& an& amine. A(etyl (hlori&e, a(eti( anhy&ri&e an& ben0ami&e are a(i&i(. Ethyl ben0oate is basi(. Comparison of -oap an& Deterent
-ample
7y&rolysis Re& "itmus 'aper to:
lue litmus 'aper to
-oap
blue
blue
Deterent
blue
blue
Rea(tion 1ith 7Cl
Rea(tion 1ith -oft 72%
7ar& 72%
Clou&y li9ui&
Clear li9ui& 1ith bubbles
Clou&y li9ui& 1ith suspen&e& parti(les an& smaller bubbles
Clear li9ui&
Clear li9ui& 1ith bubbles
Clear li9ui& 1ith bubbles
-oap an& &eterents are alkaline solutions thus it 1ill i/e a blue (olor to a litmus paper. -oap solutions are foun& to ha/e a turbi& solution 1hile &eterents ha/e a (lear solution in 7Cl. -oap in soft 1ater resulte& to a (lear li9ui& sin(e it is an effe(ti/e (leanser on soft 1ater. -oap in har& 1ater has a (lou&y li9ui& sin(e it is an ineffe(ti/e (leanser in har& 1ater. %n the other han&, &eterent is an effe(ti/e (leanser in both soft an& har& 1ater, as a result, (lear li9ui& is obser/e& in &eterent in both soft an& har& 1ater. Emulsifyin Rea(tion -ample
%bser/ations
-oap
1o &istin(t layers, 1hite parti(les on upper part,1hite li9ui& in lo1er part an& smaller bubbles formes
Deterent
1o &istin(t layers, 1hite li9ui& on the upper part slihtly (lou&y li9ui& on lo1er part an& bubble1 forme&
;ater
+o emulsifi(ation
Deterent has more emulsifi(ation than soap 1hile 1ater has none.
II. Calculations. There are no calculations in this experiment. III. Questions and Answers.
!. Explain the &ifferen(e in the solubility of ben0oi( a(i& an& so&ium ben0oate in 1ater. ;hi(h of the t1o 1oul& you pre&i(t to be more soluble in C7Cl8< Explain Carboxyli( a(i&s form ne1 (arbonyl (ompoun& 1hen 1ater is a&&e& to it by nu(leuphili( a(yl substitution. C% bon& in ben0oi( a(i& is ele(tron3ri(h 1hi(h ma&e it unrea&y to rea(t 1ith the nu(leophile, 1ater. hus, ben0oi( a(i& is insoluble in 1ater. 4n a(eti( a(i& an& so&ium ben0oate, their C% bon& is ele(tron3poor makin it rea&y to rea(t 1ith the nu(leuphile, 1ater. hus, a(eti( a(i& an& so&ium ben0oate are soluble in 1ater. 2. ase& on the results in 'art A.2, 1hat (an be sai& about the relati/e a(i&ities of phenols an& (arboxyli( a(i&s< Arrane the follo1in (ompoun& types in or&er of in(reasin a(i&ity: (arboxyli( a(i&, al(ohol, phenol an& 1ater. Carboxyli( a(i&s are mu(h more a(i&i( than al(ohols e/en thouh both (ontain %=7 roup &ue to the relati/e stabilities of (arboxylate anions an& alkoxi&e anions. 4n (arboxylate ion, the neati/e (hare is &elo(ali0e&, or sprea& out o/er both oxyen atoms 1hile in alkoxi&e ion, the neati/e (hare is lo(ali0e& on one oxyen atom only. hus, a (arboxylate ion is a stabili0e& resonan(e hybri& of t1o e9ui/alent stru(tures. 'henols are more a(i&i( than al(ohols be(ause the phenoxi&e anion is resonan(e3 stabili0e& by the aromati( rin. -harin the neati/e (hare o/er the rin in(reases the stability of the phenoxi&e anion an& thus in(reases the ten&en(y of the (orrespon&in phenol to &isso(iate. 7o1e/er, 1ater is more a(i&i( than al(ohol be(ause 1ater (an &elo(ali0e its neati/e (hare. herefore, (arboxyli( a(i&s > phenols > 1ater > al(ohols in terms of their a(i&ities. 8. ase& on the results in 'art , arrane the follo1in (ompoun& types in or&er of &e(reasin hy&rolysis rate: a(i& hali&es, a(i& anhy&ri&es, esters an& ami&es. Gi/e theoreti(al explanations for the obser/e& &ifferen(es in rea(tion rates. ase& on the results in part , a(i& hali&es ha/e the hihest hy&rolysis rate be(ause a(i& hali&es are polar, an& the more hihly polar (ompoun& are the more rea(ti/e it is. A(i& hali&es is also the most rea(ti/e be(ause it stronly polari0es the (arbonyl roup &ue to its ele(troneati/ity. A(i& anhy&ri&es are next in or&er be(ause it rea(ts #ust like the a(i& hali&es, but in a slo1er rate. Durin the nu(leophili( a(yl substitution step, only half of the mole(ule is use& an& the other half a(ts as the lea/in an& pro&u(es a by3pro&u(t (alle& (arboxylate anion. Esters are next in or&er be(ause it also rea(ts in the same manner 1ith the first t1o (ompoun&s, althouh esters are less rea(ti/e to1ar& nu(leophiles than a(i& (hlori&es or anhy&ri&es. he last in or&er are the ami&es be(ause they ha/e a /ery stable linkae enouh to ser/e as the basi( unit from 1hi(h proteins are ma&e.
?. 4s the soap 1ater mixture a true solution< Cite examples to support your ans1er.
he soap 1ater mixture is not a true solution but a (olloi&al mixture. he soap 1ater mixture is a (lou&y mixture 1here one substan(e is e/enly &isperse& throuhout one another. ;ith this, some (olloi&s are mistaken to be true solutions &ue to their similar appearan(es. 5. ;hat is a (olloi&al mixture< 7o1 &oes a (olloi&al mixture arise 1hen soap is mixe& 1ith 1ater< A (olloi&al mixture is a mixture that has t1o subsatn(es e9ually or e/enly &isperse& 1ith ea(h other. A (olloi&al mixture has an outer layer 1ith the same (hares (ausin them to repel ea(h other resultin to lesser areation to form parti(les that are lare enouh to pre(ipitate. he non3polar hy&ro(arbon tail of the soap &issol/es into the oil, a non3polar hy&ro(arbon, formin spheri(al (luster (alle& mi(elles. Mi(elles@ neati/ely (hare& surfa(es are 1here &roplets of oil are solubili0e& in 1ater 1here they be(ome (oate& by the hy&rophobi( non3polar tails of soap mole(ules. As a result, a (olloi&al misture of soap31ater mixture arise. . %n the basis of the litmus test, are the soap31ater an& &eterent31ater mixtures a(i&i(, basi( or neutral< Explain the &ifferen(e, if any of the rea(tions of the soap31ater an& &eterent31ater mixtures to litmus paper. Rea(tion of both soap31ater an& &eterent31ater mixtures to litmus paper sho1s their alkalinity. -oaps ten& to be alkaline after they un&ero hy&rolysis rea(tion upon hy&ration. Deterent31ater mistures are also alkaline in a lesser &eree. B. ;hi(h 1oul& you pre&i(t to ha/e a reater emulsifyin po1er in har& 1ater, soaps or syntheti( &eterent. Explain. -yntheti( &eterents ha/e a reater emulsifyin po1er in har& 1ater@@ be(ause it &oes not form pre(ipitates 1hen intro&u(e& 1ith the (al(ium an& manesium ions. his is &ue to the presen(e of sulfonate roup in &eterents, 1hi(h (annot be foun& in soaps. . Explain the (leanin property of soaps an& &eterents base& on your obser/ations of their emulsifyin a(tion. he soaps@ an& &eterents@ ability to emulsify or &isperse 1ater3insoluble (ompoun&s an& hol& them in suspension 1ith 1ater is a result of their (leanin a(tion. ;hen a soap or &eterent is a&&e& to 1ater that (ontains 1ater3insoluble (ompoun&s, the soap or &eterent mole(ules sorroun& the 1ater3insoluble (ompoun&s. he 1ater3insoluble (ompoun&s are then &issol/e& in the alkyl roups of the soap or &eterent mole(ules 1hile their ioni( en& allo1s the mi(elle to &issol/e in 1ater. IV. Conclusion
he roup (ompare& the a(i&ities of (arboxyli( a(i&s an& phenols an& foun& out that (arboxyli( a(i&s are more a(i&i( than phenols, this is &ue to the relati/e stabilities of (arboxylate anions an& alkoxi&e anions. he roup also prepare& soap an& learne& that preparation of su(h is by saponifi(ation of fats. he roup also (ampare& the properties of soap an& &eterents an& foun& out that &eterents (ompare& to soap are more effe(ti/e in har& 1ater.
