experiment 8 - the preparation of acetanlide

8/9/2019 Experiment 8 - The Preparation of Acetanlide

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DEPARTMENT OF PURE AND APPLIED CHEMISTRY

Visayas State University, Baybay, Leyte

CHEM!" Or#ani$ C%e&istry II

Lab'rat'ry Re('rt

Na&e ) Mark Ryan R. Tripole Date Per*'r&e+ ) 01/20/2015

C'rse-Yr ) BS Chemistry II Date Sb&itte+ ) 01/29/2015

.r'( N' ) 2 S$'re

E/(eri&ent N'0 1

T%e Pre(arati'n '* A$etani2i+e

I0 Intr'+$ti'n

Acetanilie! a compo"n also kno#n $y its I%&AC name as either '(phenylacetamie or '(phenylethanamie! is an oorless soli chemical that has either a lea) or a )lake like appearance.The crystals o) acetanilie are #hite in color an it is only sparin*ly sol"$le in #ater! $"t more orless sol"$le in other sol+ents like iethyl ether! ethanol! $en,ene an acetone. -ookin* at thepast applications in the compo"n! acetanilie #as consiere to $e the )irst aniline eri+ati+ethat #as )o"n to possess anal*esic as #ell as anti(in)lammatory properties an $eca"se o) this#as incl"e as a sta$le in meical practice "ner the trae name Anti)e$rin. B"t then it #as)o"n to ca"se a conition kno#n as cyanosis characteri,e $y the p"rple coloration o) the skin"e to the tiss"es near the s"r)ace ha+in* lo# oy*en sat"ration an #as iscontin"e an less)a+ore o+er m"ch less toic aniline eri+ati+es s"ch as phenacetin #hich #as also e+ent"ally)o"n to $e potentially carcino*enic. In its o#n ri*ht! acetanilie is not an anal*esic! $"t is

rather meta$oli,e in the $oy into acetaminophen! also #ell kno#n as &aracetamol. Acetaniliealso )o"n its #ay into photo*raphy in its eperimental "se as photo*raphic e+elopers.+ent"ally! the commercial "sa*e o) acetanilie has ie o#n an most o) its "sa*e is in+ol+e#ith or*anic synthesis! $ein* a prec"rsor in the synthesis o) penicillin an a host o) otherpharmace"ticals. Its closest "se in toays commercial spectr"m is as an inhi$itor that slo#s theecomposition o) r"*(store hyro*en peroie sol"tions.

The synthesis o) acetanilie comes a$o"t $y the acylation o) aniline #ith car$oylic acisor their eri+ati+es to *i+e an amie pro"ct. Tho"*h there are 3"ite a n"m$er o) methos intothe synthesis o) the compo"n! the most common la$oratory proce"re that is pop"larly "se inintro"ctory or*anic chemistry co"rses is thro"*h the acylation o) aniline #ith acetic anhyrie.The o$4ecti+e o) the eperiment #as to *ain )amiliari,ation o) the la$oratory process in thesynthesis o) acetanilie! as #ell as *ain )amiliari,ation o) the mechanisms $ehin the process o)

acylation e)ine as the process o) ain* an acyl *ro"p to a compo"n. Another o$4ecti+e o)this eperiment #o"l $e to o$tain ae3"ate kno#le*e into the $asic ieas an concepts $ehineach partic"lar portion o) the eperiment an #hy certain steps are in+ol+e.

II0 Res2ts

Sho#n in the s"cceein* pa*es are the res"lts $ase on the eperiment! the ata o$tainethro"*h the per)ormance o) the proce"re an relate calc"lations.

&a*e 1 o) 12


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Calculation of number of moles of acetanilide produced to determine limiting reagent:

Aniline

'o. o) moles o) acetanilie

'o. o) moles o) acetanilie 0.216 moles

Acetic Anhydride

'o. o) moles o) acetanilie

'o. o) moles o) acetanilie 0.257 moles

Since it is the aniline that pro"ces the smaller amo"nt o) the acetanilie! then it is the limitin*rea*ent that #ill etermine the amo"nt o) the )inal pro"ct.

&a*e 2 o) 12

1 mol acetanilie

1 mol aceticanhyrie

28 *rams acetic anhyrie

1 mol aceticanhyrie

102.09 * aceticanhyrie

20 *rams aniline 1 mol aniline

97.12 *rams aniline

1 mol acetanilie

1 mol aniline


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Calculation for theoretical yield for acetanilide:

Theoretical yiel 0.216 mol acetanilie

Theoretical yiel 2.92 *rams acetanilie

Calculation of percentage yield based on actual yield:

Act"al yiel 6.5 *rams

&ercenta*e yiel 100:

&ercenta*e yiel 100:

&ercenta*e yiel 15.15 :

;"rther ela$oration on the res"lts shall $e *i+en in the net section o) this la$oratory report.

III0 Dis$ssi'n

Sho#n $elo# is a simple schematic ia*ram o) the eperimental proce"re per)orme.

&a*e 7 o) 12

175.18 *rams acetanilie

1 mol acetanilie

Act"al yiel

Theoretical yiel

6.5 *rams

2.92 *rams


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The reaction as sho#n in the proce"re is characteristic o) an aition o) an acyl *ro"p toa compo"n. ;or this partic"lar reaction! the acylatin* *ro"p is the acetic anhyrie an theaniline is the compo"n to $e ae to. The *eneral e3"ation )or the reaction is sho#n $elo#

experiment 8 - the preparation of acetanlide

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