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AmilPatel

OrganicChemistryPostLab
Experiment3
Preparationof4bromo2chloroacetanilide
ReactionScheme

2NaClO3+12HCl7Cl2+6H2O+Na+

ProceduralFlowChart

Results
Figure1:TheoreticalYield

bromoacetanilide1 mol
1 mol 4bromo2 chloroacetanilide
214.062 g

4bromoacetanilide
Theoretical Mass of product :10.7 g of 4
1 mol

Actual Mass=4.29 grams


Percent Yield=

Actual Mass
4.29 g
100=
100=34.5
Theoretical Mass
12.42 g

Table1:MeltingPoint
ExperimentalMeltingPoint
151152.9C

ActualMeltingPoint
151152C*

*ObtainedfromCengage
(http://www.cengage.com/chemistry/book_content/049501334X_gilbert/prelabs/a_e_msds_gilbert_withtoc
.htm_Toc122243199)

Figure3:4bromoacetanilideFTIR

Table2:4bromoacetanilideFTIRanalysis
Wavenumber(s)
Bond
(cm1)
1392
AromaticCC
1434
stretch
1487
1602

LiteratureData(cm1) Strength(s)
Respectively)
15001400
S
15001400
S
15001400
S
16001585
S

691
741
820
3065
3123.5

AromaticCH
stretch

900675
900675
900675
31003000
31003000

M
S
S
W
W

691
741
820
3263
3300
1668

NHwag/NH
stretch

910665
910665
910665
34003250
34003250
17601665

M
S
S
M
M
M

13351250
13351250
11751000
833810

S
S
M
S

1258
1310
1005
820

CarbonylC=O
stretch
CNstretch
ArylCBrstretch
1,4disubstituted

benzenestretch

Figure4:4bromo2chloroacetanilideFTIR

Table3:4bromo2chloroacetanilideFTIRanalysis
Wavenumber(s)
Bond
LiteratureData(cm1)
(cm1)
1470
AromaticCC
15001400
1517
stretch
15001400
1579
16001585
681
750
865
3027
3077

AromaticCH
stretch

900675
900675
900675
31003000
31003000

Strength(s)
Respectively)
S
S
S
S
S
S
W
W

681
750
865
3241
3275
1663
1251
1297
1008
1058
1080
1145
1008
1058
1080
1145
815
865

NHwag/NH
stretch

910665
910665
910665
34003250
34003250
17601665

S
S
S
M
M
S

ArylCBrstretch

13351250
13351250
11751000

ArylCClstretch

11751000

1,2,4trisubstituted
benzenestretch

900800

S
S
M
S
M
W
M
S
M
W
S
S

CarbonylC=O
stretch
CNstretch

Allliteraturedataobtainedfromorgchem.colorado.eduandfaculty.augie.edu
(http://orgchem.colorado.edu/Spectroscopy/specttutor/irchart.pdf)
(http://faculty.augie.edu/~duffy/irareaschem201.pdf)

Discussion

Forthisexperiment,anelectrophilicaromaticsubstitutionisperformedinorderto
chlorinate4bromoacetanilideandprepare4bromo2chloroacetanilide.The2chloro
isomerisformedbecauseofthestrongdirectingpoweroftheacetamidogroup;Even
thoughtheacetamidogroup(anactivatinggroup)andthebromogroup(adeactivating
group)directsubstitutiontorespectiveorthoandparasites,theacetamidogroupis
significantlystrongerthanthebromogroupsothechlorineissubstitutedonthe2
positioninsteadofthe3position.
Aftercomparingtheexperimentalmeltingpointwiththeactualmeltingpointof
4bromo2chloroacetanilide,therewasverylittlediscrepancyindicatingthattheproduct
hadverylittleimpuritiesinit.Apotentialerrorthatcouldhaveseverelyaffectedthe
meltingpointcouldhavebeenthattherewasasignificantamountofunreacted4
bromoacetanilideinthefinalproduct.Eventhough4bromoacetanilideisreactionand
canperformanelectrophilicaromaticsubstitutionreaction,itisnotasreactiveas
acetanilideandthepotentialofhavingunreacted4bromoacetanilideisapossibility.The
meltingpointof4bromoacetanilideisbetween165and169degreesCelsiussoif
unreacted4bromoacetanilidewaspartofthefinalproduct,theexperimentalmelting
pointwouldhavebeen510degreeshigherthanexpected.Butbecausethedifferencein
experimentandactualmeltingpointsisonlya.9degreedifference,thedatasuggeststhat
averypurefinalproductwasproduced.

AfteranalyzingtheFTIRsforboththestartingmaterialandthefinalproduct,
theresultssuggestaswellthatapurefinalproductwasproduced.Thebiggestdifference
between4bromoacetanilideand4bromo2chloroacetanilideistheadditionofachloro
groupontothebenzenering.SinceArylBrandArylClstretcheshavethesamerange,
itwasveryeasytospotthedifferencesbetweenthestartingmaterialandthefinal
product.Thestartingmaterialhadonly1peakbetween1175cm1and1000cm1
showingonlytheadditionofabromogroupontheacetanilide.ThefinalproductsFTIR
show4peaks(1008cm1,1058cm1,1080cm1,1145cm1)suggestingthatbothbromo
andchlorogroupswereonthebenzenering.Alsowiththeextrasubstituentonthe
benzenering,theringwentfrombeing1,4disubstitutedtobeing1,2,4trisubstituted
andthatcanalsobeseenintheFTIRresults.Thestartingmaterialhadonly1peak
insidethedisubstitutedbenzenestretchat815cm1.The4bromo2chloroacetanilide
hadaverysimilarstrongpeakat820cm1alongwiththeadditionofanotherstrongpeak
at865cm1indicatingtheadditionofanothergroupontothebenzenegroup.
Theonlyblemishontheresultsachievedduringtheexperimentistheextremely
lowyield.Thelowyieldcouldbeattestedtotherecrystallizationdoneaftertheinitial
vacuumfiltrationbecausetheoriginalprecipitatewasveryyellowandhadalotofcrude
material.Eventhoughtherecrystallizationcouldhaveaffectedtheyieldnegatively,it
wasasignificantreasonforthehighpurityinthefinalproduct.Iwouldimprovethe
experimentbymakingtherecrystallizationstepnecessaryinsteadofitbeinga
recrystallization.Therecommendedrecrystallizationwasthereasonforthestrong

resultseventhoughtheyieldwasaffected.Overalltheexperimentwentverywelland
theresultssuggestthesame.

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