NattanitTrakullapphan(Nam)

[2]
Amoxicillin

Molecularformula:
C
H
N
O
S
16
19
3
5
IUPACname:
(2S,5R,6R)6[[(2R)2amino2(4hydroxyphenyl)acetyl]amino]3,3dimethyl7oxo4thia1azabi
cyclo[3.2.0]heptane2carboxylicacid

Figure1

the2Dstructureofamoxicillin

Amoxicillinisapenicillintypeantibioticinternallyusedtotreatbacterialinfections
,
suchastonsillitis,bronchitis,pneumonia,gonorrhea,andinfectionsoftheear,nose,throat,
skin,orurinarytract
,butnotviralinfectionsbyinhibitingthegrowthofbacterialcellwalls
andkillingthem.Itisoccasionallyusedtogetherwithothermedicationstotreatother
certainulcers.Experimentallyandcomputably,ithasphysicochemicalpropertiesasstatedin
[4]
table1
beneath.
[2][4][5]
Table1

PhysicalandChemicalPropertiesofAmoxicillin

PhysicalProperties

ChemicalProperties

Molecular
Weight

365.40416g/mol

Watersolubility

ExactMass

365.104542g/mol

pH

Monoisotopic
Mass

365.104542g/mol

3430mg/L
4.44.9(0.25%w/v
solution)

Odor

Penicillintypeodor,
slightsulphurousodor

Color

White,oralmostwhite

Appearance

Powder/Crystalline
solid

Taste

bitter

Meltingpoint

194C

NattanitTrakullapphan(Nam)

Boilingpoint
Density
Specificoptical
rotation

743.2C

320g/mL

+290to+315

Amoxicillincontains5functionalgroupsinitsownasstructurein
figure2
below.
Theyarephenol,amine,amide,thioether,andcarboxylicacid.

Figure2
Functionalgroupspresentinamoxicillin
Withthesevariousfunctionalgroups,amoxicillincanundergomanychemicalreactions,in
whichdifferentfunctionalgroupsareresponsiblefordifferentchemicalreactions.Dueto
thedifferentresultsendedup,thefunctionalgroupscanbedeterminedusingdistincttests.
Somefunctionalgroupsmaybetestedusingthesamemethods,butdifferentresultsare
showntodefinethefunctionalgroups.Forinstance,thetestforcarboxylicacidandphenol
canbedonesimilarlyusingsolubilitytest.Butbecausecompoundcontainingoxygencan
sometimesbesolubleinwaterandsometimesbeinsolubleinwater,othersolubilitytests
arenecessary,accordingto
figure3.
Fortunately,carboxylicacidcanbeidentifiedafter
testedwith5%NaHCO
3nomatterifitissolubleinwater.Bothwatersolubleand

waterinsolublecarboxylicacid,issolublein5%NaHCO
,formingCObubblesasshownin
3
figure4a
.Ontheotherhand,testingphenolwith5%NaHCO
givesnegativeresultoritis
3
[6]
notsoluble.IfnotanditisinsolubleinNaOH,itisphenol.However,usingsolubilitytest,
twotestsareneededforphenol.Therefore,Iron(III)chloridehadbettertestphenols,which
[1]
isdoneonlyinonetest.
PhenolsreactingwithFeCl
3giveared,blue,green,orpurplecolor

afteraddingpyridineasin
figure4b
.Inaddition,similarlytocarboxylicacid,aminesare
determinedusingsolubilitytestofHClshownin
figure4c
.IfthecompoundisHClsoluble,it
isanamine.Lastly,totestthioethersorsulfides,aclassificationtestisproceeded.The
sulfide,inalcoholsolution,isaddeddropwisetoasaturatedsolutionofmercuricchloridein
[7]
alcohol.
Accordingto
figure4d,
asaresult,thesulfidesprecipitatesimmediately,give
crystalline.Generally,thesetestsareselectedbecausetheycouldbedonesimplyinone
step,andthereagentsusedarebasicallyknownforbasicChemistry.

NattanitTrakullapphan(Nam)

Figure3
thischartshowsthemethodtoidentifythefunctionalgroupofanunknown
[7]
compoundusingsolubilitytest.

Figure4
Theredlabelsindicatethechangeinthefunctionalgroupbeforeandafterthe
reaction.

NattanitTrakullapphan(Nam)

References
[1]Doe,N.(2014).
Testsforphenolsandnitrogroups.

Retrievedfrom

http://academics.wellesley.edu/Chemistry/chem211lab/Orgo_Lab_Manual/Appendi
x/ClassificationTests/phenol_amine_nitro.html

[2]Kaur,S.P.,Rao,R.,&Nanda,S.(2011).Amoxicillin:Abroadspectrum.
International
JournalofPharmacyandPharmaceuticalSciences
,3(3),30
37.Retrievedfrom
http://www.ijppsjournal.com/Vol3Issue3/2249.pdf
[3]Lancashire,R.J.(2005).
Qualitativeanalysisoforganiccompounds.
Retrievedfrom
http://wwwchem.uwimona.edu.jm/lab_manuals/c10expt25.html
[4]McIntosh,James.(2015).
Amoxicillin:Whatisit?Whatdoesamoxicillintreat?
Retrieved
fromhttp://www.medicalnewstoday.com/articles/158481.php
[5]Ramos,F.,Boison,J.,&Friedlander,L.G.(2012).
Amoxicillin.
Retrievedfrom
ftp://ftp.fao.org/ag/agn/jecfa/vetdrug/122012amoxicillin.pdf
[6]UniversityofDelaware.(n.d.).
Identifyinganunknowncompoundbysolubility,functional
grouptestsandspectralanalysis
.Retrievedfrom
http://www.udel.edu/chem/CHEM322/Handouts/unknowns_lab_handout.pdf
[7]William,K.(n.d.).
Ethersandsulfidesfunctionalgrouptests
.Retrievedfrom
http://faculty.swosu.edu/william.kelly/pdf/qo9.pdf

NattanitTrakullapphan(Nam)

Determinethefunctionalgrouppresentintheseunknown:
(a)UnknownAissolubleinwaterandgivesbubbleswith5%NaHCO3.
=>
carboxylicacid
(b)UnknownBisinsolubleinwater,insolublein5%NaOH,butsolublein5%HCl.
=>
amide
(c)UnknownCisinsolubleinwater,insolublein5%NaOH,insolublein5%HCl,soluble
withacolorchangeinconc.H2SO4,anddecolorizesbothKMnO4(aq)andbrominein
cyclohexane.
=>
alkene
(d)UnknownDissolubleinwater,doesnotproducebubbleswith5%NaHCO3,givesa
precipitatewith2,4DNP,andgivesafuchsiacolorwiththeSchifftest.
=>
aldehyde