CassidyTitchenell

February22,2016
Chemistry
BriannaBalke

EsterSynthesisLabReport

Purpose:

Thepurposeofthislabistolearntheprocessbywhichsweetsmellsaresynthesized.

Introduction:

Everythingintheworldhasasmell,(somemoredistinctthanothers),whicharecreatedbymolecules.
Scientistshavetheabilitytoidentifyandpredictthesmellofsomethingbasedonamoleculesformula,name,
andstructure.Byexaminingtheatomsandthestructureofamolecule,oneisabletopredicthowsomethingis
goingtosmell.Thisisknownasafunctionalgroup.Afunctionalgroupisapuzzlepiecethatallowsoneto
identifyamoleculewithoutsmellingitsincethereisaconsistentstructuralpieceineachmoleculeofthatsmell.
Forexample,ifamoleculesformulanameendsinateandcontainsanester(twooxygenatomswhereoneis
doublebondedtoacarbonatom),thenitisgoingtohaveasweetsmell.Ifamoleculesnameendsinmine
anditcontainsanitrogenatom,itisgoingtobeanamineatomandwillhaveafishysmell.Throughoutthe
estersynthesislab,avarietyofsmells,suchaspearandbanana,wereartificiallycreatedbycombining
carboxylicacidswithalcoholsandsulfuricacidinalab.

FunctionalGroups

Smell

FunctionalGroup
Name

IdentifyingFunctional
GroupStructure

IdentifyingFormula
Name

Sweetsmells

Ester

CO

endsinate

Mintysmells

Ketone

CCC

endsinone

Fishysmells

Amine

N(nitrogenatom)

endsinmine

Putridsmells

Carboxylicacid

COH

endsinlicandacid

Gasolinesmells

Alkane

nooxygen

endsinanes

Alcoholsmells

Alcohol

OH(oxygenand
hydrogen)

endsinol

Procedure:

Wintergreen:
1. Add
6
dropsof
methyl
alcoholtothetesttubethathas
salicylic
acidpremeasured.
2. Gentlyagitatethemixture.
3. Add1dropofconcentratedsulfuricacid(H
SO
).
2
4
4. Gentlyagitatethemixture.
5. Placethetesttubeinabeakerofhotwaterfor3minutes.
6. Add
15
dropsofwater.
7. Carefullysmellthemixture,andrecordthesmell.

Grape:
1. Add
6
dropsof
methyl
alcoholtothetesttubethathas
anthranilic
acidpremeasured.
2. Gentlyagitatethemixture.
3. Add1dropofconcentratedsulfuricacid(H
SO
).
2
4
4. Gentlyagitatethemixture.
5. Placethetesttubeinabeakerofhotwaterfor3minutes.
6. Add
15
dropsofwater.
7. Carefullysmellthemixture,andrecordthesmell.

Pear:
1. Add
6
dropsof
npropyl
alcoholtoacleantesttube.
2. Add
6
dropsof
glacialacetic
acid.
3. Gentlyagitatethemixture.
4. Add1dropofconcentratedsulfuricacid(H
SO
).
2
4
5. Gentlyagitatethemixture.
6. Placethetesttubeinabeakerofhotwaterfor3minutes.
7. Add
20
dropsofwater.
8. Carefullysmellthemixture,andrecordthesmell.

Banana:
1. Add
6
dropsof
isoamyl
alcoholtoacleantesttube.
2. Add
6
dropsof
glacialacetic
acid.
3. Gentlyagitatethemixture.
4. Add1dropofconcentratedsulfuricacid(H
SO
).
2
4
5. Gentlyagitatethemixture.
6. Placethetesttubeinabeakerofhotwaterfor3minutes.
7. Add
20
dropsofwater.
8. Carefullysmellthemixture,andrecordthesmell.

Orange:
1. Add
6
dropsof
octylacetic
alcoholtoacleantesttube.
2. Add
6
dropsofglacialacid.
3. Gentlyagitatethemixture.
4. Add1dropofconcentratedsulfuricacid(H
SO
).
2
4
5. Gentlyagitatethemixture.
6. Placethetesttubeinabeakerofhotwaterfor3minutes.
7. Add
20
dropsofwater.
8. Carefullysmellthemixture,andrecordthesmell.

Pineapple:
1. Add
6
dropsof
nbutyl
alcoholtoacleantesttube.
2. Add
6
dropsof
butyric
acid.
3. Gentlyagitatethemixture.
4. Add1dropofconcentratedsulfuricacid(H
SO
).
2
4
5. Gentlyagitatethemixture.
6. Placethetesttubeinabeakerofhotwaterfor3minutes.
7. Add
20
dropsofwater.
8. Carefullysmellthemixture,andrecordthesmell.

Strawberry:
1. Thisreactionmusttakeplaceinafumehoodbecauseitusesasmellycompoundcalled
.
2. Add
6
dropsof
ethyl
alcoholtoacleantesttube.
3. Add
6
dropsof
butyric
acid.
4. Gentlyagitatethemixture.
5. Add1dropofconcentratedsulfuricacid(H
SO
).
2
4
6. Gentlyagitatethemixture.
7. Placethetesttubeinabeakerofhotwaterfor3minutes.
8. Add
20
dropsofwater.
9. Carefullysmellthemixture,andrecordthesmell.

Apple:
1. Thisreactionmusttakeplaceinafumehoodbecauseitusesasmellycompoundcalled
.
2. Add
6
dropsof
butyric
alcoholtoacleantesttube.
3. Add
6
dropsof
methyl
acid.
4. Gentlyagitatethemixture.
5. Add1dropofconcentratedsulfuricacid(H
SO
).
2
4
6. Gentlyagitatethemixture.
7. Placethetesttubeinabeakerofhotwaterfor3minutes.
8. Add
20
dropsofwater.

9. Carefullysmellthemixture,andrecordthesmell.

Results:

AnalysisofResults:

Part1:
Reactions

Part2:
Questions

1.
Anesterwasproducedineachofthereactionswhenthereactants,thealcoholandthecarboxylic
acids,combined.Oneisabletophysicallyidentifywhentheyhavesuccessfullycreatedanesterifthey
cansmellasweetsmellingsubstance,suchasstrawberriesorbanana.Asthealcoholandthecarboxylic
acidswerecombinedineachreaction,therewasahydrogenatomtakenfromthealcoholtocombine
withahydrogenatomandanoxygenatomtakenfromfromthecarboxlyicacidtocreatewater.The
remainingatomsinthealcoholandcarboxylicacidcombinedtoformthesecondproduct,anester.

2.
Theroleofsulfuricacidinthisreactionwastobethecatalyst.Sulfuricacidwasthesubstancein
thereactionthatacceleratedthechemicalreaction.Sinceitwasnotareactant,itwasnotlistedwiththe
otherreactantssinceitwasnotusedupinthereactionanddidnotaltertheotherchemicals.

3.


Ifonewantedtosynthesizeamoleculethathadthesweetsmellof
cinnamon,onewouldhavetomixcinnamicacidwithethylalcoholtocreateethylcinnamate.Duringthe
esterficationofcinnamicacid,thereactantswillbeethylalcoholandcinnamicacid.Asthereactantsare
combining,usingsulfuricacidasthecatalyst,onehydrogenatomfromtheethylalcoholiscombined
withahydrogenatomandanoxygenatomfromthecinnamicacidtocreatewater.Theremainingatoms
arethencombinedtocreateethylcinnamate,theester.Thereactionthatoccursinthislabisester
synthesis.

Thetworeactants,cinnamicacidandethylalcohol,arecombinedbythecatalyst,sulfuricacid,creating
twoproducts:waterandethylcinnamate.

Conclusion:

Whenanestersynthesisreactionoccurs,onehydrogenatomistakenfromthealcoholandcombined
withahydrogenatomandanoxygenatomfromthecarboxylicacid.Thethreeatomsarethencombinedto
createoneoftheproducts,water.Theremainingatomsofthealcoholandcarboxylicacidarethencombinedto
createanester.Overall,thetworeactantsinanestersynethsislab,alcoholandcarboxylicacid,arecombinedby
thecatalyst,sulfuricacid,tocreatethetwoproductsanesterandwater.

Appendix:SkeletalStructuresforAlcoholsandCarboxylicAcidsUsedinthisLab

Alcohol

CarboxylicAcid

Methyl

SalicylicAcid

nPropyl

AnthranilicAcid

Isoamyl

Octyl

nButyl

AceticAcid

Ethyl

ButyricAcid

5
ExceedsStandard

4
MeetsStandard

3
ApproachesStandard

1
BelowStandard

Introduction

Yourintroduction
intelligentlyand
thoroughlydiscusses
relevantbackground
information.

Yourintroduction
discussesrelevant
background
information,butmay
lacksomedetail.

Yourintroduction
outlinessomeof
relevantbackground
information,butis
lackingindetailand/or
containserrorsor
misunderstandings
aboutthelaborthe
content.

Yourintroductionlacks
significantdetail,
and/orcontains
substantialerrorsor
misunderstandings.

Procedure

Theprocedurehasbeen
correctlyfilledin.

Theprocedurehasbeen
filledin,andcontains
oneortwoerrors.

Theprocedurehasbeen
filledinandhasthree
orfourerrors.

Theprocedurehasbeen
filledin,butcontains
morethanfourerrors.

TableandReactions
(x2)

Allofyourchemical
reactionsarewritten
outcorrectly,including
catalysts.

Allofyourchemical
reactionsarewritten
outcorrectly.There
maybeoneerror.

Yourchemical
reactionsarewritten
out,butthereareafew
errors.

Yourchemical
reactionsare
substantially
incompleteorincorrect.

Scienceconcepts
(x2)

Yourdiscussion
questionsand
conclusionindicatethat
youhavemasteredthe
conceptsrelevanttothe
lab.

Yourdiscussion
questionsand
conclusionindicatethat
youhaveunderstood
mostoftheconcepts
relevanttothelab.

Yourdiscussion
questionsand
conclusionindicatethat
youunderstoodsome
theconceptsrelevantto
thelab.

Yourdiscussion
questionsand
conclusiondonotyet
showthatyou
understandtheconcepts
relevanttothelab.

Writing

Labisexceptionally
wellwritten.Thereare
almostnospellingand
grammarerrors,andthe
languageusedis
appropriate.

Labiswellwritten.
Thereareafewspelling
andgrammarerrors,but
theydonotdistractthe
reader.

Thereareanumberof
Thespellingand
spellingandgrammar
grammarerrorsarea
errorsthatyoushould
significantdistraction.
becapableofcorrecting
onyourown.

Total:

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