TracyRompich

2/7/15
Chemistry
BriannaBalke

EsterSynthesisLabReport

Purpose
Thepurposeofthislabistolearntheprocessbywhichsweetsmellsaresynthesized.

Introduction
Inchemistry,therearesixfunctionalgroups,butthreemainones.Theyareesters,
carboxylicacids,amines,ketones,alkanes,andalcohols.Estersaresweet,carboxylicacidsare
putridsmelling,aminesarefishy,ketonesareminty,alkanesaregasolinesmelling,andalcohols
arealcoholsmelling.Themainonesarecarboxylicacidsandalcoholswhichformesters.
Molecularformulashelppredictamoleculessmellalongwiththechemicalnameandstructure.
Dependingontheamountofoxygenandwhereitsplacedinthestructureisthedifference
betweenanester,acarboxylicacid,mint,andalcohol.Fishysmells,ontheotherhand,will
alwayshavenitrogeninthemolecularformulaandstructure.But,chemicalnamesalsohelp
whenfiguringoutthesmell.Thechemicalnameofesterswillalwaysinvolvetylandatewhile
carboxylicacidswillendinacid.Amineswillendinamineandketonesinone.Then,theres
alkaneswhichwillendinaneandalcoholsinol.Unfortunately,namesdontalwayshelp
becauseanestercanhavethesameendingasacarboxylicacid,sostructureosalsoimportantto
findingasmell.

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
alcoholtoatesttubewith
glacialacetic
acidpremeasured.
2. Gentlyagitatethemixture.
3. Add1dropofconcentratedsulfuricacid(H
SO
).
2
4
4. Gentlyagitatethemixture.
5. Placethetesttubeinabeakerofhotwaterfor3minutes.
6. Add
20
dropsofwater.
7. Carefullysmellthemixture,andrecordthesmell.

Banana:
1. Add
6
dropsofalcoholtoacleantesttube.
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
octyl
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.

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
butyricacid
.
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
butyricacid
.
2. Add
6
dropsof
methyl
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.


Results:
REACTANTS

PRODUCT

FLAVOR

Alcohol

CarboxylicAcid

Ester

Intended

Observed

MethylAlcohol

SalicyclicAcid

MethylSalicylate

Wintergreen

Grape

Pear

Banana

Orange

Pineapple

Strawberry

Apple

AnalysisofResults
Wintergreen:

Orange:

Grape:

Pineapple:

Pear:

Strawberry:

Banana:

Apple:


Part2:Questions
Answerthequestionsbelow:

1. Whatevidencedoyouhavethatanesterwasproducedineachofyourreactions?

Becauseofthestructureandthesmell,Icansaythattheproductionsofmyreactions
wereesters.Mostofthemweresweetsmelling,whichisonewaytodefineanester.The
reactantswerealsoanalcoholandacarboxylicacidwhicharewhathelptoformanester.

2. Whatistheroleofsulfuricacidinthisreaction?Howcomeitisntlistedwiththeother
reactants?

Sulfuricacidisacatalyst,whichasubstanceusedtoaccelerateachemicalreaction.The
sulfuricacidhelpedproducetheesterfasterthanitwouldhavewithoutit.Itisntlistedasa
reactantbecausethechemicalreactionwouldstillworkwithoutit.Thechemicalreactionprocess
wouldjustbeslower.

3. Ifyouwantedtosynthesizeamoleculethathadthesweetsmellofcinnamon(pictured
below),whatwouldyoudo?Whatingredientswouldyoumix?(Drawthem.)What
reactionwouldtakeplace?

Iwouldmixanalcoholandacarboxylicacidbecausenormally,thosearewhatforman
ester.Thehydrogenfromthealcoholandtheoxygenandhydrogenwouldcometogethertoform
water,whiletherestofthetwosubstancescombinetoformtheester.\

qa
EthylCinnamate

Conclusion
Inyourownwords,
describe
whathappensata
molecularlevel
whenanestersynthesisreactiontakes
place.

Atmolecularlevel,twosubstancesarecombinedtoformanester.First,thehydrogenfroman
alcoholandtheoxygenandhydrogenfromacarboxylicacidjointogethertoformwater.Then,the

oxygenleftfromthealcohol,withtherestofitsstructure,combineswithwhatisleftofthecarboxylic
acidandtogether,formanester.