(CHE276)OrganicChemistryLaboratory

TheLaboratoryNotebook

TheLaboratoryNotebook

Your notebook will serve as a permanent record of your experimental work. It will contain the
informationyouneedtocompleteyourworkefficientlyandsafely,andyouwillusetheinformation
containedinyournotebooktowritelaboratoryreportsexplainingyourresults.Forthesereasons,itis
importantthatyournotebookbecompleteandaccurate.Asageneralrule,agoodnotebookisonefrom
whichsomeoneelsecanrepeatyourexperimentalworkinthesamewaythatyouhavedoneit.
I.GeneralGuidelines:
1.Yournotebookmustbebound,thepagesnumbered,andhaveacarboncopy.
2.Writeyourname,thecoursename,andsection#onthecoverorfrontpage.
3.Alwaysusepermanentink,notpencil.
4.WriteitdownNOW.Yournotebookisalogofwhatyoudoasyoudoit.
5.Usecompletesentences.
6. Write everything in your notebook. Weights, temperatures, everything! When recording
experimentaldata,alwaysincludeunits.
7.Donoterase!Ifyoumakeanerror,drawasinglelinethroughit,andcontinue.Theoriginal
statementshouldstillbelegible.
8.Neverremoveoriginalpagesfromyournotebook.Youmayremovecarboncopies.
9.Dateeverypageasyouuseit.
10.Writelegibly!Ifyournotebookisillegibleitwillnotbegraded.
II.TheNotebook:
Eachexperimentrecordedinyournotebookshouldcontainthesectionsoutlinedbelow.Acarbon
copyofyournotebookpageswillbecollectedattheendofeachlaboratoryperiodandwillgradedas
apartofyourlabreport.Latenotebookpageswillnotbeaccepted.
SectionsAEmustbecompletedbeforeyoubegintheexperiment.Thisistheprelab.YourTAwill
verifythatthissectioniscomplete. Youwillnotbeallowedtoproceedwiththeexperimentifyou
havenotcompletedtheprelab.
SectionF,theExperimental,isrecordedasyouproceedeachday.
Prelab:Completedbeforeyouarrive.
A.Title:
Givetheexperimentanaccurate,descriptivetitle.
B.Purpose:
Discussthegeneralpurposeoftheexperimentintwoorthreesentences.Iftheexperimentisa
synthesis (as opposed to a technique), write the chemical equation, including reagents and
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expectedproduct(s).Formultistepsyntheses,writeoneequationforeachtransformation,including
thepreparationofreagents.

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C.References:
Citethereferenceuponwhichyourexperimentalprocedureisbased.Inmostcasesthiswillbe
yourlaboratorymanualand/orasupplementalhandout.Alsocitethesource(s)oftheinformation
foundintheChemicalProperties&Safetytable(partD).
D.ChemicalProperties&Safety:
Makeatablethatliststhechemicalpropertiesofallreactants,reagents,andsolventsthatyouwill
beusingintheexperimentaswellasfortheproductsyouwillmake.Thistableshouldincludethe
nameofthecompound,MW,density,mp,bp,etc.Foreachcompound,alsolistthetoxicity(if
known),andanyotherimportantsafetyinformation(flammable,corrosive,irritant,etc.).Some
usefulreferencesareprovidedattheendofthishandout.Asampletableisshownbelow:
E.ResearchPlan:
Thissectionwillincludespecificinstructionsonhowtoperformthelab.Itmustbecomplete
before you arrive. In combination with the Experimental (Section F; completed during the
experiment),anyreadershouldbeabletorepeattheexperimentasyoudiditbasedonwhatyou
havewrittenhere.Topreparethissection:
Splitthenotebookpageinhalfvertically(thishasbeendoneforyouinthenotebooklisted
forthiscourse).
Brieflyoutlinetheprocedureyouwillfollowonthelefthandsideofthepage.Leavetheright
hand side blank. You will use it later to record procedural modifications, data, and
observationswhenyouactuallyperformtheexperiment(sectionF).
Youdonotneed tousecomplete sentences whenpreparing the researchplan, butyour
outlineshouldprovideenoughdetailthatyoucanworkdirectlyfromyournotebook,using
yourlabmanualonlyasareferenceforclarification.Includetheamountsofreagentsyou
expecttouse.Asappropriatealsorecordreagentpurityand/orconcentration.
Incorporateanychangesthatweremadeinthelablecture.
Use your own words. Do not copy directly from the text or handout (this constitutes
plagiarism!).
Iftherearemultiplepartstoanexperiment,youmustprovideanoutlineforeachpart.
Thisisalsotheplacetodrawanyspecializedlaboratorysetupsthatyouwilluse.
ExperimentalSection:Recordedasyouproceedeachday.
F.Experimental:
Thissectionofyournotebookiswrittenduringthecourseofalaboratoryperiod,andshouldbe
recorded on the right hand side of the pages that contain the Research Plan (section E). An
examplefollows.Thisportionofthenotebookisarecordofwhatyoudoasyoudoit.Youdonot
neadtorewritetheentireprocedure,butyouwillneedtonoteanydeviationsfromtheResearch
Plan.Recordyourdataandobservationscompletelyandaccurately.Theinformationincludedhere
may help you understand later if your experiment was successful, or what went wrong. This
sectionmustbecompletedbeforeyouleavethelabfortheday.
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Describeanychangestotheprocedurethatyoumakeduringthecourseoftheexperiment.
Recordtheactualamountofreactants,reagentsandsolventsthatyouuse.Includeunits.
Recordyourobservations.Includeanythoughtsyouhaveaboutwhatmaybegoingon.Note
anydifficultiesthatyouencounter.
Makesuretorecordanymeltingpoints,boilingpoints,weights,etc.beforeyouleavethelab
whetheryouthinkyouneedthemornot.Chancesarethatyouwill.DrawingsofTLCplates
shouldalsobeincludedhere.Besureyourdataisclearlylabelledsuchthatsomeoneelse
wouldbeabletofigureoutwhatitrepresents.
Dontforgettorecordthephysicalcharacteristicsofanycompoundsyouisolate(e.g.solid,
liquid,shapeofcrystals,color,etc.).Haspurificationresultedinanyphysicalchange?
Other things you might wish to record: the formation and identification of layers, the
evolutionofheatorgas,theformationandcharacteristics ofaprecipitate,reactiontime,
unknownnumberifapplicable,oryourpartnersname(ifany)formostexperimentsyou
willworkindependantly.
Attheendofeachdayinitialanddatewhatyouhavewritten.
SubmitacarboncopyofyournotebookpagestoyourTAbeforeyouleaveeachday.These
pages will be graded as part of your laboratory report (Appendix D). Late notebook
pageswillnotbeaccepted.
Belowisanexampleoftheresearchplan,withexperimentaldetails,data,andobservationsfilledinas
theywouldbeduringthelaboratoryperiod.
III.References:
Thefollowingreferenceswillbehelpfulasyoucompleteyourprelab.Youwillfindallofthese
sourcesinthereferencesection(room103)oftheScienceandTechnologyLibraryorontheweb.
Pleasefamiliarizeyourselfwiththemasyouwillusethemfrequentlythroughoutthesemester.
GeneralChemicalProperties&Safety:
1.AldrichCatalogofFineChemicals.

TP202.A43

2.CRCHandbookofChemistryandPhysics

QD65.H231

3.TheMerckIndex

RS356.M524

4.DictionaryofOrganicCompounds

QD251.D51996

5.Lange'sHandbookofChemistry

QD65.L362

6.HazardousChemicalsDeskReference

T55.3.H3L492002

7.Sax'sDangerousPropertiesofIndustrialMaterials

T55.3.H3L4942000

ResourcesontheWeb:
1.SIRIMSDSIndex*

http://hazard.com/msds/index.php
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2.SigmaAldrichHomePage

http://www.sigmaaldrich.com

3.Reaxys

www.reaxys.com(oncampusonly);citeprimarylit.

*TheMaterialsSafetyDataSheet(MSDS)isthebestsourceforsafetyinformation.Many
chemicalpropertiescanalsobefoundhere.
IV.SampleNotebookPage
EXP NUMBER EXPERIMENT/SUBJECT

DATE

37

9/15/10
LOCKER/DESKNO COURSE & SECTION NO.

NAME

Polly Ester

CHE 276, T 12:30pm (M004)

Synthesis of Isoborneol

Purpose: To synthesize isoborneol from camphor. To learn the technique of gas

chromatography and use it to evaluate the ratio of reduction products.

Na BH 4
CH 3 OH

OH

H
OH

References: CHE 276 Organic Chemistry Lab Manual, 2007, pg 52.

SIRI MSDS Index
http://hazard.com/msds/index.php
Properties & Safety:
compound
camphor
NaBH4

MW
(g/mol)
152.24
37.8

mp
(C)
179-180
---

bp
(C)
-----

density
(g/mL)
-----

methanol
ethyl ether
isoborneol

32
74
154.25

----212-214

64
35
---

miscible
0.71
---

safety
harmful if swallowed
severe irritant, may cause
burns, keep away frm water
toxic
flammable
flammable, irritant

Research Plan

Experimental

1. Obtain about 0.1g of camphor

camphor used: 0.106g (white solid)

2. Combine with 0.5mL methanol in a small

test tube

used ethanol as solvent instead of methanol

NaBH4 used: 0.059g 0.064g

3. Add 0.060g sodium borohydride in

portions

some gas evolution observed (bubbles)

4. warm to reflux in a sand bath; heat 2 min

5. Analyze reaction mixture by TLC. Develop
plate in 25% ethyl acetate in hexanes;
vizualize with iodine.

4cm

3.5cm
2.2cm
C I

C = ca mphor
I = i sobor n eol
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