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InformationonPrelabAssignments
RecrystallizationandExtraction
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Chem 212PrelabLecture1
PrelabAssignments
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*READLabNotebookandPrelabAssignment postedonmyCourses*
REQUIREMENTS:
1. Name,date,experimenttitle,lab
partner(ifapplicable)
2. ReactionScheme
3. Literaturereferences(ifapplicable
USUALLYFORMSDSsheets)
4. Physicalconstantsandsafety
considerations(reagents/product)
5. Quantitiesofchemicalsusedand
theoreticalyieldofproduct
6. ProceduralFlowChart/Summaryand
Mechanism
Recrystallization(SoloExp#1)
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BACKGROUNDREADING:
Techniques WeightsandMeasure,Recrystallization,Filtration,MeltingPoint
TylenolSynthesis
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Analgesic
Antipyretic
Antiinflammatory
Analgesic
Antipyretic
PURE???
PURPOSE: synthesizeTylenol(acetaminophen)andpurifyit
PurityandProperties
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Thepurityofasampleaffectsitsphysicalproperties:
Solubility
Meltingpoint
Boilingpoint
Physiologicalresponses
Purityrequirements canbeupto99.999%!!
PURE???
Efficient/reliablemethodsforpurificationextremelyimportant!
PurificationTechniques
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Purificationtechniqueuseddependsonthenatureofthematerial:
SOLIDSRECRYSTALLIZATION,CHROMATOGRAPHY
Recrystallizationpurifiesbasedonvariablesolubility
propertiesofdesiredcompoundandimpurities
LIQUIDSDISTILLATION,CHROMATOGRAPHY
PURPOSE: synthesizeTylenol(acetaminophen)andpurifyit
byrecrystallizationfromwater
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Overview RecrystallizationLab
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TylenolSynthesis
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CRUDEYIELD(g)
StepsofRecrystallization
1SOLVENTSELECTION
IMPURITIES ALWAYSSOLUBLEorALWAYSINSOLUBLE
LOWBOILINGPOINT
NOCHEMICALREACTIONWITHDESIREDMATERIAL
COLD HOT
SOLUBLE
INSOLUBLE
YourdesiredcompoundshouldbeSHIC
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StepsofRecrystallization
2DISSOLUTION
addsmall amount of
recrystallizationsolvent
addmore HOT recrystallization
solvent until J UST dissolved
HEAT HEAT
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**MAKESURETOUSETHEMINIMUMAMOUNTOFSOLVENTPOSSIBLE!!**
StepsofRecrystallization
3 HOTFILTRATION(COLOURED IMPURITY)
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add small amount of
decolourizing charcoal
gravity filter - through filuted filter
paper - into clean, HOT flask
HOT SOLVENT +
DISSOLVED COMPOUND
INSOLUBLE CHARCOAL
heat again
(fewmin)
StepsofRecrystallization
3 HOTFILTRATION(INSOLUBLEIMPURITY)
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gravityfilter - through filutedfilter
paper - into clean, HOT flask
HOT SOLVENT +
DISSOLVEDCOMPOUND
INSOLUBLE IMPURITIES
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StepsofRecrystallization
4 CRYSTALFORMATION
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StepsofRecrystallization
5 FILTERING/DRYINGCRYSTALS
ICE COLDSOLUTION +
LOTS OF CRYSTALS
vacuumfilter - throughBuchner
funnel - into clean, vacuumflask
attach to vacuum
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PURIFIEDYIELD(g)
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StepsofRecrystallization
6 MASSAND%YIELD
CRUDE PURIFIED Theoretical
MASS 1.5 g 0.88g 3.0g
%YIELD(purified)=masspurified x100%=0.88g x100%=29%
theoretical 3.0g
%YIELD(crude)=masscrude x100%=1.5g x100%=50%
theoretical 3.0g
TOTALLYFICTICIOUSVALUES
StepsofRecrystallization
6 MASSAND%RECOVERY
CRUDE PURIFIED
MASS 1.5 g 0.88g
%RECOVERY=masspurified x100%=0.88g x100%=59%
masscrude 1.5g
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TOTALLYFICTICIOUSVALUES
StepsofRecrystallization
7 MELTINGPOINTANALYSIS
MELTINGPOINT
physicalpropertyofacompound,indexofpurity
fixedvaluereportedasaRANGE
CRUDE PURIFIED
MPVALUE depressed
close to
literature
MPRANGE
BROAD
(>3
o
C)
NARROW
(1 3
o
C)
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StepsofRecrystallization
7 MELTINGPOINTANALYSIS
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Extraction(GroupExp#1)
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BACKGROUNDREADING:
Techniques WeightsandMeasure,Reflux,Distillation,Filtration,MeltingPoint
NutmegandTrimyristin
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NaturalProducts:substance/chemicalderivedfrom
naturalplantoranimalsources
Examples: terpenes andcarotenoids,steroids,
lipids,alkaloids,carbohydrates,sugars,
proteins,aminoacids,andvitamins
PURPOSE: isolatealipid(trimyristin)fromitsnatural
source(nutmeg)
HOW???
Extraction
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Extraction:separationofamixturebasedonsolubilityproperties
Liquidliquid
extraction
Solidliquid
extraction
2immiscibleliquids
solid+liquid
*Isolationofanaturalproductfromitssourcematerialispossibletodo
byEXTRACTIONifthecomponentshavedifferentsolubilities
Lipids
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Lipids: waterinsoluble,organicmolecules
canbeextractedfromcells/tissueswithnonpolar,organicsolvents
(chloroform,ether,benzene,etc.)
Triglycerides: lipidsmadefromfattyacidsandglycerol
properties/characteristicsderivedfromthoseoffattyacidtail
Overview ExtractionLab
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GroundNutmeg IsolatedSolidTrimyristin
EXTRACTION
PURPOSE: isolatealipid(trimyristin)fromitsnaturalsource
(nutmeg)byextractionwithanonpolarorganicsolvent
1.ExtractingTrimyristin
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5gnutmeg
12ml ether
50ml roundbottomflask (RBF)
attachcondenser
water out
water in
reflux 40min
CLAMP
WARMWATER BATH
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2.CollectingCrudeTrimyristin
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water out
water in
cool suspension
gravity filtration
(keepfiltrate)
50ml Erlenmeyer
ETHER +TRIMYRISTIN
INSOLUBLE BITS OF NUTMEG
FILTRATE
2.CollectingCrudeTrimyristin
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CRUDEYIELD(g)
transfer filtrate
50ml pre-weighed RBF
attach distillation
apparatus
distill off ether
water out
water in
collection flask
remove distillation
apparatus when
ether removed
weigh flask
3.PurifyingTrimyristin
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4.CollectingPurifiedTrimyristin
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PURIFIEDYIELD(g)
ICE COLDSOLUTION +
WHITE SOLID
vacuumfilter - throughBuchner
funnel - into clean, vacuumflask
attachto vacuum
ACETONE +IMPURITIES
PURIFIEDSOLIDTRIMYRISTIN
%Yield
Nutmeg
CRUDE
Trimyristin
PURIFIED
Trimyristin
MASS 2g 1 g 0.6g
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%YIELD(crude)=masscrude x100%=1 g x100%=50%
massnutmeg 2g
%YIELD(purified)=masspurified x100%=0.6g x100%=30%
massnutmeg 2g
TOTALLYFICTICIOUSVALUES
%Recovery
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Nutmeg
CRUDE
Trimyristin
PURIFIED
Trimyristin
MASS 2g 1 g 0.6g
%RECOVERY=masspurified x100%=0.5g x100%=60%
masscrude 1g
TOTALLYFICTICIOUSVALUES
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MeltingPointAnalysis
MELTINGPOINT
physicalpropertyofacompound,indexofpurity
fixedvaluereportedasaRANGE
CRUDE PURIFIED
MPVALUE depressed
close to
literature
MPRANGE
BROAD
(>3
o
C)
NARROW
(1 3
o
C)
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MeltingPointAnalysis
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