5 EXPERIMENT FROMCOFFEE EXTRACTION OF CAFFEINE chocolate, tea, soft drinks, and is foundin coffee, substance is a verycommon Caffeine Caffeine

from naturalsources. pills.It canbe synthesized or isolated and "stay-awake" and is alsofoundin colanutsandcacao 4o/o of tea and coffeeleaves, approximately constitutes beans.

Thus, of the methylxanthines. a member and,morespecifically, is an alkaloid, Caffeine \ \ of form the takes Pure Caffeine and theobromine. related to theophylline is closely Caffeine pointof it hasa melting whichcanbe brokenintoa soft powder. white,hexagonaicrystals, oC, and in Chloroform g/mol. soluble is it easily wdghtof 194.19 235"C 238 anda nrolecular 1H1,3,7-trimethyl"3,7dihydroname hasthe chemical partially in water. C-affeine soluble fromtea is a of Caffeine Theisolation formula CeHrollqOz. purine-'2,6dione" andthe molecular chemical advanced rather of number a use of whichin fact makes e<periment, simple*eeming the separate to chemically necessary is it tea, in a sample of processes. To isolate the Caffeine process extraction. known as is prior This to evaporation. taffeinefrom the restof the tea fromthe restof of a solution component a specific method of separa'ring is a chemical Extraction is verysoluble, isolated be to substance which the in This is doneby usinga solvent the solution. is notassoluble. whilethe restof the solution Caffeine because as the solvent was chosen hexane of this experiment, Forthe purposes in the Caffeine the is used, funnel when the separatory Thus, in this suffiance. is verysoluble times is three This done tre discardecl. can tea rest of the the into hexane and the tea dissolves by two This is followed tea is minimized. left in the discarded so that the amountof Caffeine Hydroxide Sodium the that is it believed water. with Hydroxide and one with Sodium washings more to be isolated the Caffeine allowing hason Caffeine, Chloroform weakens the attraction lateron. easily of a and purification isolation for the separation, is a widelyusedtechnique Extraction purification is used but a final methodof in a mixture.It is not, however, singlecomponent is the liquidextraction The mostcomrnon from its impurities. one subsbnce mainlyin separating whenthe solvelt, to another from one solvent of a substance liquidtype.It involves the transfer two solvents are immiscible. means or through eitherthroughsynthetic are obtained compounds Whensolidorganic pure. fractional Distillation, they are usuallynot isolation materials, from naturaliyoccurring purifying technique. freezing, are possible and recrystallization sublimation in a hot solventand of the impurecompound whichis the dissolving Recrystallization, general for technique form, is the only in a purer crystalline then allowingit to precipitate in the soluble or completely purifying are eitherinsoluble the impurities In this process, sollds. This situationmeansone recrystallization anci in all proportions. solventat all temperatures givesvery purematerial. recrystallization

Separatory Funnel Objectives: (1) To introduce and usethe simple extraciion technique to obtaincaffeine from tea. (2) To purify the caffeine withthe useof the sublimation method. Materials / Reagents Beakers / flaskalstirrers funnel/ watchglass Separatory Filterpaper / funnel Procedure
A. Extraction
I.

commercialtea hexane/ethanol NaOH

cheeses cloth NazSO+

2. 3.
4. 5. 6. 7.

Weighaboutfive (5) bagsof tea. Wrapthe tea leaves with the cheese cloth,placeit into a beaker containing about100 mLof distilled water. Heatthe mixture, whilecovered, until it boils, it to boilfor an extra5 minutes. allowing Let mixtureto cool in ice water and filter the boiledmixturewith the use of the cheese cloth. Transfer the extractinto a sepantoryfunnel. Add 60 mL of hexane/ethanol mixture,in 20-mLportions,to extractthe caffeine.Later, the solvent layers are thencombined and washed with 20 mL of 6 M NaOH. Oncemorewith a separatory funnel,the combined layea is pouredinto a beaker solvent linedwith anhydrous NazSOq. Letthe mixture for sbnd about5 minutes. pourout the "dried"extractinto an evaporating Carefully dish. Heatover a water bath untildryness. Cool andweigh.

B . Sublimation 1 . Coverthe evaporating dish (step 7. PartA) a pre-weighed watchglass.Place a damp glass. clothon the watch 2 . Heatthesystem untiltheunderside of the watchglass fogged becomes up. 3 . Carefully glass separate watch the fromthe evaporating dish. 't. Allow thedishto coolandweiqh thesublimate.

rof l
N TESTS CHARACTERIZATIO for the HYDR@ARBONS Thehydrocarbonfami|yisusua||yobseruedthroughtheco||apseofdoub|ebondsorthrough its manyreagents' towards mosthydrocarboni.i"gun",.lly unreactive Since reactions. addition simpler' is much chemicalanalysis To be able to Objective: (1)prepareschematicprocedureintheana|laisofthe.hydrocarbons rrndars.natichydrocarbcns the aliphatic oetween izi bistinguisn group (3) identify the hydrocarbot Materials / Reagents Test tubes/ test tube rack BeaLers / flasK DroPpers / stining rods cYlinders Graduated burner Hot Plate/ Bunsen Procedure
Test Solution Bromine Baeye/s hexane cvclohexeneethyne benzene nitrobenzerie Br2in CHzClz 5o/o 2o/o aQKMnO4 HzSOr / HNQ 10 o/oaq NSH

samPles Hydrocarbon

Iqniuon
Niti'ation BasicKMrOr

A. BromineTest

L{"$
B.

C. D.

E&.

and the mixture gendy sh9k9 sotution, to 5 d of thetes't Bh ir' CH2CI2 Add10d of 5olo is seen' uniildecoloriation the reagent adding tne ioroidringe.Cqrtinue observe Baeye/sAlfl the mixturead shake vigorously to 5 d cf thetest srrlution, l(Mnoc d of 2o/oaq ' notethe colorchange TestforUnsatuntirn Ignition dishandignitewitha glass / ewporirting plae 2 d of thetestsoiution ona watclr the propertieof theflanreprodued' match:Observe NitntionTest If novisible the mixture. shake b ,t d of thetestsolution. HNos Adrtg c cf Hzsoc/ andwarmin water of d 20 with the mixture Oilute withinaminute, is observed reactlon tie results' down waterbath-Note (Oxidation) ^ KMnOq Basic A d d S o fZ o /o a q K Mnoland3ofl0o/oaQNaoHto4dofthetestsoluti on.W ar m the tie changes. andobserue in w#r uatnior 2 minutes mixture

OuTtof"uise

the analysis'of thequalitative that willshow or flowchart diagram a schematic families. hYdrocarbon 2.Supplybalancedchemica|equationthatwi||repreentaposiUvetestforthetestsolutionsan gents' rea rmatory confi r respective thei

EXPERIMENT 8 CHARACTERIZATION TESTS for the - CONTAINING OXYGEN COMPOUNDS - alcohols, Thereare a number of oxygen<ontaining families ethers, aldehydes, ketones, carboxylic acids.Spectroscopy canreadily distinguish thesefamilies, but thereis no single chemical test to differentiate onefromtheother.The reactivity of thesecemprcuMs cccurs at the polarbonds. There are, however,specific confirmatory teststo identifythesecompounds. d Objectives: To be ableto (1) observe the physical result of eachtest. (2) relatethe physical results groups. to the functional Materials / Reagents Test tubes / test tube rack Droppers / stiners Graduated rylinder Hot plate Procedure A. Dichromate Test To 3 dropsof the test solution(b), add 2 dropsof 10 o/o KzCr$ and 5 dropsof 6 M HzSOq. Observe anycolorchange. , B. DNpHTest To 2 dropsof the ts add 1 mLof 95o/o ethanol,and 20 dropsof DNPH. Notethe olor of the precipitate that forms,If a the precipitate doesnot appearafter 15 minutes, heat in water bath for 15 minutes more. C. Tollen'sReagent To 5 dropsof tle ts add2 mLof the Tollen'sreagent. Record observation after 5 minutes.If no visiblechange is obserued, warmin water bathfor5 minutes. D. IodoformTest To 5 dropsof the ts add20 dropsof 10o/o KI. Thenslowlyadd20 d of 5o/o NaCCI.Warm in water bath.Observe anychange In appearance and odor. E. Fehling's Test To 5 dropsof the ts adda mixture of 10 dropsof Fehling's A and10 dropsof Fehling's B. Warmin waterbathuntilchanges areobserved. F. LucasTest To 5 drops ofthe ts add15drops ofconcentrated HCI anda pinch ofanhydrous ZnCl2. Shake the mixture untilan insoluble layeror emulsion forms.Notethe timefactor.If no change is observed, warmin waterbathuntilthe formation of turbidiU. 6 M H2SO4 10 o/o KzCr.Ft 2,4 DNpl=l Tollen's reagent 10olo KI anhydrous ZnCl2 NaCIO 5olo 95% ethanol Fehling,s A and B concd HCI

Observation
Sample/Test Ethanol Didrrcmate DNPH Tollen's Iodoform tuhlinot Lucas

1o butvl

2'butyl 3obutyl Acetone Acebohenone Butvraldehyde Formaldehyde Eenzaldehvde

*:Ff5 = test solution

Guide Questions Tabulatethe answers for the questions below: 1. The chemical composition of the reagents testsusedin the aboveprocedure. / confirmatory 2. Whichoxygen<ontaining familydoeseachreagent identiff? test positively / confirmatory 3. Whatphysical changes in question areobserved nc.2? 4. Supply the complete chemical equation that will represent change(s) in no.3. the physical Chemical Comoositbn
Ethanol

Confirmatory Test

Phpical Chanoe

Chemical Eouation

1" buM 2" but)4 3'bu$

Acebne Acebphenone Butyraldehyde

FormaHefryde
Benzaldefryde