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English Learning

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* Formål * Formålet med dette forsøg er, at bestemme identiteten af en ukendt alkohol, ud fra nogle parametre, og ved brug af udelukkelsesmetoden.

* Teori * Til rådighed er der fem nummereret flasker, med en alkohol i hver. I nedenstående skema er alkoholerne, samt informationer om disse, skrevet ind. Alkohol | Type | Strukturformel | Densitet | Kogepunkt | Ethanol | Primær alkohol | CH3 – CH2 – OH | 0,789 g/mL | 78,29° C | Propan-2-ol | Sekundær alkohol | CH3 – CH – CH3 OH | 0,780925 g/mL | 82,30° C | Butan-1-ol | Primær alkohol | OH − CH2 – CH2 – CH2 – CH3 | 0,8095 g/mL | 117,73° C | Butan-2-ol | Sekundær alkohol | CH3 – CH – CH2 – CH3 OH | 0,8063 g/mL | 99,51° C | 2-methylpropan-1-ol | Primær alkohol | OH – CH2 – CH – CH3 CH3 | 0,8018 g/mL | 107,89° C |

* Den flaske man vælger, indeholder en ukendt alkohol som har visse egenskaber. De egenskaber der skal bestemme identiteten af alkoholen er: a) Densitet (g/mL). b) Kogepunkt (° C). c) Alkoholens evne til at blive oxideret af Beckmanns blanding:
Beckmanns blandingen består af kaliumdichromat i svovlsur opløsning og er god til oxidationer af primære og sekundære alkoholer. Hvis der havde været en tertiær alkohol blandt de udvalgte alkoholer, ville denne ikke kunne oxideres af Beckmanns blanding og der ville da, ikke kunne ses nogen farveændring. Dette skyldes at tertiære alkoholer ikke kan oxideres, fordi det carbon-atom der er bundet til hydroxid-gruppen, ikke har nogen H+ at give væk. Fx 2-methylpropan-2-ol:
CH3

CH3

CH3 – C – OH

Ved redoxreaktionen, er kaliumionen K+ fra Beckmanns blandingen, en tilskuerion, mens den orange dichromation Cr2O72− indgår i reaktionen, hvor den reduceres til den grønne chrom(III)ion.
Nedenstående reaktionsskemaer er eksempler på oxidation af henholdsvis en primær- og en sekundær alkohol. 1) Ved oxidation af en primær alkohol fås en aldehyd (fx):
8H+ + 3C2H5CH2OH + Cr2O72− 3C2H5CHO + 2Cr3+ + 7H2O

2) Ved oxidation af en sekundær alkohol fås en keton (fx):
8H+ + 3CH3CHOHCH3 + Cr2O72− 3CH3COCH3 + 2Cr3+ + 7H2O

d) Oxidationsproduktets reducerende egenskaber:
Efter oxidationen bruges Fehlings væske, der er en basisk opløsning indeholdende kobber(II)ioner bundet komplekst til tartrationer.
Hvis oxidationsproduktet er en aldehyd, kan denne oxideres yderligere til en carboxylsyre og det vil da vise sig som et rødt bundfald ad kobber(I)oxid Cu2O. Dette skyldes at aldehydet er i stand til, at reducere kobber(II)ionerne til kobber(I)ioner, hvorimod en keton ikke kan og der vil i sådanne tilfælde, ikke dannes et rødt bundfald.
Fehlings væske kan altså bruges til at undersøge, hvilket oxidationsprodukt der kan være tale om og derved indsnævre mulighederne, for hvilken ’ukendt’ alkohol man startede ud med.
Et eksempel på en reaktion mellem kobber(II)ioner og en aldehydgruppe er som følger:
5OH− + R−CHO + 2Cu2+ R−COO− + Cu2O + 3H2O

e) Gaschromatografisk analyse:
Gaschromatografi virker ved at en prøve bringes på gasform, hvilken derefter føres med en inaktiv gas, bæregassen (i dette tilfælde, atmosfærisk luft), gennem en kolonne. Kolonnen, der er opbygget af et inaktivt pulver, der er dækket af en organisk væske med et højt kogepunkt, udgør gaschromatografens stationære fase. Bæregassen (den mobile fase) fører prøven gennem den stationære fase, hvoraf nogle af prøvens bestanddele bindes bedre til den stationære fase, mens andre elementer forbliver i den mobile fase. På denne måde vil gaschromatografens detektor, registrere de enkelte komponenter af prøven, på forskellige tidspunkter og man kan da sammenligne chromatogram for prøven, med chromatogram for et rent stof og kvalitativt bestemme, hvad ens prøve består af.

* Apparatur * Stativ. * Trefod med trådnet. * Bunsenbrænder. * 100 mL rundbundet kolbe med slib. * Destillations apparatur med slib. * 10,0 mL fuldpipette med pipettebold. * 2 små bægerglas. * 2 reagensglas i stativ. * 2 vandbade (er varmt og et koldt). * Termometer.

* Kemikalier * Den valgte, ukendte alkohol med nummeret 4. * Beckmanns opløsning. * Fehlings I og Fehlings II (Blanding af lige store mængder af disse, udgør Fehlings væske).

* Udførelse 1) Densitetsbestemmelse:
Et bægerglas placeres på vægten, hvorefter vægten nulstilles.
Derefter tilsættes 10,0 mL alkohol, med fuldpipette, til bægerglasset.
Alkoholens masse noteres ned.

2) Kogepunktsbestemmelse:
(Beskyttelsesbriller benyttes under destilleringen!)
De 10,0 mL alkohol hældes fra bægerglasset over i en 100 mL rundbundet kolbe med slib.
Destillationsapparaturet sættes op som vist nedenfor.
Koldt vand udløb
Koldt vand indløb

En slange sættes fast på vandhanen og på indløbet og en anden slange føres fra udløbet og ud i vasken.
Bunsenbrænderen tændes og alkoholen i den rundbundede kolbe bringes lige akkurat i kog.
Når temperaturen af alkoholens dampe har været konstant i noget tid, aflæses alkoholens kogepunkt.
Denne konstante temperatur (kogepunktet), noteres ned.

3) Oxidation med Beckmanns blanding:
(Beskyttelsesbriller benyttes!)
Den destillerede alkohol hældes fra bægerglasset tilbage i destillationskolben, på nær den smule, der senere bruges til gaschromatografisk analyse.
Destillationskolben køles i et koldt vandbad.
Der tilsættes forsigtigt 20,0 mL Beckmanns blanding (blanding af kaliumdichromat og svovlsyre), af læreren.
Det markante farveskift noteres ned.
Straks efter tilsætningen, destilleres ca. 2 mL over i et rent bægerglas og oxidationsproduktets kogepunkt noteres ned som før.
Den resterende grønne chrom(III)-opløsning, hældes i den røde affaldsbeholder med mærket ”Uorganisk affald – surt”.

4) Undersøgelse af oxidationsproduktets reducerende egenskaber:
(Beskyttelsesbriller benyttes!)
Vha. engangspipetter, overføres 1 mL Fehling I og 1 mL Fehling II over i et reagensglas.
Derefter tilsættes 1 mL af oxidationsproduktet, til reagensglasset indeholdende Fehlings væsken.
Reagensglasset anbringes i et 200 mL bægerglas der er halvt fyldt med vand, hvilken placeres på en trefod med trådnet.
Vandet bringes i kog med en bunsenbrænder og efter 2-3 minutter, konstateres der om der har fundet en reaktion sted (ses som rødt bundfald).
Hvis Fehlings prøven er positiv, fjernes det røde bundfald med koncentreret saltsyre (HCl).
Resultatet noteres ned.

5) Gaschromatografisk analyse:
Gaschromatografi af destillatet i bægerglasset, køres sammen med læreren og prøvens retentionstid (den tid, et bestemt stof tager om at passere gennem gaschromatografen) sammenlignes med retentionstider for de opgivne alkoholer.

* Resultatbehandling * I nedenstående skema er forsøget data skrevet ind og behandlet. Undersøgelse | Farve | Data | Udregning og resultat | Densitet | ------------------------------------------------- | 10,0 mL vejede 7,995 g. | ρ= 7,995 g.10,0 mL=0,7995 g/mL | Kogepunkt | ------------------------------------------------- | 97° - 98° C | tk = 97° - 98° C | *Oxidation.(Beckmanns blanding) | Klar + Orange Grøn | ------------------------------------------------- | ------------------------------------------------- | **Fehlings prøve | Klar øverst, kongeblå nederst | Oxidationsproduktet kan ikke oxideres yderligere. | Ingen reaktion (ingen bundfald) = Oxidationsproduktet er ikke en aldehyd, men en keton. | Gaschromatografi | ------------------------------------------------- | Destillatets chromatogram viser at retentionstiden er lidt over to min. | Ved Fehlings prøven bestemte vi at oxidationsproduktet var en keton, og idet de eneste stoffer med lignende retentionstider er primære alkoholer, må vores udgangspunkt have været den sekundære alkohol butan-2-ol. | * Da densiteten blev bestemt, var det ikke muligt at udelukke nogen stoffer definitivt, idet det var en relativ usikker målemetode. Dog var der sandsynligvis ikke tale om propan-2-ol eller butan-1-ol, da disses densiteter er de to, mest forskellig fra den bestemte. * Den næste undersøgelse vi foretog, var kogepunktsbestemmelse, hvilket indsnævrede mulighederne for hvilken alkohol vi undersøgte.
Idet kogepunktet blev bestemt til 97°-98° C., kan vi udelukke at der er tale om ethanol, propan-2-ol og butan-1-ol, fordi deres kogepunkter er for forskellige fra det fundne. * *Ved oxidationen med Beckmanns blanding, der er orange, gik alkoholen fra at være klar til at være meget mørke grøn. Dette skyldes, som nævnt tidligere, at den orange dichromation reduceres til den grønne chrom(III)ion, af alkoholen der samtidigt oxideres.
Hvis det var en primær alkohol, ville oxidationsproduktet være et aldehyd og ved tilsætningen af Fehlings væske, ville aldehydet blive oxideret til en carboxylsyre.
Hvis der derimod var tale om en sekundær alkohol, ville oxidationsproduktet være en keton, hvilken ikke ville kunne oxideres yderligere, ved tilsætningen af Fehlings væske. * **Da oxidationsproduktet blev tilsat Fehlings væske, delte reagensglassets indhold sig i to faser: Den øverste del var klar og farveløs, modsat den nederste der var kongeblå.
Der blev ikke dannet rødt bundfald ved opvarmning, hvilket betyder at Fehlings prøven var negativ, og at oxidationsproduktet ikke var et aldehyd, men en keton. Vi kunne derfor konstatere at vi ikke havde en primær alkohol som udgangspunkt, hvilket medførte at vi kunne udelukke 2-methylpropan-1-ol. og at det altså var butan-2-ol (resten havde vi udelukket tidligere) i flaske nr. 4. Butan-2-ol O2 Butan-2-on
CH3 – C – CH2 – CH3 O
CH3 – CH – CH2 – CH3 OH

Oxidationen ser således ud: , , , , ,

* Ved sammenligningen af chromatogrammer for de fem udvalgte alkoholer og den valgte alkohol, kan man altså få bekræftet om det er den korrekte identitet, man har fastslået som værende den valgte alkohol.
Nedenunder ses chromatogrammerne for de fem alkoholer, samt chromatogrammet for alkoholen i flaske 4 (den valgte).

Som det ses af sidste sides chromatogram, havde vores prøve en retentionstid på lidt over to min.. Kun ethanol og 2-methylpropan-1-ol havde relativt lignende retentionstider, og da vi udelukkede dem ved de tidligere undersøgelser, blev det bekræftet, at den valgte alkohol var butan-2-ol.

* Fejlkilder
I dette forsøg, består de mulige fejlkilder i: * Unøjagtigheder ved afvejning af alkoholen (densitetsbestemmelse).
Vægten er meget følsom og derfor kan der forekomme mindre afvigelser i alkoholens masse og derved også afvigelser for densiteten. * Upræcis aflæsning af kogepunktstemperaturen.
Hvis destilleringen udføres med ujævnheder, dvs. at opvarmningen ikke er konstant, svinger temperaturen nogle få grader C. og da kan den aflæste temperatur medføre, at man drager konklusioner på baggrund af ukorrekte data. * Observering af rødt bundfald ved tilsætningen af Fehlings væsken.
Det kan være vanskeligt at detektere det røde bundfald, idet der nogle gange er uhyrlig lidt. * Konklusion * Konklusionen på forsøget er, at det er lykkedes os at bestemme identiteten af vores alkohol (flaske nr. 4) til butan-2-ol, vha. tre undersøgelser: a) Densitetsbestemmelse: 0,7995 g/mL. b) CH3 – C – CH2 – CH3 O
Kogepunktsbestemmelse: 97° − 98° C. c) Oxidationen med Beckmanns blanding, dannede ketonen butan-2-on:

d) Vores Fehlings prøve var negativ, hvilket betød at vores oxidationsprodukt ikke kunne have været et aldehyd og derfor kunne vores alkohol ikke have været en primær alkohol. Sammen med densitets- og kogepunktsbestemmelsen, bestemte vi alkoholen til at være butan-2-ol, hvilket også blev bekræftet ved den efterfølgende gaschromatografiske analyse af vores prøve. * Konklusion er derfor at det, ud fra undersøgelser af alkoholens egenskaber, er muligt at afgøre hvilken alkohol, ud af de fem udvalgte, der er i den valgte flaske.

Konklusion.
Kogepunkterne for alkohol 1 og alkohol 4 kan med en afvigelsesprocent på under ½ formodes at være henholdsvis 2-propanol og 1-propanol. Denne formodning styrkes yderligere, eftersom begge alkoholers kan oxideres til carbonylforbindelser, mens kun alkohol 4 kan oxideres videre til carboxylsyre. Det betyder nemlig, at alkohol 1 under de givne forhold kun oxideres til en keton som følge af dens hydroxygruppes placering inde i molekylet, mens alkohol 4, som er en primær alkohol først kan oxideres til aldehyd, og siden til carboxylsyre. Gaschromatografien afgøre endeligt denne formodning, eftersom der ved sammenligning af retentionstid efterviste stor overensstemmelse mellem alkohol 1 og 2-propanol, samt alkohol
4 og 1-propanol - se henholdsvis graf III og IV
Gaschromatografi.
Gaschromatografi er en form for kemisk analyse af rene stoffer eller stofblandinger, som kan bringes på gasfase uden at spaltes. Ved opvarmning bringes alkoholen på gasform, hvorefter den sammen med en konstant strømmende inaktiv gas ledes gennem en kolonne. Efter kolonnen passere alkoholen gennem en detektor, som registrerer en lille spændingsforskel som følge af stoffernes forskellige varmeledende egenskaber. Under de givne forhold, er den tid alkoholen tilbringer i kolonnen en kendetegnende egenskab og kaldes for alkoholens retentiontid. En sammenligning med kendte alkoholers retentionstid giver mulighed for kvalitativt at analysere de ukendte alkoholer.

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[ 1 ]. Informationerne er taget fra en Databog.

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...helps us communicate and show our feelings, ideas, moods, attitudes and expressions at our will. Everybody knows that English is the most popular language nowadays, and it has been for centuries. Besides the popularity, everybody should know that it is one of most important and crucial skills to have for personal success, fun and any other part of life. Which leads to another point, if we could make all people realize that the English language is that important, they would simply try harder to learn it in schools or in their own time. Above all it is a global formula for learning. With this in mind, if one realizes the importance and benefits of something he will try harder to learn it. Besides this realization of the benefits, if we like the subject we are studying, we will most likely learn it faster and with positivity. The English language is an international means for communication and expressing one's feelings anytime and anywhere. Benefits of English language As the quote from Benjamin Lee Whorf says, it shapes the way we think and determines what we can think about, we can conclude that language is in fact a thought and a thinking process. Therefore the conclusion of the quote is that without language, we can not think. Even if we think it is difficult to share and express our thoughts, it is the consequence of thinking. After all, the English language is our best friend" when considering connecting to the outer world. In view of this, it is the main language of...

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