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Formal Report, Carboxylic Acid and Derivatives

Formal Report, Carboxylic Acid and Derivatives

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Classification Tests Carboxylic Acid and Derivatives
Francese Ilagan, Jose Lacorte, Judy Laureta, Regine Li and
Vicente Romeo M. Macatangay Jr
Group 6
2G PHARMACY
Organic Chemistry Laboratory
Abstract
The objective of this experiment was to identify and differentiate the reactivities of carboxylic acid derivatives and todistinguish each carboxylic acid derivatives using different classification tests, namely hydrolysis, alcoholysis, aminolysis andhydroxamic acid test. These tests will yield either positive or negative results. They will determine the presence of the carboxylic acids and itsderivatives.
 
Introduction
Carboxylic acids (R-COOH) are polarcompounds which contain a carboxyl group composedof a carbonyl group and a hydroxyl group on the samecarbon atom. They are the most abundant of allorganic compounds. Like alcohols, carboxylic aids formstrong intermolecular hydrogen bonds. Most carboxylicacids in fact exist as dimmers which are held togetherby two hydrogen bonds, because of this hydrogenbonding, their boiling points are significantly higherthan other compounds.
Smaller carboxylic acids aresoluble in water, whereas higher carboxylic acidsare less soluble due to the increasinghydrophobic nature of the alkyl chain
. Theselonger chain acids tend to be rather soluble in less-polar solvents such as ethers and alcohols. Otherfunctional group combinations with the carbonyl groupcan be prepared from carboxylic acids, and are usuallytreated as related derivatives. There are five commonclasses of Carboxylic acid derivatives: Acyl Halide,anhydride, ester, amide, nitrile. Although nitriles donot have a carbonyl group, their functional carbonatoms all have the same oxidation state. There aremany ways to synthesize Carboxylic acids. They can beprepared from oxidizing primary alcohols with aqueousCr0
3
or Na
2
Cr
2
0
7
to give carboxylic acids or the can beprepared from nitriles by a hydrolysis reaction with hotaqueous acids or bases.
Experimental
 
1.
 
Compounds testeda.
 
Acetyl Chlorideb.
 
Acetyl anhydridec.
 
Ethyl acetated.
 
Benzamidee.
 
Acetic acidf.
 
Acetic anhydrideg.
 
Ethyl acetateh.
 
AcetamideProcedure2.
 
Hydrolysis of acid derivativesa.
 
Acyl halides and Acid Anhydridesi.
 
1 ml of water was placed in atest tube.ii.
 
10 drops of acetyl chloride/acetic anhydride were added tothe test tube with 1 ml wateriii.
 
The resulting mixture wasdivided in to two portionsiv.
 
In the first portion, 1 ml of 2%AgNO
3
was added.v.
 
In the second portion, 1 ml of saturated NaHCO
3
was addedb.
 
Estersi.
 
2 ml of 25% NaOH solutionwas added to 1ml of Ethylacetate. the mouth of the testtube was covered with amarble and then subjected to aboiling water bath for 5minutes.ii.
 
The sample was neutralizedwith 10% HCl solution.c.
 
Amidesi.
 
1ml of benzamide was treatedwith 5ml of 10% NaOH solutionand was heated to boilingii.
 
Litmus paper was then heldagainst the mouth of the testtubed.
 
Alcoholysis: Schoten-BaumannReactioni.
 
A mixture of 10 drops of aceticacid, 1 ml ethanol and 5 dropsof conc. H
2
SO
4
was heated till
 
warm and subjected to a waterbath for 2 minutese.
 
0.5 ml of ethanol, 1ml of water and0.2ml of acyl halide or acid anhydridesample are put in another test tube. Inthe mixture was added 2ml 20% NaOHsolution. A cork or parafilm were usedas stopper for the test tube and wasshaken for several minutes.3.
 
Aminolysisa.
 
A few drops of acetyl chloride or aceticanhydride sample were added to 0.5mlaniline and was transferred to a newtest tube containing 5ml water.b.
 
Hydroxamic Acid TestPreliminary testc.
 
2 drops of the sample were mixed with1ml of 95% ethanol and 1 M HCl. 1drop of 5% FeCl
3
was added to thesolution. It is noted that if anothercolor other than yellow is obtained, thetest would not be used. Otherwise, thetest is conducted as followsd.
 
2 drops of the sample were added to 2ml of alcoholic NH
2
OHHCl and ml of 1MKOH. The solution was heated in aboiling water bath for 2 minutes. Afterwhich it was cooled and then 1ml of 5% FeCl
3
was added.
Results and Discussion
1.
 
Hydrolysis of Acid Derivatives
Hydrolysis of AcidDerivativeObservations
Acetyl Chloride Warming effectWhite cloudy precipitateEvol. Of CO
2
Acetic Anhydride No warming effectNo precipitateEvolution of CO
2
Ethyl Acetate Fruity
plastic balloonlike odorBenzamide Red litmus paper turnedblue(basic) (presence of Ammonia) with aminelike odorTable 1 shows the tabulated results of Hydrolysisof Acid Derivatives
The acid halides and anhydrides acetyl alcoholand acetic anhydride both showed evolution of CO
2
when NaHCO
3
was added.Upon addition of water andAgNO
3
,
 
Acetyl chloride showed warming effect and awhite cloudy precipitate, respectively; however aceticanhydride did not show both warming and precipitate.The Ester, Ethyl acetate, after neutralizing with10% HCL and water bathing, expressed a Fruity/Plasticballoon like odorThe Amide, Benzamide, upon heating turnedbasic, indicating presence of ammonia with amine likeodor.
2.
 
Alcoholysis: Schotten
Bauma ReactionFigure 2.1 shows Acetyl Chloride
Alcoholysis Observations
Acetic Acid Plastic balloon like odorNo layer formedAcetyl Chloride Plastic balloon like odorNo layer formed
Table 2 shows the tabulated results of AlcoholysisThe carboxylic acid, acetic acid, upon waterbathing for 2 minutes exhibited plastic balloon likeodor, but no layer was formedAcyl halide, Acetyl chloride after addition of 20% NaOH solution and agitation, exhibited also aplastic balloon like odor and formation of no layers.
4.
 
Aminolysis: Anilide Formation
Aminolysis Observation
Acetyl Chloride Formation of whiteprecipitate
 
Acetic anhydride Without precipitateFormation of layers
Table 3 shows the tabulated results of AminolysisAcetyl Chloride exhibited formation of whiteprecipitate upon addition of 0.5ml anilline. AceticAnhydride however did not form any precipitate,but it did form layer.
4. Hydroxamic Acid testFigure 4.1 shows preliminary testresults of Ethyl Acetate and AcetamideFig. 4.1 Shows Ethyl Acetate andAcetamide Respectively
Hydroxamic AcidTestObservations
Preliminary Test Yellow Solution isobtainedEthyl Acetate Deep burgundy colorAcetamide Orange-red color
Table 4 shows the tabulated results of Hydroxamic Acid TestA Preliminary test was done to eliminate those phenolsand enols that give colorswith ferric chloride in acidic solutionthat would therefore give false positive result in the ferrichydroxamic testEthyl acetate yielded deep burgandycolorwhich was a positive resultAcetamide gave an orange-red color which isalso a positive result
References
Bayquen, Aritea V. R.Ph., Ph.D, Cruz, Cristina T.,R.Ph.,de Guia, Roldan M., R.Ch.,M.S. Bioscie, Lampa,Florence F., B.S. BioChem., Pena, Gardee T.,R.Ch.,M.S. Chem, Sarile, Angelita S. Ph.D., Torres,Peter C.,R.Ch.,M.S. Chem.(2009).Lab Manual inOrganic Chemistry. Organic ChemistryGroup.University Of Santo Tomas.Morrison, R.N. Boyd Organic Chemistry, 6
th
Ed.(1992)McMurry, J. Foundations Of Organic Chemistry.C&EPublishing Inc.Retrieved September 25,2012 fromhttp://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/crbacid1.htmRetrived September 25, 2012 fromhttp://www.chemguide.co.uk/organicprops/acids/background.html

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