CHEMISTRY 31.

1 ORGANIC CHEMISTRY LABORATORY

EXERCISE 10: Aldehydes and Ketones

Submitted by: Abegail Mae S. Ramos II-BS Biology

Laboratory Partners: Gabriel Paulo G. Eleria Marigold P. Araneta II-BS Biology

though methyl ethyl ketone was supposed to be colorless. (1) not enough time for the reaction to occur and (2) quality of chemicals obtained. Test compounds such as benzaldehyde. iodoform test was conducted. Howver. these compounds can be further analyzed as an individual entity and different from each other. As for specific positive test for aldehdyes through Schiff s reagent. Errors occurred in the experiment might be because of two factors. . an aldehyde and methyl ethyl ketone yielded yellow precipitate as an indication of positive test. yielding yellow precipitate to methyl ethyl ketone and 2-butanol as well because it will also oxidize to methyl ketone.4-DNPH is a positive test for both aldehydes and ketones. For specific test of methyl ketones.ABSTRACT 2. yielding brick red precipitate would distinguish aliphatic (formalin/formaldehyde) from aromatic. However. giving a negative result. benzaldehyde and formalin turned its color to magenta. Positive test in Benedict s test. it also turned into magenta. This happened because this test is extremely sensitive and may give false positives. Aldehydes can be classified further into aromatic and aliphatic.

they are derived from alcohols by dehydrogenation (removal of hydrogen). where the aldehyde functional group.CHO. in which a carbon atom shares a double bond with an oxygen atom. for example.a carbon-oxygen double bond. Details vary slightly depending on the nature of the aldehyde or ketone. and 2-butanone. marketed under the name methyl ethyl ketone or MEK. (O'Leary.g. A solution of 2. Introducing Aldehydes and Ketones. 2003) Any of a class of organic compounds.INTRODUCTION Aldehydes and ketones are simple compounds which contain a carbonyl group . a single bond with a hydrogen atom. in carboxylic acids containing -COOH.H . -C=O. Two of the simplest are propanone. from which process came the name aldehyde. (Aldehyde) The aliphatic aldehydes are a homologous series of organic compounds of carbon.4-dinitrophenylhydrazine is dissolved in. & Todd) . The aliphatic aldehydes are named by replacing "-e" at the end of the alkane from which they are derived with "-al".4-DNP or 2. C6H5.as you might find.4-dinitrophenylhydrazine in a mixture of methanol and sulphuric acid is known as Brady's reagent. Wilson. Aromatic aldehydes (e. are also known which undergo a number of chemical reaction which do nor occur for aliphatic aldehydes and which are unique to aromatic aldehydes. The double bond between carbon and oxygen is characteristic of all aldehydes and is known as the carbonyl group.4-dinitrophenylhydrazine is often abbreviated to 2. They are simple in the sense that they don't have other reactive groups like -OH or -Cl attached directly to the carbon atom in the carbonyl group . (Clark. (Shipman. 2. marketed under the name acetone. hydrogen and oxygen. benzaldehyde. The general formula is CnH2n+2. is contained within the molecule. Many aldehydes have pleasant odours. 2000) A ketone is a compound containing a carbonyl group with two hydrocarbon groups attached to it. Formal names for ketones include the prefix from the alkyl group and the suffix one. and in principle.4-DNPH.CHO). and the solvent that the 2. and a single bond with another atom or group of atoms (designated R in general chemical formulas and structure diagrams).

) + + - Table 2. METHODS Methods were taken by following the procedures instructed from Chemistry 31. Test compounds Methyl Ethyl Ketone Benzaldehyde 1-Butanol Precipitate formed (in 15mins.4dinitrophenylhyrdazine reagent.OBJECTIVES The objective of the experiment was to be able to perform different test to aldehydes and ketones test compounds in order to observe and determine its positive and negative reactions. Formation of precipitate from test compounds added with 95% ethanol and 2. Schiff s Test Test compounds Formalin Methyl Ethyl Ketone Benzaldehyde Color Magenta Pink Pink (daker than Methyl Ethyl Ketone) Table 4.1 Organic Chemistry on pages 73-75 with a slight modification of using Methyl Ethyl Ketone instead of acetone as a test compound. Benedict s Test Test compounds Methyl Ethyl Ketone Benzaldehyde 1-Butanol Color after heating green Blue green No color change Color after adding/before heating bluish bluish bluish Table 3. PRESENTATION OF RESULTS Table 1. Iodoform Test .

it is shown in the reaction. The R and R in the reaction stands or any combination of hydrogen and hydrocarbon group. This means that benzaldehyde is an aldehyde. (Clark. Later. For Methyl ethyl ketone. The positive reaction of test compounds with are summarized and generalized below. In this case.4-DNPH For the two compounds. For benzaldehyde.4-DNPH test is a positive test for aldehyde and ketone compounds. The reaction is known as a condensation reaction. A condensation reaction is one in which two molecules join together with the loss of a small molecule in the process.4-DNPH adds the benaldehyde in its attached H to form water. the structure is shown below: . The mechanism is nucleophilic addition-elimination reaction because first the 2. the formed water is then eliminated and the product is an imine. that small molecule is water. Reaction of benzaldehyde and 2. the reaction is shown below: Figure 1. the boxed portion the R and R groups has at least one attached hydrogen.Test compounds Methyl Ethyl Ketone Ethyl alcohol 2-Butanol Color of precipitate formed yellow yellow DISCUSSION The 2. 2004).

the results of the tests were random and would not give a wise interpretation of the reaction of aldehydes and ketones. the expected result must have been no reaction. . Figure 3. 2004) Benedict s solution is a specific positive test for presence of aliphatic aldehyde that would yield brick red color. For Methyl Ethyl Ketone. as well as the time it took for the reaction to occur might be not enough on what was done in the experiment. The reaction is shown below. From the table 2 above. the structure is a ketone. it has an attached hydrocarbon group (as boxed above). Schiff s test is another positive test for aldehydes that would yield colorless to magenta color. Therefore. the results must have been that only formaldehyde. The reaction is shown below. since both has an attached hydrocarbon group. it should have no precipitate and would eventually retain its blue color of the solution. retaining a blue solution. Both benzaldehyde and Methyl Ethyl Ketone yielded with a yellow precipitate because of the presence of carbon-oxygen double bond (Clark. being an aliphatic aldehyde. Nevertheless. in its reaction with 2. yielding brick red precipitate. the reaction is condensation reaction and the mechanism is nucleophilic addition-elimination with formation of water and imine products. The same with benaldehyde s. Benedict s positive reaction Since benzaldehyde is an aromatic aldehyde. 1998) would react. also known as methanal (Harrison. since it is a ketone and definitely not an aldehyde. Methyl Ethyl Ketone As shown in the structure.Figure 2.4-DNPH. The contributing factor of the errors might be the quality of the chemicals given because of changes in color that occurred to some test compounds.

(Experiment 13 Qualitative Tests for Carbonyls. Unknown Carbonyl).Figure 4. In the experiment s result from table 3. The bisulfite reacts with the dye to produce a colorless solution. Schiff s reagent is made by adding the intensely colored triphenylmethane dye called fuschsin to a solution of sodium bisulfate (NaHSO3). The positive reaction of Schiff s test In figure 4. Methyl ethyl ketone should have resulted into colorless color since it is a ketone. This colorless solution will then react with aldehydes but not ketones to produce a new triphenylmethane dye that also has a brilliant purple color. The reason for this mishap might be because the experiment was not handled accordingly because this test is extremely sensitive and may give false positives. . all test compounds had positive result. However. (Experiment 13 Qualitative Tests for Carbonyls. Unknown Carbonyl).

Phenylactaldehyde and benzyl alcohol Phenylactaldehyde is an aromatic aldehyde while benzyl alcohol is an alcohol that will undergo oxidation in Iodoform test. . Secondary alcohols 2-butanol (isobutanol) will also oxidize to methyl ketone and give a positive test with iodoform. it will only react with aldehydes. A light yellow precipitate of iodoform forms immediately with the methyl ketone 2-pentanone. Q/A 1. forming colorless to magenta color. Fuson. & Morrill.4-DNPH. Curtin. (Shriner. specific test for methyl ketones. Reaction of iodoform test The iodoform reaction is a classical test for methyl ketones. In reaction with 2.) Differentiate the following pairs by giving the reagent used in the exercise and the visible result: a. forming yellow precipitate. Methyl Ethyl Ketone from the experiment had positive result. Figure .The general reaction for Iodoform test is shown below. yielding yellow precipitate. and iodoform test. 2001). (Experiment 6 (Organic Chemistry II) Identification of Ketones and Aldehydes) CONCLUSION Aldehydes and Ketones can be distinguished through several tests. Even aldehydes can be further distinguished as aromatic or aliphatic through a positive test in Benedict s of brick red which is characterized as aliphatic aldehyde. it is a positive test for both aldehydes and ketones. forming a yellow precipitate imine. Certain tests have positive specific reactions like in Schiff s reagent.

(blue) n/a Schiff s reagent colorless n/a Iodoform test Yellow ppt. Yellow ppt.4-DNPH Phenylactaldehyde Yellow ppt.4-DNPH Yellow ppt. 2-pentone and 3-pentone 2-pentone is a methyl ketone while 3-pentone is a diethyl ketone. Yellow ppt b. 2. Cyclohexanone and cyclohexyl methyl ether Compounds Cyclohexanone cyclohexyl methyl ether Reaction with 2.4-DNPH Yellow ppt. also known as Schiff bases. Yellow ppt. Compounds 2-pentanone 2-pentanol Reaction with 2. n/a Benedict s Test No ppt. . (compounds having a C=N function). This reaction plays an important role in the synthesis of 2º-amines. benzyl alcohol N/A Compounds Benedict s Test No rxn (blue) N/A Schiff s reagent magenta N/A Iodoform test No ppt.Reaction with 2. (blue) No ppt. what is the purpose of these derivatives? The reaction of aldehydes and ketones with ammonia or 1º-amines forms imine derivatives. Compounds 2-pentone 3-pentone Reaction with 2. Yellow ppt. (blue) Schiff s reagent colorless colorless Iodoform test Yellow ppt. 2-pentanone and 2-pentanol 2-pentanone is a methyl ketone while 2-pentanol is an alcohol that will undergo oxidation in Iodoform test.) In the reaction of 2.4-DNPH Yellow ppt. Benedict s Test No ppt. N/A c. Benedict s Test No ppt. (Carbonyl Reactivity).4-dinitrophenylhydrazine with either aldehydes or ketones you form imines which are derivatives of either aldehydes or ketones. (blue) Schiff s reagent colorless Iodoform test d.

edu/faculty/reusch/VirtTxtJml/aldket1.edu: http://phoenix.d.edu/JCESoft/CCA/CCA5/MAIN/1ORGANIC/ORG12/TRAM12/C/0382204/MOV IE. J.d.gsu.com/EBchecked/topic/13527/aldehyde Carbonyl Reactivity.msu. R. (n. from Chemguide. Wilson. July).hccs. Fuson.com: http://www. Addition-Elimination Reactions of Aldehydes AND Ketones.uk/organicprops/carbonyls/background. (1998.html Clark.3dchem.edu/~nmatsuna/che122/exp13. from Encyclopedia Britannica eb. Formaldehyde . (2001). Unknown Carbonyl. & Todd.uk/organicprops/carbonyls/addelim.liu. C. from SWC2. Retrieved August 23.. 2010.HTM .co.ie/academic/chem/dolchem/html/dict/aldehyde. Iodoform Test for Methyl Ketones. (n.chemguide.)..html Experiment 13 Qualitative Tests for Carbonyls. 2010.chemguide. (n.msu.d. (2004).edu: http://www2. J.). R.).com: http://www.htm Clark.edu/hbase/organic/ketone.asp?ID=101&othername=Methanal O'Leary.pdf Experiment 6 (Organic Chemistry II) Identification of Ketones and Aldehydes. 2010.pdf Harrison.com/moremolecules. from Methanal @ 3Dchem.liu. D. Ketones.com: http://www. Introducing Aldehydes and Ketones.html Shipman. C.d.chem. Y. Aldehydes Aliphatic. L.edu: http://swc2. Retrieved August 23.co. Retrieved August 23.ucc. Methanal . 2010. Retrieved August 23. & Morrill. 2010. (2003). from http://www. (n. from Chemistry Come Alive: http://jchemed. 2010.hccs.wisc. Retrieved August 23. Curtin. Retrieved August 23.chemistry.phy-astr.d. 2010. (n.). Retrieved August 23.edu/pahlavan/2425L6.).britannica. from Hyperphysics***Chemistry: http://hyperphysics. 2010.html Shriner. from Phoenix. 2010. from chemistry. from Chemguide: http://www. D. T. (2000). Retrieved August 23. Retrieved August 23. 2010. K.References Aldehyde.. Retrieved August 23.

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