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Carbonyl Compounds Aldehyde and Ketones

Carbonyl Compounds Aldehyde and Ketones

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Published by Jason Raquin Roque

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Published by: Jason Raquin Roque on May 19, 2012
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Carbonyl Compound: Aldehydes and Ketones
Roque, Jason R.Frias, Abigail Pauline F.De Ramos, Jason Jalou
Bachelor of Science in Biology – Major in Human BiologyCollege of ScienceDe La Salle University – DasmariñasDasmariñas, Cavite, Philippines ABSTRACTIn this experiment the solubility and reactions of different aldehydes and ketoneswere tested and seen. 5 drops of acetone, acetaldehyde, benzaldehyde andcyclohexanone were prepared in separate test tubes. The samples were added 5 drops of water and sodium hydroxide each test tube in different set ups. cyclohexanone andacetone were found to be soluble in water and none of any compounds were soluble insodium hydroxide. In 2,4-DNP tests, 1ml of 95% ethanol and 1mL 2,4-DNP were added ineach sample. All compounds resulted to a bright yellow or orange precipitate that showedthe carbon-oxygen double bond in aldehyde and ketone. In Tollen's test, 2ml Tollen'sreagent was added in each sample and was kept for 10 minutes. In this test the oxidationwill determine the presence of aldehyde and ketone. Only acetaldehyde andbenzaldehyde were oxidized. In Iodoform test, 2ml of distilled water was added to thesample, placed inside the water bath with the temperature of 60 for several minutes thenthe Iodoform reagent was added. This test was done to determine the presence of CH3CO in aldehyde and ketone. Only aldehyde and acetone were positive in this test. Another test to determine the oxidation reaction was the Jone's test where 4 drops of chromic acid solution were added and stand for 10 minutes. Different tests were done todetermine the presence of aldehyde and ketone.INTRODUCTION Aldehydes and ketones have same chemistry polarity. Its bonding affects its reactivity. Carbonylgroup is a divalent chemical unit consisting of a carbon (C) and an oxygen (O) atom connected by adouble bond. Both are simple carbonyl compounds which contains the carbonyl group, -C=O. it has noother reactive group that attaches to the carbon atom itself. (3) Aldehydes and ketones are organic compounds which incorporate a carbonyl functional group,C=O. The carbon atom of this group has two remaining bonds that may be occupied by hydrogen or alkylor aryl substituents. If at least one of these substituents is hydrogen, the compound is an aldehyde. If neither is hydrogen, the compound is a ketone. (2)Figure 1. Structure of Aldehyde and Ketone
Digitally signed by Jason RaquinRoqueDN: cn=Jason Raquin Roque, o,ou, email=jason_mike15@yahoo.com, c=PHDate: 2012.05.15 14:13:58 +08'00'
 
 Aldehydes and ketones have higher boiling point than alkenes but lower boiling point than alcoholbecause it is more polar but cannot form intermolecular hydrogen bonds to other carbonyl groups. Thesetwo compounds are also known to be soluble in water but falls when chain lengthens. (4)In aldehydes, the carbonyl group has a hydrogen atom attached to it together with either asecond hydrogen atom or, more commonly, a hydrocarbon group which might be an alkyl group or onecontaining a benzene ring. (14)Figure 2. Examples of AldehydesIn ketones, the carbonyl group has two hydrocarbon groups attached. Again, these can be either alkyl groups or ones containing benzene rings. Again, we'll concentrated on those containing alkyl groups just to keep things simple. Notice that ketones never have a hydrogen atom attached to the carbonylgroup. (14)Figure 3. Examples of KetonesMATERIALS / REAGENTS & EXPERIMENTAL PROCEDUREThe experimenters placed 3-5 drops of each sample (acetone, acetaldehyde, benzaldehyde andcyclohexanone) in dry test tubes and prepared on various tests. There will be two category of tests for this experiment, the solubility test which comprises of solubility in water and sodium hydroxide adchemical test which includes Tollens’ test, 2,4-DNP, Iodofrom test and Jones’ test. After each test, their reactions were observed and classified as insoluble/non-reactive, slightly soluble/slow reaction andsoluble/fast reaction.The solubility test involved: solubility in water, add 5 drops of distilled water in each sample andobserve, while in NaOH, add 5 drops of 10% NaOH in each sample and observe.For chemical reactions - 2,4- DNP test: Add 1 mL (10 drops) of 95% ethanol and 1 mL 2,4-dinitrophenylhydrazine reagent per sample. Shake and observe reaction. Tollen’s test: Add 2 mL (20drops) of Tollen’s reagent per sample. Stand for 10 minutes and observe reaction. Iodoform test: Add2mL of distilled water per sample. Place test tube in hot water bath (60
˚
C) for 3-4 minutes. Add lodoformreagent while shaking until brown color appeared for 2 minutes. Keep in water bath again for 5 minutes.Observe reaction. Jones’ Test: Add 4 drops of Jones’ Reagent (Chromic Acid) while shaking in eachsample. Stand for 10 minutes and observe reaction.DATA & RESULTSThe reaction of the different samples is classified into two different tests: the solubility test and thechemical test. The solubility test is comprises with solubility in water and in sodium hydroxide, while for the chemical tests are 2,4-DNP test, Tollen’s test, Iodoform test and lastly the Jone’s test. Below is thetable for the reaction of each sample into different tests.
 
Table 1. Reaction ProfileSOLUBILITY TEST CHEMICAL TESTSolubility inwater Solubility insodiumhydroxide2,4 –DNPTestTollen’sTestIodoformTestJone’sTestVisible + ResultSAMPLESacetone ++ - ++ - ++ -acetaldehyde ++ - ++ + - -benzaldehyde + ++ ++ ++ - ++cyclohexanone - ++ ++ - - +SOLUBILITY IN WATER:The carbonyl residue in acetone (CH
3
COCH
3
) which is polar in nature due to the difference inelectronegativity between C and O, forms an overall molecular dipole in acetone. This molecular dipole isnearly identical to water--in fact, acetone has a dielectric constant of about 77 while water's dielectricconstant is about 80 at room temperature and thus would be soluble in water.Hydrogen bonding does occur between acetone and water as the oxygen of acetone's cabonylcan hydrogen bond with the O-H bonds of water. However, the presence of such hydrogen bonding wouldin fact only lend to the ability of the two types of molecules to be miscible with each other. Acetaldehyde is soluble in all proportions. The reason for the solubility is that acetaldehyde can'thydrogen bond with themselves; they can hydrogen bond with water molecules.One of the slightly positive hydrogen atoms in a water molecule can be sufficiently attracted toone of the lone pairs on the oxygen atom of an aldehyde or ketone for a hydrogen bond to be formed.Figure 4. Bonding of Water and Carbonyl GroupBenzaldehyde is soluble in water 0.6 g/100 ml (20 °C). It has fairly low solubility because it is anon-polar hydrocarbon with a low percentage of oxygen in the molecule.Cyclohexanone is slightly soluble in water (5-10 g/100 mL), but miscible with common organicsolvents. But in the experiment the cyclohexanone is not soluble in water. It may be caused by theamount of cyclohexanone and the solvent that makes it insoluble in water.

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