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Experiment 7- Solubility ClassificationAtienza, Von Ervy; Alcantara, Mark JunGroup 7, Chem 31.1, AB2, Mr. Kevin SisonMay 12, 2010ABSTRACT
Organic substances have different solubility classes. Each class has certain characteristicsunique to it. Determination of the solubility class of different organic substances will help give informationregarding which functional groups were present on it, as well as other characteristics of the compound.The experiment involves the use of different solvents to test various organic compounds. The solventsused were distilled water, ether, 5% NaOH, 5%NaHCO3, 5% HCl, and concentrated sulfuric acid. A testusing litmus paper is also used. The substances were then classified using a dichotomous key diagram.From the results, it can be inferred that certain functional groups dissolve in certain solvents only. Thisinformation is necessary for compound identification.
KEYWORDS: solubility
, o
rganic compounds
, p
olarity, solvent system, solubility classification
Solubility is one method used to identify thepresence of certain functional groups in acompound. Though it is not as accurate as other advanced methods such as using attributes likemelting point, it is still useful. Solubility dependson several factors such as the nature of soluteand solvent, temperature, and pressure.Solubility tests can be considered crudebecause functional groups react differently onvarious substances. The concept of polarity andpH will be greatly used throughout theexperiment. The compounds to be tested willencounter several solvents to determine their solubility in each. A guide will be used to classifyeach compound and the results will betabulated. The information gained will help inidentifying other properties of the compounds.
Several reagents were given for theexperiment. The reagents dissolved werealanine, aniline, benzanamide, benzoic acid,chlorobenzene, cyclohexane, ethylamine, ethylacetate, hexane, E-naphthol, phenol, salicylicacid, and sulfanilic acid. The solvents used weredistilled water, ether, 5% NaOH, 5%NaHCO3,5% HCl, and concentrated sulfuric acid. Twentydrops of the liquid samples and/or 5 g of thesolid samples were used per 4 ml of solvent.The mixtures were placed in 5 ml test tubes.After the experiment, the results were tallied andclassified according to a dichotomous key (seeAppendix 2).
The results were tabulated and classifiedaccording to a dichotomous key. The keyindicates the path to be followed once a solutehas undergone a test for a specific solvent. Thesolutes were then classified into groups whichthey share the same solubility properties.
Sample Water EtherLitmus(R/B/un.)5%NaOH5%NaCO35%HClH2SO4(Conc.)ClassAlanine # x - - - - - S2Aniline x - - x - # - BBenzamide x - - x - x # NBenzoic Acid x - - # # - - A1Chlorobenzenex - - x - x x I
Cyclohexane x - - x - x x IEthylamine # # B - - - - SoEthylacetate # # Un. - - - - S1Hexane x - - x - x x IE-naphtol x - - # x - - A2Phenol x - - # x - - A2Salicylic Acid x - - # # - - A1SulfanilicAcidx - - # # - - A1DISCUSSIONS
The solubility of a solute is themaximum quantity of solute that can dissolve ina certain quantity of solvent or quantity of solution at a specified temperature. Certainfactors affect the solubility of a compound in aspecific solvent or quantity of solution like thenature of the solute and solvent, melting point,molecular weight and the presence and positionof the functional groups present in thecompound.Like dissolves like. Most organiccompounds have both polar and non-polar parts,so the solubility of these compounds in certainsolvents depends on the balance of the polar and non-polar parts of the compound. As thehydrocarbon portion of the increases, the morenon-polar it becomes; the less soluble in water and the more soluble in a non-polar solvent itwill be.Generally, solubility of organiccompounds is inversely proportional to itsmelting point meaning the higher the meltingpoint of the compound, the harder it will be todissolve the compound.
Molecular weight is anotherfactor. An increase in molecularweight leads to the increase in theintermolecular forces of attraction (ina solid) which will then lead to adecrease in solubility.
Usually, compounds that have branchesare more soluble than a corresponding straightchain compound without branches. This isbecause branches lowers intermolecular forcesand thereby decreases intermolecular attraction.The presence of functional groups alsoaffects solubility of compounds. These functionalgroups may form polar bonds or induce polarityin a molecule. Functional groups also giveinformation on the acidity of the compound.Acidity of the substance tells whether thesubstance will dissolve or not in basic or acidicsolvents/solutions. The trend is that strong acidsare soluble in strong and weak bases/basicsolutions while weak acids dissolve only instrong bases/basic solutions.
Water as a solvent
Water is a poor solvent for hydrocarbons.
Presence of double bonds, triple bondsor aromatic rings does not affect thepolarity greatly –similar to alkanes intheir solubility.
Substituting halogen for hydrogendecreases the water solubility.
Salts are extremely polar and areusually water soluble.
Acids and amines are more soluble thannonpolar compounds (due to H-bonding).
Solubility of amines decreases as thebasicity decreases.
Many tertiary amines are more solublein cold than in hot water (at lower temperatures, the solubility of thehydrates is involved).
Solubility in Water 
In general, most organic compoundsthat have no more than six carbon atoms aresoluble in water. However, there is an indefiniteborderline with respect to the solubility of carboncompounds in distilled water. For example, afew six-carbon alcohols, such as cyclohexanol,are soluble in water even if it is said thatalcohols are water-soluble only if they havefewer than six carbons. The same kind of borderline solubility is to be found among allfunctional-group classes whose low molecular weight members are soluble in water.
Multifunctional compounds, for example,polyhydroxy compounds such as carbohydrates,are often very soluble in water. Solubilitydepends on the exact structure of a compound,not only on the number of carbon atoms that itcontains, and it is necessary to interpretsolubility characteristics cautiously.
Solubility in Ether 
Ether is a polar molecule wherein theoxygen has a partial negative charge and eachcarbon attached to it bears a partial positivecharge. Since the solubility behavior of water soluble compounds gives no information aboutthe presence of acidic or basic functionalgroups, their solubility in ether are first tested.Compounds which are insoluble in ether areautomatically placed in class S. Thesecompounds are too polar to dissolve in ether,such as salts of organic acids, aminehydrochlorides, amino acids and polyfunctionalcompounds with hydrophilic functional groups.Acidity of the aqueous solutions of ether solublecompounds is tested using litmus paper whichturns blue when pH is >8.3 and turns red whenpH is <4.5. Ether soluble compounds that turnslitmus paper to red is classified under Sa. Thosethat turn the litmus paper to blue are under theSb classification and those that did not reactwith the litmus, Sg.
Solubility in NaOH
Solubility of substance depends on itspH level and on certain functional groupspresent in the substances. Solubility of organiccompounds is a consequence of the presence of acidic hydrogen which can be one bonded to O,N, S, or even C. Organic acids, which areinsoluble in water, normally dissolve in a NaOHsolution. The pH of this solution is greater than14, so any acid whose pKa < 12 is convertedalmost entirely to its conjugate base. Thus,water-insoluble carboxylic acids and phenols willboth dissolve in sodium hydroxide solution.Esters with five or six carbon atoms thatare almost completely soluble in water may behydrolyzed by continued shaking with 5% NaOHsolution. The alkali should not be heated and thesolubility or insolubility should be recorded after 1-2 minutes.
Solubility in 5% NaHCO
When a compound is insoluble in water but soluble in NaOH, a third solubility test using5% sodium bicarbonate is called for. It wasstated earlier that a strong bases reacts readilywith strong and weak acids. That was whathappened in the NaOH test. Solubility in 5%NaHCO
, a weak base, differentiates a strongacid to a weak one since only the strong acidsare expected to react with NaHCO
. Sodiumbicarbonate is a weaker base than sodiumhydroxide; a 0.6 M NaHCO3 solution has a pHof approximately 9. It dissolves a water insolubleorganic acid whose pKa is less than 7.5 byconverting it to a water-soluble salt. Whereascarboxylic acids (pKa < 5) dissolve in a sodiumbicarbonate solution, most phenols do not butthose containing strong electronegative groupswhich increase the acidity of phenol do.
Solubility in 5% HCl
The only organic compounds that areinsoluble in distilled water but soluble in dilutehydrochloric acid solution are amines, the major class of basic organic compound. Nearly allamines undergo reaction with HCl to produceionic ammonium salts that are almost alwayssoluble in water. This behavior is the same for tertiary (R3N), secondary (R3NH), and primary(RNH2) amines. Solubility of amines in diluteHCl is connected with the tendency of the lonepair of electrons of N to bond with the proton,resulting in salt formation. In general, aliphaticamines are readily soluble in dilute HCl. Whenalkyl groups are bulky such as in secondary andtertiary amines, solubility in dilute HCldecreases. This is a consequence of stericinhibition of the approach of the acid to bondwith the lone pair or the instability of the saltformed as a result of steric crowding.
Solubility in Concentrated H
Many compounds which are neutraltowards 5% HCl behave as bases in more acidicsolvents like concentrated H
is used with neutral, water insolublecompounds containing no elements other thanC, H, and O. Solubility in or any other evidenceof a reaction with H
indicates the presenceof an oxygen atom or of a reactive hydrocarbonfunction such as an olefinic bond or easilysulfonated aromatic ring (class N).Solubility depends on capability tosubstance to undergo sulfonation. If thesubstance is unsaturated or contains a

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