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