*

Cala, Jean Kathleen B.

Vera Cruz, Aika Gail J.

*Solubility of organic compounds is a

property that provides information regarding the identity and the structure of the substance such as its functional groups and what elements it contains. Solubility depends on various factors such as the nature of the solute, temperature, and pressure.

*In general, the tendency of a solute

to dissolve in a solvent basically depends on the ability of the solute to interact effectively enough with the solvent molecules.

*The dissolving process involves

breaking of attractive forces among solute and solvent particles, but the breaking of the forces between the solute particles and the solvent particles is also observed.

*Polarity is one great factor for it

determines what reacts with what as indicated in the Like dissolves like principle.
because they interact with each other through dipole-dipole.

*A polar solute dissolves in a polar solvent

*Nonpolar solutes and nonpolar solvents

interact with each other through London dispersion forces (LDF). The presence of an acidic CO2H or basic NH2 group in a watersoluble compound can be detected by low or high pH, respectively, of the solution.

*In the experiment, the solubilities

of 14 different organic compounds were evaluated by testing it to different solvent systems. Different procedures were conducted to solid and liquid samples.

*About 30mg of each sample were obtained

in different test tubes. For every test tube, 20 drops of the different solvent systems were added. This was repeated seven times for there are 7 solvent systems to be tested. Each sample was classified as completely soluble = +++, partially soluble = ++, slightly soluble = +, and insoluble = X, depending on its reaction to the solvent.

OH

Benzoic Acid

Alanine

Salicylic Acid

Sulfanilic Acid

Phenol

*2 drops of each sample was obtained

in different test tubes. 20 drops of the solvent was then added to the test tube, as well. This was procedure was repeated for each solvent. The dissolution of the sample was determined and classified as completely miscible = +++, partially miscible = ++, and immiscible = X.

Hexane
Acetic Acid

Ethylacetate

Aniline

Chlorobenzene
E-naphthol Ethylamine

Benzene

Cyclohexane

Benzamide

Sample Alanine Aniline Benzamide Benzene Benzoic Acid Chlorobenze ne Cyclohexane Ethylamine Ethylacetate Hexane E-naphtol Phenol Salicylic Acid Sulfanilic Acid

Water ++ X X X X X X +++ +++ X X ++ X +

5% NaOH +++ X X ++ +++ +++ X X +++ X ++ +++ ++ +++

5% HCl ++ +++ X +++ ++ ++ X +++ X ++ +++ +++ +++ +++

5%NaHCO3 Ether ++ X + +++ +++ +++ X X ++ ++ ++ X +++ +++ X +++ +++ X +++ X +++ +++ +++ +++ +++ +++ +++ +

Conc. H2SO4 X +++ ++ X + + X X X X ++ +++ ++ ++

85% H2PO4 + ++ + X ++ ++ ++ X ++ X + X + ++

Sample Alanine Aniline Benzamide Benzene Benzoic Acid Chlorobenze ne Cyclohexane Ethylamine Ethylacetate Hexane E-naphtol Phenol Salicylic Acid Sulfanilic Acid

Water ++ X X X X X X +++ +++ X X X X +

5% NaOH +++ X X ++ +++ +++ X X +++ X ++ +++ ++ +++

5% HCl ++ +++ X X X X X +++ X X +++ +++ +++ +++

5%NaHCO3 Ether ++ X + +++ +++ +++ X X ++ X ++ X +++ +++ X +++ +++ X +++ X +++ +++ +++ +++ +++ +++ X X

Conc. H2SO4 X +++ ++ X + + X X X X ++ +++ ++ ++

85% H2PO4 + ++ + X ++ ++ X X ++ X + X + ++

*In considering solubility in water a

substance is arbitrarily said to be soluble if it dissolves to the extent of 3g per 100mL of solvent.

*Water is a poor solvent for

hydrocarbons. The introduction of halogen atoms does not alter the polarity appreciably. Organic salts, on the other hand, are water soluble. soluble than neutral compounds.

*Acids and amines are generally more

*Branching of the alkyl chain of the

molecule lowers intermolecular forces between its molecules, causing greater solubility in water. This occurs simply because the molecules of the branched compound are more easily separated from one another. which contain polar groups of oxygen, nitrogen or sulfur, will often be soluble in water. Compounds with five or six carbons with those elements will often have borderline solubility or be insoluble.

*Compounds with four or less carbons, and

*Acids are soluble in 5% NaOH, a strong base, but

only strong acids are soluble in 5% NaHCO3, a weak base. sulfinic acids, phenols with e-withdrawing groups in the ortho- and/or para- positions primary and secondary nitro compounds, arylsulfonyl derivatives of primary amines, unsubstituted arylsulfonamides, oximes, thiophenols
to dissolve to any measurable extent in NaOH solution.

*Strong acids: Carboxylic acids, sulfonic acids, *Weak acids: phenols, some enols, imides,

*Aldehydes and ketones are far too weakly acidic

*Aliphatic amines, primary, secondary, and *Aryl groups diminish the basicity of the

tertiary, form salts with hydrochloric acid. Hence, they are soluble in dilute HCl. amine. Primary aromatic amines, although more weakly basic than primary aliphatic amines, are soluble in dilute HCl. Diarylamines and triarylamines are not soluble. sufficiently high molecular weight to be water insoluble are soluble in dilute HCl.

*Disubstituted amides (RCONR2) which are of

*Ether is a slightly polar molecule. *A compound that dissolves in both

water and ether means that it has both a considerable nonpolar and polar characteristics.
derivatives as well as salts are too polar to dissolve in ether while monofuctional compounds are soluble in ether.

*Polyfunctional compounds and

*Conc. H2SO4 is used with neutral, water-

insoluble compounds containing no elements other than carbon, hydrogen, and oxygen. sulfonated, or possesses a functional group containing oxygen, it will dissolve in concentrated H2SO4. derivatives are insoluble in concentrated H2SO4.

*If the compound is unsaturated, is readily

*Alkanes, cycloalkanes, and their halogen

*Simple aromatic hydrocarbons, and their

halogen derivatives do not undergo sulfonation and are insoluble in concentrated H2SO4. However, the presence of two or more alkyl groups on the aromatic ring permits the compound to be sulfonated. as is sulfuric acid. It is capable of dissolving most of the oxygen containing compounds such as alcohols, aldehydes, and esters, but is not able to dissolve unsaturated hydrocarbons such as alkenes, alkynes or aromatics.

*Phosphoric acid is not nearly as strongly acidic

*The solubility or miscibility of a

solute to a solvent is generally dependent on its nature. The solubility classification of an organic compound is based on its composition, structure, properties and presence of functional groups.

*Construct a schematic diagram

for the determination of the solubility characteristics of organic compounds.

Insoluble Soluble Ether

Salts of organic acids, amine hydrochlorides, amino acids, polyfunctional compounds with hydrophilic functional groups: carbohydrates (sugars), polyhydroxy compounds, polybasic acids, etc.

Acidic Monofunctional carboxylic acids with five carbons or fewer; arylsulfonic acids Soluble Basic Monofunctional amines with six carbons or fewer Neutral Monofunctional alcohols, aldehydes, ketones, esters, nitriles, and amides with five carbons or fewer Soluble Soluble 5% NaHCO3 Insoluble Strong organic acids: Carboxylic acids with more than six carbons; phenols with electron-widthrawing groups in the ortho and/or para position(s); diketones (1,3 diketones) Weak organic acids: phenols, enols, oximes, imides, sulfonamides, thiophenols, all with more than five carbons; diketones; nitro compounds with - hydrogens Aliphatic amines with eight or more carbons; anilines (only one phenyl group attached to nitrogen); some ethers Miscellaneous neutral compounds containing nitrogen or sulfur and having more than five carbon atoms Alcohols, aldehydes, ketones, esters with one functional group and more than 5 but fewer than 9 carbons, ethers, epoxides Alkenes, alkynes, some aromatic compounds

Water

Insoluble

5% NaOH

Soluble

Borderline Insoluble 5% HCl

Soluble Soluble 85% H3PO4 Insoluble

Insoluble

Conc. H2SO4 Insoluble

Saturated hydrocarbons, haloalkenes, aryl halides, other deactivated aromatic compounds, diaryl ethers

* Castro, A. (2009). Solubility of organic compounds. Unpublished manuscript,

Physical Sciences Department, De La Salle University - Dasmarias, Dasmarias, Cavite.

* Classification of organic compounds by solubility. (2004, October 28).

Retrieved from http://opencourseware.kfupm.edu.sa/colleges/cs/chem/chem303/files\3Lecture_Notes_CHEM-303_(Chapter_5).pdf http://faculty.swosu.edu/william.kelly/pdf/qo3.pdf

* Kelly, B. (1997, December 31). Organic qualitative analysis. Retrieved from

* Shriner, R. L., Fuson, R. C., & Curtin, D. Y. (1965). The systematic

identification of organic compounds (5th ed.). New York: Wiley.

* Trainor, D., Huang, A., & Moyer, J. (2012). Procedure for determining

solubility of organic compounds. Retrieved from http://www.wellesley.edu/Chemistry/chem211lab/Orgo_Lab_Manual/Ap pendix/ClassificationTests/solubility.html