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29, 2011 I. Introduction Solvation or the dissolving process involves breaking and reestablishing or attractive forces between solute and solvent particles. Furthermore, solubility is defined as the amount of solute that can dissolve in a certain amount of solvent at a certain temperature. It is generally governed by the principle “like dissolves like.” This means that polar solutes dissolve in polar solvents, likewise, nonpolar solutes dissolve in nonpolar solvents. The solubility of a compound is determined by many factors. It is primarily affected by the compounds’ nature/polarity but it is also affected by temperature, molecular weight, structure of the compound, acidity or basicity of the compound, intermolecular forces of attraction, and the over-all pressure aids in the dissolution of the solute in the solvent. At the end of this experiment, students should be able to determine the solubility, along with the acidity and basicity, of different organic compounds, namely: alanine, aniline, benzamide, benzoic acid, chlorobenzene, cyclohexane, ethylacetate, hexane, E-/α-napththol, dimethylamine, phenol, salicylic acid, and sullfanic acid. Knowledge in the solubility of compounds is chiefly used in identification and analysis of unknowns usually handled in laboratories. It also helps in giving important information on the structural composition of a given compound, which is especially useful in the field of Organic Chemistry. Better understanding of the behavior of different compounds would be beneficial for experiments and studies in the future. II. Methods Using the solubility diagram and results table provided, the students determined the different solubility classification of the following sample solutes: alanine, aniline, benzamide, benzoic acid, chlorobenzene, cyclohexane, ethylacetate, hexane, E-/α-napththol, dimethylamine, phenol, salicylic acid, and sulfanilic acid. The solvents to be used in this experiment are the following: water, ether, litmus (to determine the acidity/basicity), 5% NaOH, 5% NaHCO3, 5% HCl, and concentrated H2SO4. One (1) drop of liquid sample or 5mg of powdered solid sample was dissolved in 0.2mL solvent. The solubility tests were done in 5mL test tubes.
and some N. and unsaturated hydrocarbons. hydrochloric acid.N-dialkyl-carboxamides. hydroxy acids. hydrochloric acid classifies compounds soluble to as bases. polycarboxylic acids. The solvents used in this experiment are water. sulfonic acids. sulfuric acid classifies compounds soluble to it as neutral and those insoluble are inert. Ether classifies compounds as acidic. They are partly polar which makes them soluble to both water and ether. sodium bicarbonate. anhydrides. sodium hydroxide. Sodium hydroxide classifies compounds soluble to it as acids. In the experiment. They are soluble in 5% NaOH but insoluble to both water and 5%NaHCO3 and in the experiment phenol and E-/α-naphthol belong to the A 2 group. AS or strong acidic group has members that are strong proton donors. Benzamide is a member of this group and it is insoluble in water. This group includes primary. They are electron pair donors and they turn red litmus to blue. enols. and sulfuric acid. primary and secondary nitro compounds. With these being said. polyhalide nitro group and aldehyde group substituted phenols. esters. S N or water-soluble neutral group are monofunctional alcohols. and sulfanomides of secondary amines. On the other hand.III. They are insoluble in water because of the presence of benzene rings in these compounds. Also. nitriles and amides which are partially polar and they are soluble in water and ether. saturated . The next is the S B or the water-soluble base group. and carbohydrates. Sodium bicarbonate classifies soluble compounds as strong acids and weak acids if it is otherwise. The NM or miscellaneous neutral group compounds contain sulfur and nitrogen such as aromatic nitro compounds. and sulfanilic acid. The B or basic group has members that are electron pair donors that form hydroxide anions in aqueous solutions. The N or neutral group compounds are mostly containing oxygen and lacks sulfur or nitrogen. they turn blue litmus to red. nitriles. and sulfonamides of primary amines. amino acids. and electron-withdrawing group (ortho and/or para position) substituted phenols and examples of this group in the experiment are benzoic acid. An example of this is the alanine. tertiary amines except diary and triaryl amines. aldehydes. Lastly. carboxylic acid salts. the solute methylamine* is a member of this group. Water classifies compounds soluble to it as polar and nonpolar if it is otherwise. aniline is an example and it is insoluble in water because of the presence of a benzene ring. an alpha amino acid. basic. organic compounds therefore can be divided into ten groups. and 5% NaHCO3. salicylic acid. An example of this in the experiment is the solute ethylacetate. aldehydes. In the experiment. polyhydroxy alcohols. Results and Discussion Different solvents have different roles in the solubility classification of organic compounds. amides. ethers. esters. AW or weak acidic compounds include phenols. ketones. the I or inert group compounds include alkyl and aryl hydrocarbons. Lastly. Members of this group include alcohols. hydrazines. S 2 or ether-insoluble group consists of polar compounds which include amine salts. They are insoluble to water but soluble to 5% NaOH and 5% NaHCO 3 and the reaction yields a water-soluble salt. ketones. 5% NaOH. The first group would be the SA group or the water-soluble acid group. secondary. ether. and neutral. The members of this group are carboxylic acids.
and diaryl ether. Table 1: Solubility of Different Solutes and Solvents Water Alanine Aniline Benzamide Benzoic acid Chlorobenzene Cyclohexane Ethylacetate Hexane E-/α-napththol Dimethylamine Phenol Salicylic acid Sulfanilic acid insoluble insoluble insoluble insoluble insoluble insoluble insoluble insoluble insoluble insoluble slightly soluble slightly soluble slightly soluble Ether insoluble soluble insoluble slightly soluble insoluble soluble soluble insoluble soluble insoluble soluble slightly soluble insoluble Litmus B to R B to R B to R same same same same B to R same same B to R B to R B to R 5% NaOH insoluble insoluble insoluble slightly soluble insoluble insoluble insoluble insoluble slightly soluble insoluble insoluble slightly soluble slightly soluble 5% NaHCO3 insoluble insoluble soluble insoluble insoluble insoluble soluble soluble insoluble soluble insoluble soluble slightly soluble 5% HCl insoluble insoluble insoluble insoluble insoluble insoluble soluble soluble insoluble soluble insoluble insoluble insoluble Conc. Chlorobenzene.hydrocarbons. H2SO4 insoluble soluble insoluble insoluble insoluble insoluble soluble insoluble slightly soluble evolution of gas insoluble soluble insoluble Figure 2: 3: Solubility of Aniline Figure Solubility of Alanine Figure 1: Diagram of Solubility Classification . cyclohexane and hexane represent this group in the experiment.
Figure 4: Solubility of Benzamide Figure 5: Solubility of Benzoic Acid Figure 7: Solubility of Cyclohexane Figure 6: Solubility of Chlorobenzene IV. b) Water-soluble Base (SB) . They are good proton donors and they turn blue litmus to red. Answers to Guide Questions: 1. Give the rationale behind the solubility of the compounds in each solubility class. a) Water-soluble Acid (SA) Compounds in this group are partially polar so they are soluble in both water and ether.
They are soluble in 5% NaOH which produces water-soluble salts. they are insoluble in 5% NaHCO3 because it is not acidic enough to react with it. f) Weak Acidic Compounds (AW) Compounds in this group are more resistant proton donors. but. e) Strong Acidic Compounds (AS) Compounds in this group can easily donate protons. h) Miscellaneous Neutral Compounds (NM) Compounds in this group contain sulfur or nitrogen and they undergo hydrolysis and reduction when subjected to heat. 2. The litmus is unchanged. c) Water-soluble Neutral (SN) Compounds in this group are partially polar so they are soluble in both water and ether. g) Basic Compounds (B) Compounds in this group are good electron pair donors. Complete the diagram. They are good electron pair donors and they turn red litmus to blue.Compounds in this group are partially polar so they are soluble in both water and ether. They are soluble in 5% NaOH and 5% NaHCO 3 which produces water-soluble salts. d) Ether-insoluble (S2) Compounds in this group are very polar which makes them soluble in water but insoluble in ether. They form hydroxide anions in aqueous solution and they react with acid to form salts. They are predominantly nonpolar so they are insoluble in water. They are unsaturated and are easily sulfonated. They are predominantly nonpolar so they are insoluble in water. j) Inert Compounds (I) Compounds in this group do not undergo sulfonation. [Refer to diagram above] . i) Neutral Compounds (N) Compounds in this group contain functional groups with oxygen but without sulfur or nitrogen.
ketones.and triaryl amines. secondary. enols. hydrazines.g. sulfonic acids. aldehyde. amides. nitriles polycarboxylic acids. ammonium salts. aromatic . amine salts. anhydrides. phenols with electron withdrawing groups in AW phenol E-/α-naphthol B aniline ortho and/or para position/s phenols. di. primary and secondary nitro compounds. aldehydes. alcohols. sulfonamides of primary amines primary. metal salts of carboxylic acids. tertiary amines except di.Table 2: Solubility Classification Class SA Sample none Other Functional Groups Present monofunctional polar compounds (up to about five carbons) SB methylamine* e. phenols substituted with polyhalide nitro group and aldehyde groups.g. S2 alanine ester. carboxylic acids monofunctional polar compounds (up to about five carbons) SN ethylacetate e. N. amines monofunctional polar compounds (up to about five carbons) e. ketone. amides.g. alcohol. sulfanomides of secondary amines.N-dialkylNM benzamide carboxamides nitriles. aromatic nitro N none compounds neutral polar compounds (most containing oxygen). ethers. esters.and polyfunctional compounds including sugars. AS benzoic acid salicylic acid sulfanilic acid polyhydric alcohols carboxylic acids. unsaturated I chlorobenzene hydrocarbons alkyl and aryl halides. amino acids.
molecular structure. saturated hydrocarbons. VI.cyclohexane hexane V. 3rd Edition by Louis Feiser Modern Experimental Organic Chemistry. 2nd Edition by Paula Yurkanis Bruice Exploring Life through Science: Chemistry by Aristea Bayquen Chemistry: the Central Science. acidity and basicity. diaryl ether The solubility of compounds depends on different factors such as polarity. intermolecular forces of attraction. It is recommended that the students be extra careful in handling the reagents so as to avoid contamination because this may lead to different or erroneous results. molecular weight. 9th Edition by Theodore Brown Chemistry by Estrella Mendoza Organic Experiments. Contributions of Members 1) Albarico -Introduction to Discussion -Typing and Printing 2) Bojare -Diagram -Pictures of Results 3) Hernendez -Answers to Guide Questions -Conclusion and Recommendations . 4th Edition by Royston Roberts VII. References: The Essentials of Organic Chemistry. Conclusions and Recommendations hydrocarbons. Solvation is mainly governed by the “like dissolves like” principle which means higher solubility between polar solutes and solvents and nonpolar solutes and solvents.