A Comparison of Organic and Inorganic Compounds

Objectives 1. To sharpen powers of observation. 2. To review the relationships between molecular structure and chemical and physical properties. 3. To classify compounds as organic or inorganic on the basis of observations of chemical and physical properties. Background You are to make a preliminary investigation of two unknown compounds: a solid and a liquid. By means of the simple qualitative tests suggested in this exercise, you can find out whether a compound is organic or inorganic. (Organic compounds are those containing C, H, and other elements.) In addition, for organic compounds, you can determine whether or not the compound is polar. Inorganic compounds in this experiment are ionic compounds (water being the exception). This ionic quality makes them relatively nonvolatile solids with a disposition toward water solubility. There are exceptions, of course, but as a reasonable first assumption, any water-soluble, high-melting compound that will neither char nor ignite and burn completely away is probably both ionic and inorganic. Organic compounds, by contrast, characteristically char or burn. If they contain no metal atoms, they ignite completely, leaving no residue. Most of them are insoluble in water but dissolve readily in organic solvents such as dichloromethane. Organic compounds tend to boil or melt easily, and they have odors. The experienced chemist can record enough significant observations in a simple preliminary analysis to outline a direct and fruitful approach to the identification of a compound. See how much you can learn about the unknowns issued to you. Record all observations no matter how trivialthere is a logical explanation for all physical and chemical properties. You are encouraged to go beyond the minimum investigation described. But be sure to ask the lab instructors advice before doing sosometimes seemingly simple operations can become safety hazards. Procedure Safety considerations Many of the compounds in this experiment have strong odors--use caution when smelling them. Keep all samples away from flames unless testing small amounts for behavior when heated. Do not breathe large amounts of dichloromethane vapors. Do not add water to glacial acetic acid (add the acid to the water). Place all discards in waste bottle in hood. Use small amounts of chemicals for this experiment. Knowns and Unknowns Obtain a liquid and a solid unknown and record their numbers. Four steps are outlined. Reference compounds are provided for the running of control tests when you are uncertain of an interpretation. For each unknown compound, select two like-

appearing reference compounds, one organic and the other inorganic. Using these as controls, run parallel tests with them and your unknown. Make careful comparative observations. Part 1. Physical Properties Physical state: Inorganic salts tend to be dense and granular. Fluffy powders, fine needles, flakes, or plates suggest an organic nature. Very few inorganic compounds are liquids. Color: Many ions have characteristic colors, like the purple of MnO , and the blue of Cu . Color in an organic system implies the existence of highly delocalized electrons, usually caused by alternating single and double bonds. Sometimes, color is due to the presence of impurities. If it diminishes or disappears upon distillation or recrystallization, colored impurities are implicated. The history of a substance and its source can be very helpful in accounting for both color and odor. Odor: Waft the vapors toward your nose carefully and from a safe distance at first. The volatile organic compounds generally have characteristic odors while inorganic salts do not. Of course, the presence of volatile impurities can be deceptive, but you may assume that you were issued pure compounds. If time permits, check the spectrum of odors offered by this list of common organic solvents. Reference liquids: glacial acetic acid acetone 1-butanol dimethyl sulfoxide ethyl alcohol toluene dichloromethane Reference solids: salicylic acid potassium bromide Part 2. The Ignition Test For a solid: Apply a gentle flame to the bottom of a crucible cover containing a small portion (the size of a pea) of your compound. For a liquid: Apply a gentle flame from the top of a crucible cover containing a few drops of your compound to start the ignition (if you apply the flame from the bottom of the crucible cover, the liquid may just evaporate). Does it melt? Burn? Char? If it burns, note the color of the flame and the odor of the combustion products. Was the flame sooty? Intensify the heating (if no change, heat from the top). Charring due to the presence of carbon will burn away when a red heat is attained. If a residue refuses to ignite away, it is most probably a metallic salt of an organic compound. If a residue remains, allow it to cool, add a drop of deionized water, and test its reaction to red and to blue litmus paper. If the solution is alkaline, a group I or II metal is likely. Record all observations. Are there subtle changes in form or color? Is there an explosive property indicated? Does the residue appear glassy? Part 3. Solubility in Water and Dichloromethane Water is the most common solvent for ionic compounds. Most organic compounds are insoluble in water. Many organic solvents will dissolve most organic compounds ether is often used, but is very flammable and also toxic. We will substitute dichloromethane (also toxic, but not flammable). Unfortunately, many common organic compounds (alcohol, sugar, amino acids, certain vitamins, and many small molecules
2+ 4 -

containing less than 6 carbons and one functional group) have solubility characteristics more like inorganic compounds than organic ones! To 3 ml of water in a test tube add 0.1 g of a solid or 0.2 ml (2-3 drops) of a liquid. Agitate gently while watching for evidence of dissolution like wavy lines, color changes, or an evolution of heat. If the compound dissolves completely, and the ignition test has indicated an organic compound, you can assume that you have one of the common exceptions to the rule listed above. Water solubility of an organic compound indicates polarity. However, not all polar compounds are water soluble. If the unknown is inorganic and soluble under these circumstances, it could be a salt containing NO , C H O , Na , K , or NH . Test the solubility in dichloromethane, using the same amounts. Inorganic compounds are almost always insoluble in dichloromethane. Most organic compounds will be soluble (exceptions noted above). Part 4. Acidity or Basicity Moisten a strip of red litmus paper with deionized water and place a drop (or single crystal) or the unknown on it. If a blue color develops around the site of the addition, a basic compound is indicated. If red litmus gave a negative test, try the same with blue litmus paper. Organic salts, as well as any salt formed from a strong acid and a weak base, will turn moist blue litmus to red. Waste Handling Discard all waste in the waste container. Any unused portion of your unknown should be emptied in the waste container in the hood before returning the empty vial to the supply cart.
4 + + 3 2 3 2 +

Report Sheet: Inorganic vs. Organic Compounds

Name__________________________ Liquid Unknown No _______ Solid Unknown No _______

Liquid Unknown: Physical Properties Physical state: Color: Odor: Other: Ignition Characteristics: Solubility in water: in dichloromethane: Acidity or Basicity: Conclusion Is the compound organic or inorganic? What is the most convincing evidence to support your claim? If organic, is it polar or nonpolar? Solid Unknown Physical Properties Physical state: Color: Odor: Other: Ignition Characteristics:

Solubility In water: in dichloromethane: Acidity or Basicity: Conclusion Is the compound organic or inorganic? What is the most convincing evidence to support your claim? If organic, is it polar or nonpolar? Questions Use these eight compounds to find answers to questions 1 and 2. A. ethanol, CH CH OH B. sodium carbonate, Na CO C. toluene, C H CH
6 5 2 3 3 2 3

E. potassium benzoate, KC H CO F. glucose, C H O

6 12 6 5

G. ammonium sulfate, (NH ) SO H. octanoic acid, C H CO H

8 17 2 4 2

D. sodium hydroxide, Na(OH)

1. Which of the compounds are water soluble (there are 6)? 2. Which are soluble in dichloromethane (there are 4; Hint: see part 3)? 3. Look up the melting point of these three compounds: ethanol_____________________ sodium carbonate______________________ octanoic acid ________________ ammonium sulfate______________________ 4. Look up the boiling point of these three compounds: ethanol_____________________ sodium carbonate______________________ octanoic acid ________________ ammonium sulfate______________________ 5. How do the melting and boiling points of organic and inorganic compounds compare? What intermolecular forces account for this?