One of the primary tools used to determine the structure of an unknown organic compound are the functional group tests. The simulation allows 15 different tests to be performed. The following process is used to perform a functional group test in the simulation.

  1. Click on the flask and drag a test tube containing an aliquot of the unknown to the stir plate. You can also double-click on the flask. 

  2. Select one of the tests by clicking on the bottle and dragging a pipet to the test tube. You can also double-clock on the reagent bottle. 

  3. The result of the test is shown on the Live Data tab using either a short video or a still picture. Videos are used if information on the process is an important part of the result. The duration of a video clip is no longer than 30 seconds. Results that take longer than 30 seconds are time elapsed. Still pictures are used when there is no change in the solution or for some changes that are essentially instantaneous. Clicking the Save button on a video will save an image to the lab book of what was displayed in the video at the time Save was clicked. 

  4. To perform another test, drag the test tube to the disposal bucket and select another aliquot of the sample.


Listed below are details on the 15 functional group tests.

  1. Bromine Test. A solution containing methylene chloride and unknown is added to a bromine/methylene chloride solution. The persistence of the red bromine color indicates a negative test. The rapid disappearance of the red color indicates an alkene or a ketone with two sites for alpha-bromination. If the color dissipates rapidly and is accompanied by the evolution of gas, the unknown contains an amine. A slower discoloration indicates alpha-bromination of an aldehyde or a ketone. Slow discoloration is also indicative of an activated aromatic ring.
  2. Permanganate Test. A purple permanganate solution is placed in a test tube and unknowns are added directly to the permanganate solution. For solid unknowns, the solid is first dissolved in acetone. If the purple color of the permanganate solution persists, the test is negative. If the solution changes from purple to brown (MnO2), the unknown contains one or more of the following: alkene, primary or secondary alcohol, or an aldehyde.
  3. Jones Test. The unknown is mixed with acetone to produce a saturated solution and then added to the Jones reagent (chromic acid). The persistence of the bright orange color indicates a negative test. A rapid change of the orange color to a light blue color indicates a primary or a secondary alcohol. If the color change takes longer than one or two seconds, the unknown contains an aldehyde.
  4. Lucas Test. Liquid unknowns are placed in the Lucas reagent (ZnCl2 and HCl). If the solution remains clear the test is negative. Tertiary, allylic, and benzylic alcohols, which are six carbons or less, will produce a cloudy solution without heat. Secondary alcohols, which are six carbons or less, will only produce a cloudy solution if heated. Solids are insoluble in the Lucas reagent.
  5. Periodic Acid. The unknown is mixed with H5IO6 and concentrated HNO3 followed by the addition of 5% aqueous AgNO3. The rapid formation of a white precipitate is indicative of vicinal diols. The absence of a white precipitate is a negative test.
  6. Tollens Test. Concentrated aqueous NH3, 5% aqueous AgNO3, and 10% aqueous NaOH are added to a test tube followed by a minimal amount of unknown. The formation of a silver mirror on the test tube wall is a positive test for aldehydes and reducing sugars.
  7. 2,4-Dinitrophenylhydrazine Test. Liquid unknown or a solution containing the solid unknown and ethanol is added to an orange dinitrophenylhydrazine solution. The formation of precipitate ranging in color from red to yellow is a positive test for aldehydes and ketones. Allylic and benzylic alcohols may also give a positive test. Absence of a precipitate is a negative test.
  8. Sodium Bisulfite. Liquid unknown or a solution containing the solid unknown and methylene chloride is added to a saturated solution of aqueous 10% NaHSO3. A white precipitate is a positive test for aldehydes. Alkyl methyl ketones and unhindered cyclic ketones also give positive tests. The absence of a precipitate is a negative test.
  9. Iodoform Test. The unknown and a small amount of 10% aqueous NaOH are heated to 60°C. KI/I2 is then added to the solution followed by the addition NaOH until the solution is again colorless. The appearance of a yellow precipitate is a positive test for methyl ketones. Alcohols which may be oxidized to produce methyl ketones or acetaldehyde also give positive tests. If the solution remains clear, the test is negative.
  10. Sodium Hydroxide. Liquid and solid unknowns are placed in a test tube filled with distilled water. 50% aqueous NaOH is then added to the unknown/water solution. Disappearance of the bilayer or disappearance of the solid are positive tests for carboxylic acids. Phenols also give positive tests. If the appearance does not change on addition of NaOH, the test is negative.
  11. Hydroxamate Test. The unknown, 1 M methanolic hydroxylamine hydrochloride, and 10% methanolic potassium hydroxide are heated at reflux for five minutes. After cooling, the solution is acidified with 5% aqueous HCl. Two or three drops of 5% aqueous FeCl3 are added to this solution. The presence of a red-to-purple color is a positive test for esters, lactones and amides. The absence of color is a negative test.
  12. Hinsberg Test. The unknown, 10% aqueous NaOH, and 30 mg of p-toluenesulfonyl chloride are heated at reflux for three minutes. The resulting mixture is acidified with 10% HCl. Primary amines containing less than seven carbons will not give a precipitate with the original basic mixture, but will form a precipitate when treated with acid. Primary amines having seven carbons or greater will form a white precipitate in both basic mixtures and acidic mixtures. Secondary amines will form a solid in both the basic and acidic mixtures. Liquid tertiary amines will not form a precipitate in either the basic or the acid mixtures. Solid tertiary amines will be unchanged by the basic mixture but will go into solution when treated with acid. Solid unknowns, which are not amines, will remain as solids.
  13. Hydrochloric Acid. Liquid and solid unknowns are placed in a test tube filled with distilled water followed by the addition of 37% aqueous HCl. The disappearance of the bilayer or the disappearance of the solid are positive tests for amines. If the appearance does not change with the addition of HCl, the test is negative.
  14. Sodium Iodide/Acetone Test. A solution is prepared by dissolving the unknown into acetone which is then mixed with the NaI/acetone solution. If a white precipitate appears in the absence of heat, the unknown contains a secondary bromide or a benzylic or allylic chloride or bromide.
  15. Sodium Iodide/Acetone Test + Heat. If the regular NaI/Acetone test is performed and heat is required to get a precipitate, then the unknown contains one or more of the following: secondary bromide, tertiary bromide, primary chloride, or secondary chloride. Caution: halides which give a positive test without heat will also give a positive test with heat. Absence of a precipitate is a negative test.