The Systematic Identification of Organic Compounds, 7th Edition (Shriner, R. L.; Hermann, C. K. F.; Morrill, T. C.; Curtin, D. Y.; Fuson, View: PDF | PDF w/ Links. Second edition (Shriner, Ralph L.; Fuson, Reynold C.) View: PDF | PDF w/ Links. Related Content The Systematic Identification of Organic Compounds, 7th Edition (Shriner, R. L.; Hermann, C. K. F.; Morrill, T. C.; Curtin, D. Y.; Fuson, R. C.). View: PDF | PDF w/ Links. Related Content Second edition (Shriner, Ralph L.; Fuson, Reynold C.) The Systematic Identification of Organic Compounds, 7th Edition (Shriner, R. L.; Hermann, C. K. F.; Morrill, T. C.; Curtin, D. Y.; Fuson, R. C.).
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The systematic identification of organic compounds. 4th ed. By Ralph L. Shriner, Reynold C. Fuson, and David Y. Curtin. John Wiley & Sons, Inc., New York. The Systematic Identifiation of Organic Compounds. 4th ed. By Ralph L. Shriner, Reynold C. Fuson, and David Y. Curtin. John Wiley & Sons,. Inc., New York. The Systematic Identification of Organic Compounds. A laboratory manual. Ralph L. Shriner, Reynold C. Fuson, and David Y. Curtin. This is a PDF-only article.
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Use naphthalene for the solid unknown and toluene or xylene for the liquid known. Bromine Test for Unsaturation: Alkenes and alkynes will readily add bromine across the multiple bond unless there are electron withdrawing groups on the multiple bond. One observes the rapid disappearance of the red-brown bromine color.
Aromatic compounds can react with bromine more slowly to give bromine substitution and the formation of HBr, which can sometimes be observed by placing a piece of wet litmus paper over the mouth of the test tube.
Warning: the reagent deteriorates with the formation of HBr so compare the results with a blank. Into a dry, clean test tube, dissolve 0. A positive test requires five or more drops of bromine solution to reach a persistent red-brown color.
Use cyclohexene, octene, or another simple alkene as the known. Use toluene as a known to test for aromaticity. Permanganate Test for Unsaturation Baeyer Test : Aqueous permanganate rapidly oxidizes double and triple bonds while being reduced to MnO2, a brown precipitate. Therefore, disappearance of the purple color and formation of a brown precipitate in minutes is a positive test. However, other compounds react slowly with the reagent including alcohols, aldehydes, phenols, and aromatic amines so interpret your results carefully and look for corroboration from the other tests.
Into a clean test tube, dissolve 0. Use cyclohexene, octene or another simple alkene as the known. Aldehydes and Ketones,4-DNP. Hydrazines such as 2,4-dinitrophenylhydrazine react with the carbonyl group of aldehydes and ketones to give colored precipitates. Normally the reaction is fast but heating may be necessary.
Later, if you wish to make a derivative of your compound, you can use a different 2,4-DNP solution prepared with HCl and methanol.
This usually gives a slower forming precipitate which often provides a derivative of higher purity and higher mp. However, the slow formation of the precipitate is not desirable when looking for a qualitative test signal. The 2,4-DNPs are usually yellow, orange, or red with the deeper color often signifying higher conjugation via double bonds or aromatic rings.
Add 1 mL of the 2,4-DNP test solution and agitate. If a precipitate does not form in 10 minutes, heat on a water or steam bath for a few minutes.
For knowns, use cyclohexanone and benzaldehyde. Warning: a trace of acetone will give a positive test. Tollens Test for Aldehydes and other easily oxidized functional groups. In this test, a stabilized silver ion is reduced to elemental silver by an easily oxidized compound, such as an aldehyde.
The aldehyde is oxidized to a carboxylic acid. A positive test is the formation of a silver mirror as the elemental silver adheres to the wall of the glass tube.
Prepare the Tollens reagent immediately before you plan to use it. NaOH resulting in the formation of solid silver oxide. This produces a silver ammonium complex and is the Tollens solution you will use for the test. Into each of 3 clean, dry test tubes, add 2 mL of the Tollens reagent which is freshly prepared as above.
Dissolve 10 mg of a solid or 1 drop of a liquid unknown in the minimum amount of bis 2-ethoxyethyl ether required to give a clear solution less than 1 mL. Add the unknown solution dropwise, with agitation, to the first test tube. Mix vigorously and allow the solution to stand. Do the same for the known compound. Do not use benzaldehyde for the known.
For the blank, simply add 0. Warning: Wash any minor amounts of residual Tollens reagent into a sink and flush with water. The reagent forms silver fulminate which is very explosive. The test solutions can be disposed of in a jar labeled for that purpose. The silver mirror can usually be washed clean with soapy water and a scrub brush.
If not, see your instructor. Chromic Acid Test for Aldehydes and Alcohols. Dissolve 10 mg of a solid or 1 drop of a liquid unknown in reagent grade acetone in a clean, dry test tube. Add a few drops of chromic acid solution one drop at a time with shaking. Aldehydes and primary and secondary alcohols are oxidized very quickly. Tertiary alcohols are not oxidized. Aliphatic aldehydes are oxidized in less than a minute, aromatic aldehydes take a bit longer.
Since the condition of the acetone is critical, it is wise to carefully run the blank to be certain that the acetone itself is not giving a false positive. Use benzaldehyde and an aliphatic aldehyde for aldehyde knowns and 1- and 2-butanol for alcohol knowns. The chromic acid solution is prepared by dissolving 1. Warning: Cr VI compounds are considered suspect carcinogens and should be handled carefully.
Ferric Hydroxamate Test for Esters.
If you have a carbonyl compound which is not an aldehyde or ketone or carboxylic acid, it could be an ester. If you obtain a color other than yellow, the test cannot be used. Otherwise, the test is conducted as follows: dissolve 50 mg of solid or 2 drops of liquid unknown in 1 mL of 0.
Heat to boiling for minutes, then cool and add 2 mL 1N HCl. The color is due to a complex between the hydroxamic acid and the ferric ion.
A deep burgundy color is positive. Use banana oil or methyl benzoate as knowns. Ferric Chloride test for Phenols.
Just as enols can form colored complexes with ferric ion, phenolate ions can as well. Therefore, this test is designed to convert the weakly acidic phenols to their conjugate base which can then complex with ferric ion.
If the phenol is water soluble, add a few drops of 2. A deep red, green, or blue color is positive. If the phenol is not water soluble, dissolve 20 mg of the solid or 1 drop of the liquid in 1 mL of methylene chloride and add 1 drop of pyridine. An intense color is a positive test. Use phenol as a known.
Not all phenols will give a positive test. Iodoform test for methyl ketones. In this test you will convert the methyl ketone to a triidomethyl ketone which is then cleaved to form iodoform, HCI3, a yellow solid.
Acetone gives a nice positive test so be certain that no traces of acetone are in your glassware. In a large clean test tube or a vial, place mg of a solid or 5 drops of a liquid unknown. Add a total of 3 mL of iodine-potassium iodide solution in six equal portions, stopper and shake well after each addition.
Caution: seal the tube carefully and avoid skin contact with the iodine solution. The color of the iodine will disappear more slowly in the later additions.
The solution should be slightly yellow. Heat if necessary and shake again to force the iodine to react.
When the color is slightly yellow, add water to nearly fill the test tube or container, stopper, and shake vigorously. After standing for 15 minutes, a pale yellow precipitate of iodoform mp oC is a positive test for a methyl ketone. Acetone can be used for the known.
The iodine-potassium iodide solution is prepared from 10 g of iodine and 20 g of potassium iodide in mL of water. Hinsburg Test for Amines. If you have a basic compound which you believe to be an amine, you can corroborate your suspicion and determine if you have a primary, secondary, or tertiary amine using the Hinsberg test. You will react the amine with a sulfonyl chloride forming an insoluble sulfonamide of a primary or secondary amine or the soluble salt of a tertiary amine.
The insoluble sulfonamide of a primary amine will be made soluble in base via removal of the slightly acidic proton on N but that of a secondary amine will not no proton on N to remove. Add mg of a solid or 0. Stopper the tube and shake it for several minutes. Remove the stopper and heat the mixture on a steam bath for 1 minute.