Systematic identification of organic compounds shriner pdf

 
    Contents
  1. The Systematic Identification of Organic Compounds | Nature
  2. The Systematic Identification of Organic Compound,PDF
  3. The Systematic Identification of Organic Compound,PDF
  4. The Systematic Identification of Organic Compound,PDF

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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Systematic Identification Of Organic Compounds Shriner Pdf

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.

Contributors Each of you will receive two vials: one containing a liquid unknown and one a solid unknown. You will perform a number of experimental procedures on these compounds to gather data. The compounds are part of a finite number of compounds that are listed for you in order of increasing mp and bp. You will determine the actual structure of your unknowns by applying your experimental data to these lists, obtaining a shorter list of possible compounds and performing further experiments to make the final determination. Since each of you has a different compound, you will have to work more independently than before and you will have to evaluate your data and the reliability of your data. Solubility Tests For these tests, you should use approx. The words soluble and insoluble are qualitative, not quantitative. Moreover, some compounds which are not soluble at room temperature, may be soluble at higher temperature.

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. Cool the solution and if it is not basic to pH paper, add additional KOH solution.

If a precipitate has formed, add 5 mL of water and shake vigorously. If the precipitate does not redissolve in the basic solution, it is indicative of a sulfonamide of a secondary amine.

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.

The Systematic Identification of Organic Compounds | Nature

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 Systematic Identification of Organic Compound,PDF

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. Cool the solution and if it is not basic to pH paper, add additional KOH solution.

If a precipitate has formed, add 5 mL of water and shake vigorously. If the precipitate does not redissolve in the basic solution, it is indicative of a sulfonamide of a secondary amine. Formation of a precipitate under acidic conditions suggests that the previously soluble sulfonamide was of a primary amine. If no precipitate has formed, the initial amine could have been tertiary.

Use aniline, N-methylaniline and N,N-dimethylaniline for knowns. If you suspect that you have a carboxylic acid, we will ask you to do a neutralization equivalent. Then submit a preliminary analysis form.

This form is not graded. It gives us a chance to verify that you have not been misled. We will either OK your data or suggest that you repeat certain procedures. At this stage, you should have determined the class of your compound eg, aldehyde, ketone, For the liquid unknown, you will take a micro bp, you will take an IR spectrum using the sandwich cell NaCl method, do solubility tests and, based upon an analysis of this information, do specific functionality tests as described in the manual.

The Systematic Identification of Organic Compound,PDF

Once again, submit a preliminary analysis form. After the preliminary analysis has been confirmed, try to determine the actual structure of your unknown. You will need to make a solid derivative of each unknown to verify your identification of the compounds. For carboxylic acids, the neutralization equivalent may substitute for the derivative.

Possible compounds and their derivatives are listed in the manual and in other texts which are available to you. All tables are listed first by class of compound alcohol, acid, ether, etc.

The Systematic Identification of Organic Compound,PDF

Some headings are more specific such as aliphatic acid, aromatic acid, carboxylic acid, dicarboxylic acid, halogenated acid, , etc. Be certain that you have checked all the tables that pertain to your search. Volume 45 , Issue 6. Please check your email for instructions on resetting your password. If you do not receive an email within 10 minutes, your email address may not be registered, and you may need to create a new Wiley Online Library account.

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