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Carboxylic acids are mainly organic compounds containing at least one carboxyl group. Its derivatives are defined as organic compounds with a carbonyl group with an electronegative atom attached to the carbonyl carbon. Acyl halides are the most reactive and amides the least reactive. The reaction of carboxylic acides also yield esters, salts and acyl chlorides.
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Classification Tests for Carboxylic Acid and Derivatives
Carboxylic acids are mainly organic compounds containing at least one carboxyl group. Its derivatives are defined as organic compounds with a carbonyl group with an electronegative atom attached to the carbonyl carbon. Acyl halides are the most reactive and amides the least reactive. The reaction of carboxylic acides also yield esters, salts and acyl chlorides.
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Carboxylic acids are mainly organic compounds containing at least one carboxyl group. Its derivatives are defined as organic compounds with a carbonyl group with an electronegative atom attached to the carbonyl carbon. Acyl halides are the most reactive and amides the least reactive. The reaction of carboxylic acides also yield esters, salts and acyl chlorides.
Copyright:
Attribution Non-Commercial (BY-NC)
Verfügbare Formate
Als DOC, PDF, TXT herunterladen oder online auf Scribd lesen
Classification Tests for Carboxylic Acid and Derivatives
Mary Catherine Sarte, John Emmanuel Sy, Allurie Umel,
Franklin Yap, Mary Christine You Abstract Carboxylic acids are mainly organic compounds containing at least one carboxyl group. Its general formula is represented by the formula R-COOH. Its derivatives, on the other hand, is defined as organic compounds containing a carbonyl group with an electronegative atom (oxygen, nitrogen or halogen) attached to the carbonyl carbon. Among these carboxylic acid derivatives, acyl halides are the most reactive and amides the least. Reactions of carboxylic acides also yield esters, salts and acyl chlorides. The experiment done is to test whether the substance is positive for carboxylic acid and derivatives. The reagents used are acyl chloride representing acyl halides; acetic anhydride representing acid anhydrides; ethyl acetate representing esters and acetanamide and benzamide representing amides. Specific tests were performed to specific compounds. Yielding a positive results indicate the presence of the carboxylic acid group.
was aminolysis: anilide formation. Aminolysis is
Introduction the reaction with ammonia or amine to yield an Carboxylic acids derivatives are simply groups amide. In this case, aniline was the ammonia and of compounds that contain a carbonyl group but anilide, an amide, was produced. Hydroxamic with an electronegative atom attached to the acis test was used for ethyl acetate and carbon. The difference in the structure leads to a acetamide. major change in reactivity. The reactions of these Through this experiment, students are able to groups of compounds involve nucleophilic visualize, through the different reactions, the substitution. Although there are abundant kinds necleophilic acyl substitution reaction for of carboxylic acid derivatives, the experiment carboxylic acids and it derivatives. The different only focuses on the common ones: acid halides, classification tests for such are also observed. acid anhydrides, esters and amides. Carboxylic acids and their derivatives are Experimental usually seen in industrial processes and most A. Hydrolysis of Acid Derivatives biological pathways. Esters can be seen as fats Acyl halides and Acid anhydrides and within the cell membrane. Esters are also 1 ml of water was placed in a test tube. 10 present in pleasant smelling liquids that are drops of the sample, in this case acetyl chloride responsible with the fragrant odor of fruits and and acetic anhydride, was added in a drop wise flowers. Amides are also present in animal manner. A warming effect was noted. The first protein and also in industrial products such as resulting mixture was divided into two portions. nylon. Acid chlorides and acid anhydrides are To the 1st, 1 ml of 2% AgNO3 was added. used in the synthesis of carboxylic derivatives. Precipitation was observed. To the second These are not usually found in nature because of mixture, 1 ml of saturated NaHCO3 was added. its high reactivity property. An evolution of gas was observed. One property of carboxylic acids is that they Esters are acidic. Because of these, carboxylic acids are 2ml of 25% NaOH solution was added to 1 ml mostly made to react with bases such as NaOH to of ethyl acetate. The mouth of the test tube was yield a water soluble metal carboxylates. covered and the test tube was heated in a boiling Carboxylic acids and their derivatives react water bath for about 5 minutes. The mixture was with nucleophiles which yields a formation of then neutralized with 10% HCL solution. With a alcohol. The initially formed intermediate product wafting motion, the odor of the solution was expels one of its substituents which is originally noted. bonded to the carbonyl carbon forming a new Amides carbonyl compound. The reaction is called 1ml of benzamide was treated with 5ml of 10% nucleophilic acyl substitution reaction. NaOH solution. The solution was then heated to The procedure for acyl halides, acid anhydrides, boiling. While heating, the test for the reaction of esters and amides is hydrolysis. Hydrolysis is gas evolution was done by holding a piece of simply the reaction with water to yield a moist red litmus paper over the heated test tube. carboxylic acid. Also for acetyl chloride is B. Alcoholysis: Schotten-Baumann Reaction alcoholysis: Schotten-Bauman Reaction. It is the A mixture of 10 drops of acetic acid, 1ml reaction with an alcohol to yield an ester. The ethanol and 5 drops of conc. was warmed alcohol used here was ethanol. Again for acetyl over a water bath for 2 minutes. The odor of the chloride and acetic anhydride, the reaction used ester formed was noted. In another test tube, a mixture of 0.5ml As said, carboxylic acids and derivatives, when ethanol, 1ml water, and 0.2ml of acyl halide or reacted with a nucleophile, the reaction is termed acid anhydride was prepared. 2ml of 20% NaOH as nucleophilic acyl substitution reaction. It is solution was then added. The test tube was similar with the reaction of aldehydes and covered with paraffin wax and was shook for ketones but their difference is that in the several minutes. An odor of the formed ester and product. An intermediate product normally forms a formation of two layers were noted. and it expels one of its substituents originally C. Aminolysis: Anilide Formation bonded with the carbonyl carbon, leading to a A few drops of acetyl chloride or acetic new carbonyl compound. anhydride was added to 0.5ml of aniline. The The usual nucleophilic acyl substitution reaction mixture was transferred to a new test tube begins with the addition of a polar bond to give containing 5ml water. The formation of a an intermediate, the alkoxide ion. The precipitate was noted. intermediate formed is protonated to give an D. Hydroxamic Acid Test alcohol. In carboxylic acid derivatives, the The preliminary test was done by mixing 2 intermediate forms expels a living group to give a drops of the sample, 1 ml of 95% ethanol and 1M new carbonyl compound. These different HCL. A drop of 5% FeCl3 solution was added to behaviors towards the reactions are because of the mixture and the color produced was noted. If the difference in structure. Carboxylic acid a color other than yellow was obtained, the test derivatives have an acyl carbon bonded to a cannot be used. Otherwise, another test was group –Y that can leave as a stable anion. When conducted as follows: the addition of nucleophile occurs, the group 2 drops of the sample was added to 2ml of leaves and a new carbonyl compound is formed. alcoholic NH2OH HCL and 1ml of KOH. The The difference of carboxylic acid derivative solution was heated in a boiling water bath for 2 substitution and aldehyde addition is that minutes. The mixture was cooled. 1ml of %5 aldehydes don’t have leaving groups, therefore, FeCl3 was then added. A deep burgundy no substitution takes place but only addition. precipitate was observed.
Results and Discussions
A. Hydrolysis of Acid Derivatives With the addition of AgNO3 to acetyl chloride, a white precipitate was formed and there was no evolution of gas. For acetic anhydride, there was The rate of the overall reaction involves the no precipitate but there was an evolution of gas. addition step and the elimination step. But the With ethyl acetate, an alcoholic scent was addition step is usually the rate determining step. observed when added with NaOH and then the The more the electron poor the C=O is, the odor was gone when neutralized with HCL. For more readily it reacts with nucleophiles. Having benzamide, in the addition of NaOH and when the said this, usually acid chlorides are the most mixture was heated, an evolution of gas was reactive compounds because of its noted and the red litmus paper tested turned to electronegative ion, chlorine. Amides, on the blue, indicating that it was a basic solution. other hand are the least reactive compound. B. Alcoholysis: Schotten-Baumann Reaction These differences in reactivity usually result to When 0.5ml of ethanol, 1ml of water and 0.2ml the conversion of a more reactive acid into a less of acetyl chloride was prepared, with the addition reactive one. of 20% NaOH solution, a fruity odor and a Reactions involving carboxylic acid derivatives solution with layers was noted. include hydrolysis, alcoholysis, aminolysis, C. Aminolysis: Anilide Formation reduction and Grignard reaction. When0.5ml of aniline was added to the sample, Hydrolysis is the addition of water to form a white crystalline precipitate was observed, carboxylic acids. This is seen in the reaction: indicating the presence of acetanilide. D. Hydroxamic Acid Test The preliminary test was no longer performed because the reagents used in this experiment were already given. Doing a preliminary test will surely yield a positive result for the two reagents. For the actual test, both ethyl acetate and acetamide yielded a deep burgundy precipitate which was an indication of a positive result. There is an intermediate product in which Pavia D.L., Lampman G.M., Kriz G.S., (2005) undergoes loss of HCL to yield the product. This Intriduction to Oragnic Laboratory Techniques, is seen in esters, amides and acid chlorides. A Small Scale Approach. 2nd ed. Australis: Brokkes/Cole Alcoholysis is the reaction with an alcohol to yield amides. This is seen in acyl chloride http://chemistry2.csudh.edu/rpendarvis/carb reactions. The best known method is the Schotten-Baumann reaction, which involves oxder.html#struct conversion of the acid to the acid chlorides: www.wikipedia.com
Aminolysis is the reaction of amines to yield
amides. The amine used in the experiment is aniline and the product formed was anilide. The reaction is as follows:
Reduction is the reaction with hydride reducing
agent to yield an alcohol. Esters are usually involved here which has a primary alcohol as a product. The reaction is as follows:
Gringard reaction is the reaction of an
organomagnesium reagent to yield an alcohol. Esters are also the ones involved here converting them into tertiary alcohols. The reaction is as follows:
These are the reactions involve in the
experiments for the classification of carboxylic acids and derivatives. Positive observations in these tests are usually in the form of precipitates. Some exhibit evolution of gas.
Refferences
Bayquen A.V., Cruz C., De Guia R., Lampa
F., Pena G., Sarile A., Torres P. (2008) Laboratory Manual in Organic Chemistry. Manila Philippines: UST Publishing House.
McMurry J. (2010) Foundations of Organic Chemistry.