This action might not be possible to undo. Are you sure you want to continue?
K. Manlangit, J. Manuel, S.F. Manugas, J. Ongsitco, M.A. Pasciolco* Faculty of Pharmacy, University of Santo Tomas, 2010
Abstract Carboxylic acid and derivatives are a type of carbonyl group that contains a carbon doublebonded to oxygen. These compounds have a common structural feature which is they contain an acyl group bonded to an electronegative atom or substituent that can act as a leaving group. The experiment¶s objectives are to determine the reactivities of carboxylic acid derivatives and to distinguish carboxylic acid derivatives using several classification tests. The reactions involved in each test are explained through chemical equations and mechanisms. To accomplish the objectives of the experiment, the tests done were the hydrolysis, alcoholysis, aminolysis and hydroxamic acid test. Those that give positive results to the test inferred that carboxylic acid is present. Ethyl acetate and acetamide was observed to possess a deep burgundy discoloration. It is important to use a clean and dry test tube because a little water can react to the samples which may give the experiment unnecessary or unwanted results.
Introduction Carboxylic acids and their derivatives are the most abundant of all organic compounds in living organisms and in laboratory. The most common derivatives of carboxylic acids are acyl halides, acid anhydrides, esters, and amides. They contain acyl group attached to a nucleophilic molecule that replaced the -OH group of a carboxylic acid. Carboxylic acids and their derivatives are involved in many industrial processes and most biological pathways (1). Acyl halides are used as a starting material for synthesis due to its reactivity. Amides, like acids and esters, are abundant in living organismsproteins, nucleic acids, and many pharmaceuticals have amide functional group (2). All carboxylic acid derivatives yield the parent carboxylic acid upon reaction with water. Furthermore, one derivative can be converted into another, provided the former is more reactive than the latter (3). Carboxylic acid derivatives react with the same mechanism the nucleophile attacks the carbonyl carbon, forming an unstable tetrahedral intermediate, which modifies a carboxylic acid derivative by eliminating the weakest base. The types of nucleophilic acyl substitution that a carboxylic acid derivative undergoes are hydrolysis, aminolysis and alcoholysis (4). The experiment aimed to differentiate the reactivities of carboxylic acid derivatives and to distinguish it using classification tests. It also aimed to explain through chemical equation and mechanisms the reactions involved in each tests.
Hydrolysis of Acid Derivatives Acid Halides and Acid Anhydrides In a test tube.2 mL of acid halide or acid anhydride sample was placed in another test tube. Amides In a test tube. 1 mL of 2% AgNO was added to the first test tube while 1mL of saturated NaHCO3 was added to the 2nd portion.5 mL of ethanol. Then 0. 1 mL of water was placed and then 10 drops of the sample was cautiously added dropwise. Results observed from the hydrolysis of acid derivatives. 2 mL of 25% NaOH was added. Aminolysis: Anilide Formation Few drops of acetyl chloride or acetic anhydride sample was added to 0. 2mL of 20%NaOH was added. The mixture was transferred to a new test tube with 5ml of water. If color other than yellow is obtained the test cannot be use. B. The mixture was then neutralized with 10%HCl. The color produced when 1 drop of 5%FeCl3 solution is added was noted. . D.Methodology A. 1 mL of benzanamide was treated with 5 mL of 10% NaOH and heated to boiling. Hydroxamic Acid Test Preliminary test: Two drops of the sample was mixed with 1mL of 95% ethanol and 1 M HCl. Results obtained from Alcoholysis were tabulated as shown in table 2. 1 mL of water and 0. It was the cooled and combined with 1 mL of 5%FeCl3. Alcoholysis Acetic acid Acetyl chloride Observations Plastic balloon-like odor Fruity odor Table 2. Alcoholysis: Schotten-Baumann Reaction A mixture of 10 drops of acetic acid. 2 drops of the sample was added to 2 mL of alcoholic NH2OHCl and 1 mL KOH. Results observed from alcoholysis of acetic acid and acetyl chloride. The test tube was stopped with a cork or parafilm and the mixture was shook for several times. Otherwise. The reaction of the gas evolved was tested by holding a piece of moist red litmus paper over test tube during heating. C. The mixture was heated in a boiling water bath for 2 minutes. Results Results obtained from the Hydrolysis of Acid Derivatives were tabulated as shown in table 1.5mL aniline. The resulting mixture was divided into two portions. it is conducted as follows: In another test tube. Hydrolysis of Acid Derivatives Acyl Halides and acid anhydrides Acetyl chloride Acetic anhydride Esters Ethyl acetate Amides Benzamide Plastic balloon-like odor Red to Blue litmus paper (Base) Observations White precipitate with evolution of gas No precipitate with evolution of gas Table 1. The mouth of the test tube was covered with marble and heated in a boiling water bath for 5mins. Esters In 1 mL of ethyl acetate. 1 mL ethanol and 5 drops of concentrated H2SO4 was warmed over a water bath for 2 mins.
An aqueous base. . Results obtained from Hydroxamic Acid Test as shown in table 4. the parent carboxylic acid. aminolysis and alcoholysis and using the gathered positive result. I can say that from the points discussed. The resulting vapor from the reaction upon testing with moist litmus paper was basic due to the basic nature of amine (NH3) (6). It can be concluded from the experiment that carboxylic acid and derivatives can be classified by different classification tests. Table 3. Results observed from the aminolysis of acetyl chloride and acetic anhydride. The gas that evolved during effervescence of the addition of 2% AgNO3 and saturated NaHCO3 in acetyl chloride was due to the evolution of CO2 gas (5). the presence of the particular carboxylic acid derivatives can be determined. a yellow coloration of the resulting mixture during the preliminary test proved the enolic character of the mixture. In the hydroxamic acid test. Ethyl acetate and acetamide were converted to hydroxamic acid upon heating with NH2OHCl. White precipitate was also formed due to the presence of anilide in the mixture which was yield upon addition of water. a warming effect was observed due to exothermal reaction and formation of the acetic acid. the formation of the oily layer was the result of the difference in density and solubility of the compounds.Results obtained from Aminolysis were tabulated as shown in table 3. 25 % NaOH was used to hydrolyze ethyl acetate yielding acetic acid with alcohol which gives a plastic balloon-like odor to the sample. Aminolysis Acetyl chloride Acetic anhydride Observations Yellow oily layer Whitish-yellow precipitate Benzamide yields ethanoic acid plus amine upon heating in 5 mL of 10% NaOH solution. In alcoholysis. Hydroxamic Acid Test Preliminary Test Observations Ethyl acetate and acetamide turned into a yellow solution Deep burgundy discoloration Deep burgundy discoloration Ethyl acetate Acetamide Table 4. Results observed from the Hydroxamic acid test of ethyl acetate and acetamide. In aminolysis. the experiment successfully met its objectives. The types of nucleophilic acyl substitution that a carboxylic acid derivative undergo are hydrolysis. Discussion In the hydrolysis of acyl halides and acid anhydrides. acetyl chloride and acetic anhydride upon reaction with ethanol and H2SO4 formed an ester which gave the agreeable odor of the mixture. The deep burgundy discoloration of ethyl acetate and acetamide was obtained from the reaction of hydroxamic acid with FeCl3. RCONH2 + NaOH ---> RCOO-Na+ + NH3.
al. Quezon City. de Guia R. Australia (5) Pavia. Australia (6) http://www. Philippines (4) Landgrebe. Introduction to Organic Chemistry Laboratory Techniques Microscale rd Approach (3 ed.chemistry.html . M.A. et al. V.chemistry. 2005.T. J. 2009.. Fundamentals of Organic Chemistry. J.Australia (2) http://www.html (3) Bayquen A.ca/~chem2ob3/2004labm anual/stuff_2003/2003_exp4 . Brooks Cole Publishing Company.ca/~chem2o6/labmanual/ expt9/2o6exp9..mcmas ter. Laboratory Manual in Organic Chemistry. Et.. Brooks Cole Publishing Company. Brooks Cole Publishing Company. C&E Publishing. Inc. Lampman.). Theory and practice in the organic laboratory with micro-scale and standard scale experiments (5th ed.). Cruz C. 2010.References (1) McMurry.mcmas ter.
This action might not be possible to undo. Are you sure you want to continue?
We've moved you to where you read on your other device.
Get the full title to continue reading from where you left off, or restart the preview.