CLASSIFICATION TESTS FOR CARBOXYLIC ACID AND DERIVATIVES ABSTRACT

Carboxylic acids are organic compounds primarily characterized by the occurrence and presence of at least one carboxyl group. The principal feature of carboxylic acid is its acidity, as it is generally more acidic than any other organic compounds containing hydroxyl groups but it is weaker in a different sense. Carboxylic acid derivatives, on the other hand, are organic compounds that are indicated by the incidence of a carbonyl group with an electronegative atom attached to the carbon. On this experiment, one of the chief goals is to distinguish and discern the differences between carboxylic acid derivatives through the classification tests. The classification tests performed and executed by the group include the hydrolysis of acid derivatives, alcoholysis, aminolysis and hydroxamic acid test. These tests yielded results which helped the group to infer in which of the following compounds are carboxylic acid and its derivatives are present. In hydrolysis, both acetyl chloride and acetic anhydride reacted with evolution of gas but only acetyl chloride was observed to have a warming effect with formation of precipitate. Benzamide on the other hand proved to be basic. In alcoholysis, odors of the compounds were their distinguishing characteristics, plastic balloon-like odor for acetic acid and fruity odor for acetyl chloride. Meanwhile, in aminolysis, formation of precipitate on both compounds were clearly evident. In hydroxamic acid test, deep burgundy discoloration on the two compounds were observed, excluding the preliminary test. Lastly, the reactions involved in each classification test were expounded through the chemical equations and mechanisms and the reactivities of these compounds were singled out.

INTRODUCTION
The important classes of organic compounds known as alcohols, phenols, ethers, amines and halides consist of alkyl and/or aryl groups bonded to hydroxyl, alkoxyl, amino and halo substituents respectively. If these same functional groups are attached to an acyl group (RCO) their properties are substantially changed, and they are designated as carboxylic acid derivatives. Carboxylic acids have a hydroxyl group bonded to an acyl group, and their functional derivatives are prepared by replacement of the hydroxyl group with substituents, such as halo, alkoxyl, amino and acyloxy. (http://www2.chemistry.msu.edu/ faculty/reusch/virttxtjml/crbacid2.htm) Carboxylic acid derivatives are group of organic compounds that contains a carbonyl group with the presence of an electronegative atom, either oxygen, nitrogen, or a halogen attached to the carbonyl carbon. This difference in structure leads to a major change in reactivity. The reactions of this group of organic compounds typically involve substitution of the electronegative atom by a nucleophile. (http://

The objectives of the group include the aims to differentiate the reactivities of carboxylic acid derivatives, distinguish carboxylic acid derivatives using classification tests and explain through chemical equations and mechanisms the reactions involved in each test.

Experimental A .Compounds tested

The sample compounds tested for each classification test include a.) acetyl chloride for hydrolysis, alcoholysis and aminolysis, b.) acetic anhydride for hydrolysis and aminolysis, c.) ethyl acetate for hydrolysis and hydroxamic test, d.) acetamide for hydroxamic acid test and lastly, e.) benzamide for hydrolysis.

B. PROCEDURE
1. PREPARATION AND ASSEMBLING OF APPARATUSES The instruments and apparatuses needed by the group were prepared at firsthand, and these include clean test tubes, beaker, parafilm, test tube holder and rack and litmus paper. The reagents necessary for each classification test were also checked.

chemistry2.csudh.edu/rpendarvis/carboxder.htm)

2. HYDROLYSIS of Acyl Halides & Acid Anhydrides 10 drops of the sample compounds namely acetyl chloride and acetic anhydride were separately introduced into a 1 ml of water in a test tube. The resulting mixture of the two compounds were divided into two portions and to the first, drops of 2% AgNO3 were added and into the second portion, drops of saturated NaHCO3 were added. 3. HYDROLYSIS of Esters 1 ml of ethyl acetate was prepared into which 2 ml of 25% NaOH was added. The mouth of the test tube was covered with parafilm and it was heated for 5 mins. After heating, it was then neutralized by adding 10% HCl solution. 4. HYDROLYSIS of Amides A few drops of benzamide was treated with 5 ml of NaOH solution and it was then heated. A piece of moist red litmus paper was then placed over the test tube to test the reaction of the gas that evolved. 5. ALCOHOLYSIS 10 drops of acetic acid was mixed with 1ml of ethanol and 5 drops of concentrated H2SO4 and the mixture was then heated. Meanwhile, the acetyl chloride sample was mixed with few drops of ethanol, water and 20% NaOH solution. The test tube was then covered with parafilm so it could be shaked. 6. AMINOLYSIS Few drops of aniline was added to separate test tubes containing acetyl chloride and acetic anhydride. 5 ml of water was then added to both separate mixtures. 7. HYDROXAMIC ACID TEST Few drops of separate ethyl acetate and acetamide was added with 2 ml of NH2OHHCl and 1 ml of 1M KOH. The mixture was then

derivatives Acyl halides& Acyl Anhydrides Acetyl chloride Acetic anhydride Esters Ethyl acetate Amides Benzamide

Warming effect, formation of white ppt., evolution of gas No warming effect, no ppt. Formed, evolution of gas Plastic balloon-like odor Evolution of gas, Red to Blue litmus paper change (BASIC)

Table 1. Results from Hydrolysis of Acid derivatives

The warming effect observed in hydrolysis of acetyl chloride was due to the exothermal reaction and eventually the formation of the acetic acid, the parent carboxylic acid. 25 % NaOH, which is an aqeous base, was used to hydrolyze ethyl acetate which eventually yielded acetic acid with alcohol and produced a plastic balloon-like odor. Benzamide yields ethanoic acid plus amine upon heating in 5 mL of 10% NaOH solution. The resulting vapor from the reaction upon testing with moist litmus paper was basic duet o the basic nature of amine.
Hydrolysis is the addition of water to form f o r m carboxylic acids. The reaction is seen in Figure 1:

Figure 1. Reaction in Hydrolysis Table 2 shows the results and observations acquired from the alcoholysis test.

heated and cooled afterwards. 1 ml of 5% FeCl 3 was finally added to the mixture. RESULTS AND DISCUSSION Table 1 shows the results and observations acquired from the hydrolysis test. Hydrolysis of Acid Observations

Alcoholysis Observations Acetic acid Plastic balloon-like odor Acetyl chloride Fruity odor Table 2. Results of Alcoholysis The agreeable odor of both mixtures was formed upon the reaction of acetyl chloride and acetic acid with ethanol and H2SO4.

Alcoholysis is the reaction with an alcohol to yield amides. This is seen in the SchottenBaumann reaction, as shown in Figure 2, which involves conversion of acid to acid chloride:

Figure 2. Schotten-Baumann reaction in Alcoholysis

Table 3 shows the results and observations acquired from the aminolysis test. Aminolysis Acetyl chloride Observations Formation of dark red gel-like precipitate Acetic anhydride Formation of dark red gel-like precipitate Table 3. Results from Aminolysis The precipitate formed in aminolysis was due to to the presence of anilide the mixture, which was yielded upon addition of water. In short, aminolysis can be described as the reaction of amines to yield amides.

Table 4 shows the results and observations acquired from the hydroxamic acid test. Hydroxamic Acid Test Ethyl acetate Observations

Deep burgundy discoloration Acetamide Deep burgundy discoloration Table 3. Results from Hydroxamic acid test

The deep burgundy discoloration of the two compounds was brought about by the reaction of hydroxamic acid with FeCl3.

REFERENCES:
[1] Bayquen, Aristea V., et al. (2009). Laboratory Manual in Organic Chemistry. Manila: C&E Publishing Inc. [2] Classification Tests for Carboxylic Acid and Derivatives

http://www.scribd.com/doc/48730739/Classific ation-Tests-for-Carboxylic-Acid-and-Derivatives [3] Classification Tests for Carboxylic Acid

and Derivatives

http://www.scribd.com/doc/45117048/Classific ation-Tests-for-Carboxylic-Acid-and-Derivatives [4] Carboxylic Acids

http://www2.chemistry.msu.edu/ faculty/reusch/virttxtjml/crbacid2.htm [5] Carboxylic Acids and Derivatives http://chemistry2.csudh.edu/rpendarvis/c arboxder.htm