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CARBOXYLIC ACIDS AND THEIR DERIVATIVES

I. Introduction
The carboxylic group is one of the most widely occurring functional group in
chemistry. The carboxyl group is a large family of related compounds called Acyl
compounds or the carboxylic acid derivatives. All carboxylic acids are highly
associated with H-bonding. This group contains both a carbonyl group (C=O) and a
hydroxyl group (O-H). Both bonds in isolation, are quite strongly polar. The
distinguish characteristic of carboxylic acids is their acidity. Although weaker than
mineral acids like HCl, carboxylic acids are much more acidic than alcohols because
carboxylate ions are stabilized by resonance.
Carboxylic acids can be transformed into a variety of carboxylic acid
derivatives in which the acid –OH group has been replaced by another substituent.
Some common functional derivatives of carboxylic acids are acid anhydrides, acid
halides, esters, amides and nitriles. Carboxylic acid and its derivatives are
dominated by a single general type of reaction which is the nucleophilic acyl
substitution reaction. These substitution take place by addition of a nucleophile to
the polar carbonyl group of the acid derivative, followed by expulsion of a leaving
group. The most common reactions of carboxylic acid derivatives are substitution by
water, which is hydrolysis, to yield an acid and by an alcohol, which is alcoholysis, to
yield an ester.
II. Objectives
The objectives of the experiment are as follows:
1. To predict the relative acidity and basicity of carboxylic acids and some of its
derivatives.
2. To predict the product of reactions giving rise to carboxylic acids, and the
reactions of carboxylic acids and their derivatives.

crystal visible).IV. *not cloudy *Basic (blue litmus paper remained blue). reaction is characterized when bubble was produced Chemical equations: Salt Hydrolysis Compound C2 H 3 O2 Na + H2O Observations *Sodium acetate was dissolved completely. . benzoic acid formed Chemical equations: Solubility in Aqueous Base Compound Observation Benzoic Acid *Addition of NaOH. reverse reaction Action of sodium Bicarbonate Compound Observation C6 H 5 COOH + NaH 2 CO3 Slow reaction CH 3 COOH + NaH 2 CO3 Fast reaction.homogeneous *addition of HCl.heterogenous (formation of benzoic acid.Homogeneous *addition of HCl. acidic Benzoic acid Heterogeneous *addition of NaOH.reverse reaction. Observation Water Solubility Compound Observation Glacial Acetic Acid Homogeneous.

smell is stronger . smells like plastic Chemical equations: Test for Acetamide TESTS Alkaline Hydrolysis Observation *colorless *vapor: odor like ammonia Acid Hydrolysis *colorless *vapor: odorless Chemical equations: Test for Ester TESTS Ethyl Acetate Odor Plastic balloon Solubility miscible .Test for Acetic Anhydride TESTS OBSERVATIONS Hydrolysis *no change in litmus paper *less smelly than the acetic anhydride sample Alcoholysis *smells stronger (like) than samples *irritates the nose *color changed to transparent *with NaOH.

and sodium hydroxide. Carbonic acid. Acetic acid was to react with sodium bicarbonate. Sodium benzoate and carbonic acid were the products that were formed in the reaction. which is considered as strong base. The first test. pertaining to the solution. The reaction was considered as slow reaction.V. The formation of white crystals were visible which were carried out as benzoic acid. The products that were formed in the reaction of benzoic acid with water were benzoate ion and hydronium ion. The addition of Sodium hydroxide gave the mixture a homogeneous form since the acid was dissolved. Meanwhile. Discussion of Results The experiment was divided into two parts. sodium acetate was dissolved completely. Salt hydrolysis involves sodium acetate and water as reactants. During the reaction. containing two phases. This indicates that the relative strength of acetic acid. The blue litmus paper that was dropped in the test tube remained the color blue. Table 2 shows the solubility of benzoic acid in aqueous base. Since Carbonic acid is unstable. There was a reverse reaction after the addition of hydrochloric acid. The products of the solution were sodium acetate and carbonic acid. it was decomposed to produce water and carbon dioxide. The bubbles that were observed during the test was the formation and the escape of carbon dioxide. which belonged to the properties of the carboxylic derivatives. Table 1 shows the solubility of glacial acetic acid and benzoic acid with water. Table 3 shows the observations that were obtained in the reaction of some acid and sodium bicarbonate. On the other hand. . as unstable compound in nature. which is hydrolysis. shows the observations that were obtained in testing the acetic anhydride. The mixture of benzoic acid in the first test was obtained since it was only the one that has heterogeneous in form. Table 4 shows the observations and results in salt hydrolysis. was decomposed to produce carbon dioxide and water. The reaction of sodium acetate with water yields to acetic acid. The reaction was considered as fast reaction. The mixture was acidic based from the blue litmus paper that turned to red. was about the reaction of acetic anhydride in water. the mixture of benzoic acid with water resulted to a heterogeneous. The mixture of glacial acetic acid and water gave rise to a homogeneous mixture. the reaction of benzoic acid and sodium bicarbonate was as the same as the reaction of acetic acid with sodium bicarbonate. The first part was all about the acidity of carboxylic acids and the second part was all about the properties of the carboxylic derivatives. was weak. which was a base. Table 5. The products of the reaction of glacial acetic acid and water were acetate ion that has negative charge and hydronium ion with positive charge. The solution was clearly visible. which is a weak acid.

test with blue litmus paper. Salt Hydrolysis Hydrolysis Add 1mL acetic anhydride to 5ml water and mix.III. Methodology Place 2ml water in three clean test tubes. Action of Sodium Bicarbonate Shake thoroughly until no more changes occurs. Immerse in ice and add 1mL acetic anhydride drop by drop. Neutralize the solution with 10% NaOH. Place 1mL 10% sodium bicarbonate solution on a watch glass. Record all observations. Dissolve small amount sodium acetate in 2mL water. Test with blue litmus paper. . set aside for the next test. Warm gently and observe the odor of the vapors. alcoholysis Alkaline Hydrolysis Properties of Acid Derivatives Mix and examine. Add one drop of each ethyl acetate and methyl salicylate in 2ml water in separate test tubes. a little powder if solid). Water Solubilty: reaction to Litmus Solubilty in Aqueous base by Salt Formation Acidity of Carboxylic Acids Add 10 drops 40% sodium hydroxide to heterogeneous mixtures. If contents of the tube is heterogeneous. otherwise. Add 1 mL concentrated HCl if acid has dissolved. Addition of little acid to be tested( 6 drops glacial acetic acid or small pinch of benzoic acid or lauric acid). Note the odor. Test the solution with blue litmus paper. Test for acetic anhydride Place 1ml ethyl alcohol in a test tube. Add a little of the pure acid (1 drop if liquid. Mix half a gram acetamide with 5mL NaOH. Shake the test tube and warm gently. Shake and warm. Test for acetamide Acid hydrolysis Odor Esters Solubility and Density Add 2ml dilute sulfuric acid to half gram acetamide. Note and describe the odor of ethyl acetate and methyl salicylate. Note the odor of the vapors.