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CLASSIFICATION TESTS FOR CARBOXYLIC ACID AND DERIVATIVES Dan Neil Fabian, Jomarie Galao, Harold Vincent Go,

Patricia Margarita Guadines and Christine Evan Ho Group 4 2F Medical Technology Organic Chemistry Laboratory ABSTRACT
Carboxylic acids are mainly organic compounds containing at least one carboxyl group. Its derivatives are defined as organic compounds containing a carbonyl group with an electronegative atom attached to the carbonyl carbon. Among these carboxylic acid derivatives, acyl halides are the most reactive and amides the least. Reactions of carboxylic acids 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 acetyl chloride representing acyl halides, acetic anhydride representing acid anhydrides, ethyl acetate representing esters, acetamide and benzamide representing amides. The tests done were aminolysis, hydrolysis, alcoholysis, aminolysis and hydroxanamic acid test. Yielding a positive result indicates the presence of the carboxylic acid group.

INTRODUCTION
Carboxylic acid and derivatives are a type of carbonyl group that contains a carbon double-bonded to oxygen. Acyl halides, acid anhydrides, esters and amides are called carboxylic derivatives, and these derivatives contain an acyl group that is attached to a nucleophilic molecule that replaced the OH group of a carboxylic acid. Acyl halides are used as a starting material for synthesis due to its reactivity. Esters and amides are important functional groups in biomolecules like fats and proteins. In general, more reactive acid derivatives easily react to give less reactive derivatives. Their reactivity decreases in the following order: acyl halides, acid anhydrides, esters, amides, and carboxylate ions. Most of these interconversions take place by nucleophilic acyl substation wherein a nucleophile adds to the carbonyl group to give a tetrahedral intermediate, and then a leaving group leaves, regenerating the carbonyl group. Any factors that make the carbonyl group more easily attacked by the nucleophile favor the reaction. Some of these factors include; steric, and electronic factors which affect the reactivity of the acid derivative towards nucleophilic acyl substitution reactions; steric factors wherein unhindered, accessible carbonyl groups react with nucleophiles more readily that sterically hindered groups, and electronic factors wherein strongly polarized acid derivatives are attacked more readily than less polar ones. The types of nucleophilic acyl substation that a carboxyl acid derivative undergoes are hydrolysis, aminolysis and alcoholysis. Hydrolysis involves a reaction with water to yield a carboxylic acid. Alcoholysis involves a reaction with alcohol to yield an ester.

Aminolysis involves a reaction ammonia or amine to yield an amide.

with

EXPERIMENTAL
A. Samples used: Acetyl chloride, Acetyl anhydride, acetate, Acetanamide and Benzamide. B. Procedure 1.B Hydrolysis of Acid Derivatives One 1 mL of water was placed on two separate test tubes, and then cautiously add ten drops of acetyl chloride and acetic anhydride to separate test tubes. The resulting mixtures were divided into two portions. The 1st portion was combined with 1 mL of 2% AgNo3 then observe for precipitation. To the 2nd portion, 1 mL of saturated NaHCO3 was added. The 2nd portion was then noted for evolution of gas. For ethyl acetate, 2 mL of 25% NaOH solution was added to a test tube with 1 mL of the sample. The test tube was then covered with parafilm then heated in a boiling water bath for 5 minutes. After heating, the sample was neutralized with 1% HCl solution. The odor was observed with a wafting motion. For acetamide, 5 mL of 10% NaOH solution was added. The resulting mixture was then heating in a boiling water. A piece of red litmus paper was held at the mouth of the test tube over the water bath then observe for change of color. 2.B Alcoholysis: Schotten-Baumann Reaction A mixture of 10 drops acetic acid, 1 mL ethanol and 5 drops of concentrated H2SO4 was heated over a water bath for 2 minutes. The odor of the resulting ester was noted. Etyl

Another test tube with a mixture of 0.5 mL ethanol, 1 mL water, and 0.2 mL acetyl chloride or acid anhydride was combined with 2 mL 20% NaOH. The test tubes were covered with a parafilm and shaken for several minutes. The odor and formation of two layers were noted. 3.B Aminolysis: Anilide Formation Few drops of acetyl chloride or acetic anhydride sample were added to 0.5 mL aniline. The resulting mixtures were then transferred to a new test tube containing 5 mL water. 4.B Hydroxanamic Acid Test Two drops of the sample was added to 2 mL of alcoholic NH2 OH+Cl and 1 mL KOH. The mixture was heated in water bath for 2 minutes. It was then cooled then combined with 1 mL 5% FeCL3. A deep burgundy was observed.

saturated NaHCO3, there were no precipitates formed however, formation of bubbles was observed in acetic anhydride indicating the presence of carboxylic acid. A thinner-like odor during heating of ethyl acetate confirmed the presence of ester. Red litmus paper turned to blue with an amine-like odor result indicated the presence of an amide during hydrolysis of acetamide which yielded ethanoic acid and amide. B. Alcoholysis: Schotten-Baumann Reaction An ester was formed during alcoholysis of acetyl chloride and acetic anhydride. Both samples have similar mechanism except for the rate of their reaction, in which case acetyl chloride was faster than acetic anhydride. Table 2. Results observed on Alcoholysis of Acetic Acid and Acetyl Chloride Alcoholysis
Acetyl chloride Acetic anhydride

RESULTS AND DISCUSSION


A. Hydrolysis of Acid Derivatives In hydrolysis, acyl halides react with water to yield carboxylic acids. This reaction is a typical nucleophilic acyl substitution process, initiated by the attack of water on the acyl halide carbonyl group. The tetrahedral intermediate undergoes elimination of Cl- and loss of H+ to give the product carboxylic acid and HCl. Table 1. Results on Hydrolysis of Acid Derivatives Hydrolysis
Acid Halides and Anhydrides Acetyl chloride Acetic Anhydride Ester Ethyl Acetate Amide Acetamide

Observations
Vinegar-like odor Plastic balloon-like odor

A vinegar-like odor was observed during alcoholysis of acetyl chlorise. This confirms the presence of ester. In the alcoholysis of acetic anhydride, a plastic balloon-like odor and a formation of two layers were observed which confirmed the presence of ester. C. Aminolysis: Anilide Formation Table 3. Results observed in Aminolysis of Acetic Chloride and Acetic Anhydride

Observations
w/ H2O Warming effect Warming effect w/ 2% AgNO3 White ppt. Formation of bubbles w/ Saturated NaHCO3 Evolution of gas Formation of bubbles

Aminolysis
Acetyl chloride Acetic anhydride

Observations
White crystals White crystals

thinner-like odor Basic (red litmus paper to blue)

Acyl halides react rapidly with ammonia or amines to yield an anilide upon addition of water. Acid anhydride also reacts but it takes a longer span of time. Formation of white precipitate on both sample compounds was due to the presence of anilide in the mixture.

A warming effect was observed in the hydrolysis of both acetyl chloride and acetic anhydride. Upon adding 2% AgNO 3, a white precipitate was formed on acetyl chloride, whereas on acetic anhydride, formation of bubbles was observed. Upon addition of

D. Hydroxanamic Acid Test Both ethyl acetate and acetamide were converted to hydroxanamic acid on being heated with hydroxylamine. The hydroxanamic acid forms strong, colored complex ferric ions which is the deep burgundy discoloration of the compound. Table 4. Results observed on Hydroxanamic Acid test Hydroxanamic Test
Ethyl acetate Acetamide

Observations
Deep burgundy soln Deep burgundy soln

REFERENCES
From books Mcmurry, J. (1990). The Foundations of Organic Chemistry. Philippine Edition. Philippines: MG Reprographics Inc. University of Santo Tomas Faculty of Pharmacy, Organic Chemistry Group. (2009). Laboratory Manual in Organic Chemistry. Quezon City: C&E Publishing, Inc. From the internet Retrieved September 18, 2012, from http://www2.chemistry.msu.edu/faculty/reusch/ VirtTxtJml/crbacid1.html Retrieved September 18, 2012, from http://chemistry2.csudh.edu/rpendarvis/c arbox der.html

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