In the systemic nomenclature of each carboxylic acid. Hydrolysis with aqueous silver nitrate confirmed the presence of acyl chloride by the formation of a silver chloride precipitate. INTRODUCTION Carboxylic acids are generally weak acids which contain a carbonyl group (C=O) attached to it is a hydroxyl group (-OH) also known as carboxyl group [1]. test tube holder and rack. parafilm. acetic acid. Celina Marie Wong Group 10 2F Medical Technology Organic Chemistry Laboratory ABSTRACT Carboxylic acids are organic compounds which contain at least one carboxyl group (-CO2H). esters and amides contain the acyl group (C=O). On the other hand. aminolysis and hydroxamic acid test. 95% ethanol. litmus paper. fats. aniline. Acid anhydrides are commonly used in the preparation of acetate esters. All carboxylic derivatives yield the parent carboxylic acid upon reaction with water [4]. image from Wikipedia image from Wikipedia EXPERIMENTAL A. ester (RCOOR’) and amide (RCONH2) with acyl halides being the most reactive and amides being the least [3]. its name ends with the suffix – oic[3]. Acyl halides are usually used as a starting material for synthesis due to its high reactivity. beaker. while acetamide turned red litmus paper to blue accompanied an ammonia-like odor indicated the presence of amides. alcoholysis. saturated NaHCO3. 5% FeCl3 solution. proteins and drugs like: penicillin and LSD [3]. sample compounds . Chrystel Marlowe Turla. one derivative can be converted into another. Basic Hydroxamic test for ethyl acetate formed hydroxamic acids which was made to react with ferric chloride in acidic environment to form a deep burgundy precipitate indicating an ester. Alcoholysis under acidic condition of acetyl chloride and acetic anhydride yielded an ester. Reaction mechanism is the same for each of its derivatives in which the nucleophile attacks the carbonyl group forming an unstable intermediate. 1M KOH solution. John Henrick Uy. Carl Jerome Umali. glacial acetic acid. 10%. Aminolysis of acetyl chloride and acetic anhydride yielded a white precipitate indicating amide formation. Removal of the weakest base in the compound is a way of stabilizing the newly formed organic compound [1] . 20% and 25% NaOH solution. ethyl acetate representing esters and acetamide representing amides. Compounds tested (or samples used) 2% ethanolic AgNO3. ethyl acetate. Reagents used were acetyl chloride representing acyl halides. Upon hydrolysis of acetyl chloride and ethyl acetate yielded a carboxylic acid. effervescence when sodium bicarbonate was added indicated formation of carboxylic acid. test tubes. Moreover. Carboxylic acid derivatives have a carbonyl group attached to either an electronegative element or a substituent which would determine the reactivity of the compound [2]. Amides are frequently found in nylon. acid anhydrides. Some of its derivatives which include: acyl halides. Basic hydrolysis and acidification of ethyl acetate yielded a carboxylic acid. Nucleophilic acyl substitution is the mechanism involved in this experiment in which involves the replacement of the leaving group by a nucleophile resulting to the formation of carboxylic acid and its derivatives. aspirin and a precursor to various resins. alcoholic NH2OH+HCl. Vienne Czarina Tongco. 1M HCl solution. distinguishing each and explaining through chemical reaction the mechanisms involved in each test of the carboxylic acid derivatives were achieved by the experiment. acid anhydride (RC (O)) 2O). varnishes and paints. acetic acid. Esters which are generally found in essential oils and fruits are typically used in perfumes.CLASSIFICATION TEST FOR CARBOXYLIC ACIDS AND DERIVATIVES Kathleen Adryon Tan. acetic anhydride representing acid anhydrides. Differentiating the reactivity. Bunsen burner. artificial flavorings. Confirmatory test for carboxylic acid derivatives include: hydrolysis. Majority are used in industrial and biological processes. The most common carboxylic acid derivatives are acyl halide (RCOX). concentrated H2SO4. provided the former is more reactive than the latter [4].

Aminolysis: Anilide Formation A few drops of either acetyl chloride or acetic anhydride were added to 0. A leaving group that tends to be displaced faster is a good leaving group. 3. During heating. Esters 2mL of 25% NaOH solution was added to 1mL of ethyl acetate. The mixture was transferred to a test tube which contained 5mL of water. Table 1. Effervescence was due to the evolution of CO2 as indicated by the formation of bubbles when . Evolution of gas was observed. A warming effect of each was noted. a moist red litmus paper was placed above the tube. catalyst was not necessary for the reaction to occur. Procedure 1. Color of the formed precipitate was noted. benzamide/acetamide). The resulting mixtures were divided into two portions. alcoholysis. 1mL of 2% AgNO3 was introduced to the first portion of each. 2mL of alcoholic NH2OH●HCl and 1mL of 1M KOH was added to separate test tubes of 2 drops ethyl acetate and acetamide. Alcoholysis:Schotten-Baumann Rxn 10 drops of acetic acid with 0. During the addition of 2% AgNO3 to the 1st portion of the original test tube. 4. Leaving group is a/an group of atoms/atom that is displaced as stable species taking with it the bonding electrons [3]. acetyl chloride yielded a white precipitate known as AgCl(s). and HCl. Acetyl Warming White Bubbles Chloride effect ppt. Formation of precipitate was observed. and aminolysis. Good leaving groups are usually conjugate base of a strong acid which means it is a weak base [1]. The mouth of the test tube was covered by perforated parafilm and allowed to heat in a boiling water bath for 5 minutes. Hydrolysis of Acid Derivatives Acyl halides and Acid Anhydrides 1mL of water was added to a clean dry test tube. Acetic anhydride did not yield a precipitate due to the absence of halide which would react to Ag+ to form silver halide (refer to table 1. B. reaction with ammonia/amine to yield an amide. formation Acetic Warming Bubbles Anhydride effect formation Due to acetyl chloride and acetic anhydride’s high reactivity.and a loss of H+ to give its parent carboxylic acid. Immersion in a boiling water bath for 2 minutes was done. Hydroxamic Acid Test Preliminary test was done by mixing 1mL of 95% ethanol and 1M HCl to separate test tubes that contained 2 drops of the samples to be used.2mL acetyl chloride and acetic anhydride. Hydrolysis of acetyl chloride by the mechanism nucleophilic acyl substitution is initiated by the attack of water on the carbonyl group of the acyl chloride which forms a tetrahedral intermediate that undergoes elimination of Cl. Typically the leaving group is an anion or a neutral compound.). straightaway carefully add 10 drops of acetyl chloride and acetic anhydride in a dropwise manner. so that its odor can be noted. 1mL of H2O mixture and 2mL 20% NaOH solution were added to each 0. ethyl acetate. If upon addition of 1 drop of 5% FeCl3. Formation of Precipitate was observed. Rule of thumb is the more reactive the derivative will be converted to a less reactive derivative. 1mL of saturated NaHCO3 was introduced to each. reaction with water to yield carboxylic acids. The test tube was wafted. but it undergoes the reaction at a slower rate yielding 2 moles of acetic acid due to the fact that Cl . This reaction is accompanied by a warming effect due to the formation of acetic acid. acetic acid. a color other than yellow will make the test futile. Amides Acetamide was treated with 5mL of 10% NaOH solution and immersed in a boiling water bath. Same principle also applies to acetic anhydride.5mL aniline. For the second portion. Afterwards. acetic anhydride. Carboxylic acid and its derivatives are rank in order of increasing reactivity towards a nucleophile by this arrangement: acid amide< carboxylic acid< ester< acid anhydride< acid halide [2]. afterwards the mixture was allowed to cool.5mL ethanol. the mixture was neutralized with 10% HCl solution. The layers and odor formed by the ester was observed. reaction with alcohol to yield an ester.is a weaker base making it a good leaving group compared to ethyl acetate.(acetyl chloride. Hydrolysis of acyl halide and acid anhydride Sample +H20 +2% AgNO3 +Saturated NaHCO3 2. Same kind of reactions happened in hydrolysis. Results and Discussion Reaction speed of carboxylic acid derivatives is based on the reactivity of a leaving group. 1mL of 5% FeCl3 was introduced in each test tube.

2 layers formed . This process is known as saponification. The appearance of a layer was because of the immiscibility of HCl and the organic layer due to differences in polarity and density of the two. Table 5. Hydrolysis of amide Sample +10% NaOH w/ heating Acetamide Red litmus turned blue Hydrolysis of amides involves the same mechanism which is nucleophilic acyl substitution that yielded ethanoic acid and an amine (NH3). +10% HCl “Vinegar-like” odor Acetic acid Ethyl acetate Hydrolysis of an ester in a basic medium converts an ester in to the carboxylate salt of its parent carboxylic acid and an alcohol from which the ester was formed. Hydrolysis of ester Sample +25% NaOH w/ heating for 5 mins. A large excess of H2O favors the reverse reaction. “Plastic balloon-like” odor. Alcoholysis of acyl halide and acid anhydride Sample Acetyl chloride +Ethanol. Alcoholysis of acetyl chloride and acetic anhydride resulted in the formation of an ester. Esterification of an alcohol using acid chloride is strongly influenced by bulky groups. Moist. red litmus paper turned blue due to the presence of NH3 which is a Lewis base accompanied by an ammonia/amine-like odor. an acid and an alcohol yielded by hydrolysis are extremely soluble in H2O. Bulky (sterically hindered) samples reduce yields. Heating the acid and alcohol in the presence of a small quantity of acid catalyst (concentrated H2SO4) causes ester formation (esterification) along with dehydration. The reaction took a lot of time before it occurred due to the fact that amides are strong bases which make it a poor leaving group.). the only difference is the rate at which the reaction occurs. its parent carboxylic acid (refer to table 2. In the case of acetic anhydride.). In this case. Most of the time. Acetic anhydride White ppt. Amides which do not react with litmus paper will not also give off an amine-like odor (refer to table 3.+ H2O Acetyl chloride White ppt. Table 3. Some amides also yield a precipitate or sometimes a separated liquid phase (a carboxylic acid). Alcoholysis reactions are usually carried out by the presence of NaOH. It took more time for the white precipitate to Table 4. Aminolysis of acyl halide and acid anhydride Sample +aniline. so that it would react with HCl to prevent any unnecessary reactions. an amine. gave the same result which was a white precipitate indicating the formation of anilide upon addition of water (refer to table 5. Chemistry between the two is the same. 20% NaOH “Vinegar-like” odor. The resulting solution was acidified with 10% HCl yielding acetic acid. Table 2. 2 layers formed Fischer Esterification was used to produce ethyl acetate with the use of glacial acetic acid by nucleophilic acyl substitution by ethanol. one half of its molecule acted as a nucleophile.). acetyl chloride is faster due to its good leaving group ability compared to acetic acid.). Formation of heat.). Steric effect slows down the rate of reaction (reactivity: 1°>2°>3° ROH).saturated NaHCO3 was added to the 2nd portion of the original test tube (refer to table 1. Both samples that underwent aminolysis with aniline. evolution of HCl gas. while the other half acted as a leaving group making acetyl chloride an ideal introducers of acyl substituents. ester-like odor and phase separation were signs that the reaction has occurred (refer to table 4.+H2O.

Campbell. Table 6.K.. +1M KOH w/ heating. Peck. R. Inc. Cengage Learning. In this reaction two equivalents of aniline were used up by acetyl chloride...O. [2] Bettelheim. References [1] Davis. Stanley. than in acetyl chloride because of the leaving group reactivity. (2011). Farrell.. Belmonte. Esters react with basic hydroxylamine to yield hydroxamic acid which in turn reacts with acidic FeCl3 to form blue-red/magenta colored ferric hydroxamates (refer to table 6. F. 9th ed. (2010). Laboratory Manual in Organic Chemistry. One equivalent was used to react with the sample. Brown. A. E. Philippines: C & E Publishing. Hydroxamic Test of ester and amide Sample +alcoholic NH2OH●HCl.H. Chemistry. (2007). W. G. . S. Pgs. Singapore: Thomson Learning Asia. M. Belmonte. +5% FeCl3 Ethyl acetate Deep burgundy color Acetamide Only ethyl acetate produced a deep burgundy color due to the fact that it is an ester.. C. CA: Brooks/ Cole. 121123. Cruz. 7th ed. Biochemistry. K.appear in acetic anhydride. [4] Bayquen.A.al. Organic. G. J. Introduction to General.). and the other was used to react with HCl. et. (2009). a minor product of the reaction. CA: Brooks/Cole.L. W. M. and Whitten.. 8th ed.. [3] McMurry. Cengage Learning. Fundamentals of Organic Chemistry.

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Cengage Learning.R. (2012). R. Singapore: Thomson Learning Asia. Stanley. Pgs. E. Campbell.Crouch. G. M. West. 9th ed. C. CA: Brooks/ Cole. S.M.. M. [7] Skoog. (2009).. 8th ed. W. Belmonte... et. Farrell.L. S. Organic. D. F. Biochemistry.A.al. W.. Chen. [8] Bayquen. Holler. Cruz. K.J. 8 ed.H. 57-59 . Introduction to General.C. Singapore: Cengage Learning Asia Pte Ltd.K.. S... Brown. A. F. Laboratory Manual in Organic Chemistry. [2010] Chemistry. Peck. G.References [5] Davis. Inc. Philippines: C & E Publishing...O.. [6] Bettelheim. (2007). D. and Whitten.A. Introduction to th Analytical Chemistry.

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