Name: Group No: II Experiment No: XIV


Objective: To investigate the physical and chemical properties of Carboxylic Acids and the Acid Derivatives. Procedure: [Esterification] Obtain 1mL CH3CH2OH add 10 drops CH3COOH and 5 drops conc. H2SO4


In as watch glass: Mix 0.1g Benzoic acid 5drop methanol and 5 drops conc. H2SO4 and observe [Reaction with FeCl3] Acidify 3mL of 10% NaOH with HOAc. Add Few drops of FeCl3 sol’n and note formation of Fe(OAc)3

Divide sol’n to three Heat the first portion Add few drops of dilute HCl to 2nd portion Untreat 3rd portion (standard) Dissolve 0.2g Benzoic acid in 2mL H2O and heat Add 10% NH3 to basicity. heat [Reactions with dicarboxylic acids] Stain white cloth with iron soak in warm K2C2O4 for 10-15mins Observe .1g benzamide and NaOH. boil off excess ammonia and 2 drops FeCl3 sol’n [Reactions of Acid derivatives] Add 2mL water in test tube and 1mL Acetic Anhydride Agitate and test with litmus In another test tube Mix 0.

2g benzoic acid in 2mL hot water and 10% NH4OH. warmed 0. The solution turns brown and produced orange precipitates Solution turns slightly cloudy The solution is actually color orange.1 BEHAVIOR OF CARBOXYLIC ACIDS AND ITS DERIVATIVES TEST ESTERIFICATION TREATMENT 1mL ethanol + 10 drops HOAc + 5 drops conc. H2SO4. Test tube 1 – heat to boiling Test tube 2 – added few drops of dilute HCl Test tube 3 – untreated Dissolved 0. H2SO4 3mL of 10% NaOH and dilute HOAc and few drops of FeCl3 divided into 3 equal amounts.[Reactions of substituted acids] (Test for tartaric and citric acid) Place 5mL tartaric acid in test tube Add Dilute NaOH sol’n Add KMnO4 to purple and boil Repeat Wth citric acid sol’n Treat with CaCl2 Purple solutions of tartaric and citric Acid and note the behavior. Boiled and added 2 drops ferric chloride OBSERVATION Smells like plastic balloon The solution formed crystal on the watch glass and it smells like a rotten rat. Data and Results: TABLE 14.1 g benzoic acid plus 5 drops methanol + 5 drops conc. After addition of Ferric chloride reddish brown precipitate was formed REACTION WITH FERRIC CHLORIDE .

Discussion: Carboxylic acids are acidic.REACTIONS OF ACID DERIVATIVES 2mL water and 1mL acetic anhydride – agitated and tested with litmus: 0. 0. replacing chloride ions with a carboxylate ion forming sparingly soluble compound. CH3CH2OH. Esterification of carboxylic acids is possible in reaction with alcohol. The acidity of the hydrogen in the carboxyl group accounts for this case.1g benzamide + NaOH. causing the removal of –NH2 group as NH3 and replacing it with –OH attached to the carboxyl group. in this case. indicated by the change of litmus paper to red. indicated by the onset of pleasant odor.1 g benzamine and 5mL of 10% NaOH. which is usually known as acyl-oxygen type of cleavage. whether it’s esterification. . heated The litmus paper turns red indicating that solution is acidic and the solution appears to have two immiscible liquids: Smells like ammonia (strong odor) Ammoniacal odor REACTIONS OF DICARBOXYLIC ACIDS Iron stain on white cloth soaked in a warm solution of K2C2O4. heated for 10-15mins The stain was slightly removed (tartaric) (citric) Brown precipitate was formed and solution has two layers Upper – dark green Lower – light green REACTIONS OF SUBSTITUTED ACIDS Add 5mL tartaric acid solution/citric acid solution and rendered alkaline with NaOH and KMnO4 The solution was golden and yellow and brown precipitate formed. the salts form precipitates with Ferric Chloride because of double displacement reaction. The indication for this reaction is the odor of ammonia upon addition of NaOH to benzamide. esterification takes place in addition with ethanol. Here. or other reactions. The attack of the nucleophilic species. would lead to cleavage of carbon-oxygen bond. After reaction of carboxylic acids to form salts. Acid derivatives containing amino groups attached to the carboxyl groups cab react with strong bases. The carboxyl group with the attached acidic hydrogen is the active site for the reaction of carboxylic acids.

depending upon the solubility of heavy metal oxalates in solutions of alkali oxalates.75x10-5.+ NH3 2CH3COOH 3. In this case. tartaric acid in the experiment hydrated manganese in KMnO4 producing brown precipitate. tartaric acid in the experiment hydrated manganese in KMnO4 producing brown precipitate. Alpha hydroxy polycarboxylic acids such as tartaric and citric acid form soluble colored complex salts with Ferric Chloride. Differentiate citric acid and tartaric acid by reaction with potassium MnO4-. the simplest of all carboxylic acid has pKa = 1. 2. while citric acid turned KMnO4 to K2MnO4 by adding 1e.Dicarboxylic acids such as oxalic acid not only undergo thermal decarboxylation but also forms various metallic salts which has unique properties. oxalic acid in its salt form can remove rust. Though the two acids are both alpha hydroxy polycarboxylic acids. . Acetic MnO4-. Answers to Questions: 1. while citric acid turned KMnO4 to K2MnO4 by adding 1e. Why it is that carboxylic acid is an acid? Carboxylic acids are Brønsted-Lowry acids because they are electron pair acceptors in their –COOH groups. Though the two acids are both alpha hydroxy polycarboxylic acids. The acidity of hydrogen in the –COOH group accounts for the acid-base case of reactions. Oxalic acids can dissolve rust like stain rust in a cloth. Write the chemical reaction involve in the following: Esterification of acetic acid H2SO4 CH3COOH + CH3CH2OH (CH3COO)SO4 + H3O+ Hydrolysis of acetic anhydride CH3COOCOCH3 + H2O Hydrolysis of benzamide C6H5COONH2 + OHC6H5COO. making it relatively strong acid.

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