This action might not be possible to undo. Are you sure you want to continue?
Page 1 of 9
Properties of Carboxylic Acids and Esters
Background Carboxylic acids are structurally like aldehydes and ketones in that they contain the carbonyl group. However, an important difference is that carboxylic acids contain a hydroxyl group attached to the carbonyl carbon. —COOH The carboxylic acid group This combination gives the group its most important characteristic; it behaves as an acid. As a family, carboxylic acids are weak acids that ionize only slightly in water. As aqueous solutions, typical carboxylic acids ionize to the extent of only one percent or less.
R—COOH + H2O → R—COO- + H3O+ At equilibrium, most of the acid is present as un-ionized molecules. Dissociation constants, Ka, of carboxylic acids, where R is an alkyl group, are 10-5 or less. Water solubility depends to a large extent on the size of the R-group. Only a few low-molecular-weight acids (up to four carbons) are very soluble in water. Although carboxylic acids are weak, they are capable of reacting with bases stronger than water. Thus while benzoic acid shows limited water solubility, it reacts with sodium hydroxide to form the soluble salt sodium benzoate. (Sodium benzoate is a preservative in soft drinks.) C6H5-COOH + NaOH → C6H5-COO-Na+ + H2O Benzoic acid Sodium benzoate Insoluble Soluble Sodium carbonate, Na2CO3, and sodium bicarbonate, NaHCO3 , solutions can neutralize carboxylic acids also.
and fruits smell the way they do because they contain esters. this process is called saponification. however. water is eliminated. Only those carboxylic acids of low molecular weight have odor at room temperature. catalyzed by an acid catalyst. 3. giving the carboxylic acid and alcohol. while the odor of pineapple is due to the presence of the ester. CH3CH2CH2COOCH2CH3 + NaOH → CH3CH2CH2COO-Na+ + CH3CH2OH Saponification → A distinctive difference between carboxylic acids and esters is in their characteristic odors. 2. To prepare a variety of esters and note their odors. providing odor. the putrid odor of rancid butter is due to the presence of butyric acid. These compounds are used in the food industry as fragrances and flavoring agents. Ester formation is an equilibrium process. they are liquid at room temperature. “soap making. Higher-molecular-weight carboxylic acids form strong hydrogen bonds. ethyl butyrate. Esters. acidity. disagreeable odors. and aroma..Survey of Chemistry I (CH 131) Page 2 of 9 The combination of a carboxylic acid and an alcohol gives an ester. sodium stearate) is a soap. Thus they have high vapor pressure and many molecules can reach our noses. On the other hand. CH3CH2CH2 COOH + CH3CH2OH → H2O + CH3CH2CH2 COOCH2CH3 Butyric acid Ethyl alcohol Ethyl butyrate (Ester) Esterification → ←Hydrolysis The reaction typically gives 60% to 70% of the maximum yield. For example. The reaction is a reversible process. Objectives: 1. Thus few molecules reach our noses. Carboxylic acids are noted for their sour. are solid. it is acid catalyzed. even when the molecular weight is high. do not form hydrogen bonds among themselves. is called hydrolysis. Saponification means. To study the physical and chemical properties of carboxylic acids: solubility. . The base-promoted decomposition of esters yields an alcohol and a salt of the carboxylic acid.g. and have a low vapor pressure. An ester reacting with water.” and the sodium salt of a fatty acid (e. To demonstrate saponification. esters have sweet and pleasant odors often associated with fruits.
As the solution becomes acidic. Of what does it remind you? 2. and mix by sharply tapping the test tube with your finger. Into five clean. Note the odor and compare to the odor of the solution before the addition of base. Does the original odor return? Characteristics of benzoic acid 1. dry small test tube (100 x13 mm) 2 mL of water and 10 drops of glacial acetic acid.1 g of solid carboxylic acid and 10 drops of alcohol according to the scheme in table Note the odor of each reactant. Now add 1 mL of 2 M NaOH to the solution from step no.1 g of benzoic acid for sample size comparison. With your microspatula. continue to add more base (dropwise) until the solution is basic. Cork the test tube and sharply tap it with your finger. 2. dry small test tubes (100 x 13 mm). 2 (above). Remove the cork and determine the pH of the solution as before. By dropwise addition of 3 M HCl. carefully reacidify the solution from step no. 3 (above). Place into a clean. Determine the value of the pH by comparing the color of the pH paper with the chart on the dispenser. 4. Add 5 drops of concentrated sulfuric acid to each test tube and mix the contents thoroughly . Take a glass rod and dip it into the solution. take some sample equivalent to the pre-weighed sample (an exact quantity is not important here). What happens to the solid benzoic acid? Is there any odor? 3. 3. if not basic. what do you observe? Esterification 1. 1 (above). add 2 mL of 2 M NaOH to the solution. You will weigh out 0.Survey of Chemistry I (CH 131) Procedure Carboxylic Acids and Their Salts Characteristics of acetic acid Page 3 of 9 1. Using wide-range indicator paper (pH 1—12). By drop-wise addition of 3 M HCl. cork. Now. carefully reacidify the solution from step no. test the pH of the solution by touching the pH paper with the wet glass rod. test the solution as before with pH paper until the solution tests acid. test as before with pH paper until acidic. How soluble is the benzoic acid? 2. Is there any odor? Mix the solution by sharply tapping the test tube with your finger. Add the solid to a small test tube (100 x 13 mm) along with 2 mL of water. add 10 drops of liquid carboxylic acid or 0. Note its odor by wafting (moving your hand quickly over the open end of the test tube) the vapors toward your nose.
peach. Place the test tubes in a warm water bath at 600C for 15 min. Record on the Data Sheet what has happened to the ester layer (1). After each addition. take a few drops from this top layer and place on a watch glass. Saponification This part of the experiment can be done while the esterification reactions are being heated. Cool the test tube to room temperature by placing it in an ice water bath. Carefully add 6 M HC1 to the solution. Note that there is a layer on top of the water in each test tube. and add 2 mL or water to each. cool. until the solution is acidic. mix the contents and test the solution with pH paper. Heat the contents in a boiling water bath for 30 min. Acids and Alcohols Test tube # 1 2 3 4 5 Page 4 of 9 Carboxylic acid Formic Acetic Acetic Acetic Salicylic Alcohol Isobutyl Benzyl Isopentyl Ethyl Methyl 3. 3. When the solution is acidic. 2. Place into a large test tube (150 x 18 mm) 10 drops of methyl salicylate and 0. Determine the odor of the solution and record your observation on the Data Sheet (2). With a Pasteur pipet. raspberry.Survey of Chemistry I (CH 131) by sharply tapping the test tube with your finger. nail polish remover. Remove the test tubes from the water bath. Match the ester from each test tube with one of the following odors: banana. and wintergreen. what do you observe? What is the name of the compound formed? Answer these questions on .5 mL of 6 M NaOH. 1. Note the odor. 1 mL at a time.
Survey of Chemistry I (CH 131) the Data Sheet (3) Page 5 of 9 .
Survey of Chemistry I (CH 131) Esters Data Sheet NAME: ___________________________ PARTNER: ________________________ Page 6 of 9 DATE: ______________ SECTION: ___________ Characteristics of Acetic Acid Property Odor Water Solution NaOH Solution HCl Solution Solubility pH Characteristics of Benzoic Acid Property Odor Water Solution NaOH Solution HCl Solution Solubility pH .
Survey of Chemistry I (CH 131) Esterification Test Tube 1 2 3 4 5 Acid Formic Acetic Acetic Acetic Salicylic Odor Alcohol Isobutyl Benzyl Isopentyl Ethyl Methyl Odor Ester Page 7 of 9 Odor Saponification 1. What forms on reacidification of the solution? Name that compound. What has happened to the ester layer? 2. Write the chemical equation for the saponification of methyl salicylate. . 4. What has happened to the odor of the ester? 3.
malic acid is present in __________. Look in the Chapter Carboxilic acids and Esters in your textbook ( or consult library. The sting of an ant is caused by _________ acid.Survey of Chemistry I (CH 131) Page 8 of 9 Esters Post-lab Questions NAME: ___________________________ DATE: ______________ SECTION: ___________ 1. an ester of ______________ acid with ____________ acid. Internet ) and find: A) Citric acid is present in __________ . Spinach. molecules that cause ________. ________ and ___________________ when present in the bloodstream in ____________________ levels. inhibits the synthesis of a class of hormones called ___________________. . ___________ acid is a constituent of butterfat. B) Which esters are responsible for the flavor and odor of: -raspberry -apricot -peach -pear -apple C) Aspirin. acetic acid is present in __________ and lactic acid is present in sour __________. Overuse of muscle tissue results in the buildup of __________ acid. How do carboxylic acids and esters differ in their characteristic odors? 2. cabbage and rhubarb contain __________ acid in addition to important vitamins.
Formic acid c. Octyl formate has the flavor of oranges. Write the products from the reaction of benzoic acid and sodium hydroxide.Survey of Chemistry I (CH 131) Page 9 of 9 Esters Pre-lab Assignment NAME: ___________________________ DATE: ______________ SECTION: ___________ 1. What is a soap? . Acetic acid b. Write the structures of the following carboxylic acids: a. Name the alcohol and the carboxylic acid needed to synthesize this ester. 4. Salicylic acid 2. 3.
This action might not be possible to undo. Are you sure you want to continue?
We've moved you to where you read on your other device.
Get the full title to continue reading from where you left off, or restart the preview.