Department of Chemical Engineering

School of Engineering and Architecture

Saint Louis University

LABORATORY REPORT EVALUATION SHEET

Laboratory Course: Organic Chemistry Schedule: 1:30-4:30 MW

Experimental Number: 14
Experiment Title: ESTERS
Group Number: 2
Group Members: Bustillo, Rexel Date Performed:
Corpuz, Jonathan Date Submitted: 12/04/19
Bohol, Jolina
Cruz, Maple Cae
Dial, Katherine
Evangelista, Alesandra

TOTAL
CONTENTS REMARKS SCORE
POINTS

I. Objective 5

II. Theoretical background 15

III. Materials:
a. Drawing/ Illustration of
10
Set-up
b. Classification and Uses
IV. Methodology/ Procedure 10

V. Data and Results 15

VI. Analysis of Results 15

VII. Conclusion and

10
Recommendation
VIII. Appendices:
a. Definition of Terms
b. Documentation
10
c. Computation
d. Answers to Questions/
Problems
IX. Bibliography/ references 5

X. Format and Neatness 5

TOTAL POINTS: 100 SCORE:

Evaluated by: Date:

 Department of Chemical Engineering
School of Engineering and Architecture
Saint Louis University

I. OBJECTIVE
This experiment aims to discuss the methods and equations for
preparing esters with their uses.
II. THEORETICAL BACKGROUND

Esters are any of a class of organic compounds that react with water to produce alcohols
and organic or inorganic acids. Esters derived from carboxylic acids are the most common. The

term ester was introduced in the first half of the 19th century by German chemist Leopold
Gmelin. Esters with a formula of RCOOR′ (R and R′ are any organic combining groups), are
commonly prepared by reaction of carboxylic acids and alcohols in the presence of hydrochloric
acid or sulfuric acid, a process called esterification. In the reaction the hydroxyl group (OH) of
the carboxylic acid is replaced by the alkoxy group (R′O) of the alcohol.

Fischer esterification is characterized by the combining of an alcohol and an acid (with acid
catalysis) to yield an ester plus water.

The reverse of the esterification reaction is an example of hydrolysis. Esters may also be
obtained by reaction of acid halides or acid anhydrides with alcohols or by reaction of salts of
carboxylic acids with alkyl halides. One ester may be converted to another ester by reaction The
hydrolysis of esters in the presence of alkalies, a reaction called saponification, is utilized in the
preparation of soaps from fats and oils and is also used for the quantitative estimation of esters.
Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant
odours, slightly soluble in water. Many are responsible for the fragrance and flavour of flowers
and fruits; for example, isopentyl acetate is present in bananas, methyl salicylate in wintergreen,
and ethyl butyrate in pineapples. These and other volatile esters with characteristic odours are
used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents
for lacquers, paints, and varnishes; for this purpose, large quantities of ethyl acetate and butyl
acetate are commercially produced. Waxes secreted by animals and plants are esters formed
from long-chain carboxylic acids and long-chain alcohols. Fats and oils are esters of long-chain
carboxylic acids and glycerol.

Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include
many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under
the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as
textile fibres sold as Terylene, Fortrel, and Dacron.
 Department of Chemical Engineering
School of Engineering and Architecture
Saint Louis University

III. MATERIALS
A. SET-UP
a. Aspirin

B. CLASSIFICATION AND USES

IV. METHODOLOGGY/PROCEDURE
A. Aspirin
Mix 1 g of salicylic acid with 2 ml of acetic anhydride in an
Erlenmeyer flask. Then add conc. Sulfuric acid drop by drop until the
reaction mixture becomes warm. Next is heat the solution in a water
bath at 40°C for 5 minutes in order to complete the reaction. After
heating, cool the flask and add 20 ml of water stir and filter. Dry the
product and weigh and calculate the percent yield. Finally, test the
aspirin by getting a pinch of the powder in a test tube and add an equal
amount of sodium bicarbonate and add 5 ml of water. Note for the
result.
B. Oil of Wintergreen
In a test tube put a 0.20 g of salicylic acid and add 1 ml of
concentrated sulfuric acid. Then, put 1 ml of methyl alcohol. Pour the
mixture into a beaker containing 10 ml of water and note the odor.
C. Artificial Flavors
For Banana flavor, take 3 ml of isoamyl alcohol and add 1 ml
glacial acetic acid then add 2 drops of conc. sulfuric acid. Warm gently
and pour into a beaker containing 10 ml of water. Stir well and note the
odor.
For rum flavor, repeat the procedure using ethyl alcohol and
formic acid instead of isoamyl alcohol and glacial acetic acid.
For raspberry flavor, repeat the procedure using isobutyl
alcohol and formic acid instead of isoamyl alcohol and glacial acetic
acid.
 Department of Chemical Engineering
School of Engineering and Architecture
Saint Louis University

D. Odors
For plastic balloon odor, take 3 ml of ethyl alcohol and add 1
ml glacial acetic acid and 2 drops of conc. Sulfuric acid. TheN warm
the solution gently and pour it into a beaker containing 10 ml of ice
water previously made alkaline with sodium carbonate solution. Stir
well and note the odor.
For lacquers and varnish odors, repeat the procedure using
butyl alcohol and acetic acid instead of ethyl alcohol and glacial acetic
acid.
For flower odor, repeat the procedure using benzyl alcohol
and acetic acid instead of ethyl alcohol and glacial acetic acid.
E. Other Methods
From acyl halides (alcoholysis), take a test tube containing 1
ml ethyl alcohol and carefully put 5 drops of acetyl chloride. Stopper
with a cork and shake then note the odor of the product.
From acetic anhydride (acetylation), take a test tube
containing 1 ml ethyl alcohol and put 5 drops of acetic anhydride.
Then, add conc. Sulfuric acid drop by drop until the reaction mixture
becomes warm. Heat the solution in a water bath at 40°C for 5 minutes
in order to complete the reaction. Then, cool the flask and note the
odor of the product.
V. DATA AND RESULTS
A. Aspirin
Chemical Equation C9H8O4
Actual weight of Aspirin obtained 0.9114 grams
Percent yield (show computation) 0.9114
× 100 = 91.14%
1
Aspirin + sodium bicarbonate Aspirin was dissolved
Chemical Equation C9H8O4 + NaHCO3  C9H7O4Na +
H2O + CO2
 Department of Chemical Engineering
School of Engineering and Architecture
Saint Louis University

B. Synthesis of oil of wintergreen

Odor of prepared ester Mint odor
Chemical Equation C7H6O3 + CH3OH  C8H8O3 + H2O

C. And D. Artificial Flavors and Odors

Alcohol and Acid reacted Product Odor and Chemical Equation
Isoamyl alchohol + Acetic acid Banana odor
C5H12O + CH3COOH  C7H14O2
Ethyl Alcohol + Formic Acid Rum odor
C2H5OH + CH2O2  C2H6O2 + H2O
Isobutyl Alcohol + Formic Acid Raspberry odor
C4H9OH + CH2O2  C5H10O2 + H2O
Ethyl Alcohol + Acetic Acid Plastic balloon odor
C2H5OH + CH3COOH  C4H8O2 + H2O
Butyl Alcohol + Acetic Acid Lacquers and varnish odor
C4H9OH + CH3COOH  C6H13O2 + H2O
Benzyl Alcohol + Acetic Acid Flower odor
C7H8O + CH3COOH  C9H10O2 + H2O

E. Other Methods
Sweet smell / Pear odor
Ethyl Alcohol + Acetyl Chloride
C2H5OH + CH3COCl 
CH3COOCH2CH3 + HCl
Ethyl Alcohol + Acetic Anhydride C2H5OH + CH3COOH 
CH3COOC2H5 + H2O

VI. ANALYSIS OF RESULTS

In the experiment, the different artificial flavors and odors were produced
through the reaction of a carboxylic acid and alcohol with the presence of
concentrated sulfuric acid as catalyst. The hydroxyl group (OH) of the carboxylic acids
such as acetic acid for banana flavor, plastic balloon, lacquers and flower odors and formic acid
 Department of Chemical Engineering
School of Engineering and Architecture
Saint Louis University

for rum and raspberry odor were replaced by the alkoxy group (R′O) of the alcohols -- isoamyl,
ethyl,isobutyl,butyl, and benzyl alcohol, to form RCOOR' and water.

Int the preapration of aspirin

Fischer esterification is characterized by the combining of an alcohol and an acid (with acid
catalysis) to yield an ester plus water.

VII. CONCLUSION AND RECOMMENDATION

VIII. APPENDICES
A. DEFINITION OF TERMS
B. DOCUMENTATION
C. COMPUTATION
D. ANSWERS TO QUESTIONSt
IX. REFERENCES