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Experiment #3
Ester, Ester, read all about it.
Title: Esterification with alcohols and carboxylic acids.
Reference lab: (Please Read)
faculty.eicc.edu/sites/kjohnson/labbook/physicalscience/esters.pdf
Aim: To synthesize several esters and record the various odors.
Background: An ester is an organic compound that is formed when a carboxylic acid reacts
with an alcohol. In addition to an ester being form, water is another product of the reaction.
Esters are a class of compounds widely distributed in nature. They have the general formula:
O
||
R-C-OR
The simple esters tend to have pleasant odors. Food and beverage manufacturers are thoroughly
familiar with these esters and often use them as additives to spruce up the flavor or odor of a
dessert or beverage.( http://www.hartnell.cc.ca.us/faculty/shovde/chem12b/esters.htm)
Synthesis of Esters
Alcohol + Carboxylic Acid
R'OH + RCOOH
Ester + Water
RCOOR' + H2O.
Procedure:
Reagents
Alcohols: Methanol, ethanol and propanol.
Carboxylic acids: Glacial acetic acid (ethanoic), and salicylic acid.
- Distilled water and sulphuric acid.
Esterification Part A: Reaction of each of the 5 alcohols with glacial acetic acid.
1) Place 12 drops of methanol in a dry test tube.
2) Add 4 drops of the acetic acid.
3) Add two drops of concentrated sulphuric acid. (Please be reminded that concentrated acids can
be very dangerous; take the necessary precautions).
4) Heat test tube in boiling water bath for 3 minutes.
5) Add 20 drops of water to the test tube contents.
6) Observe odor by fanning the scent, with your hand, to your nose (cautiously).
7) Repeat the first six steps using the other alcohols, but with the same acetic acid.
Esterification Part B: Reaction of salicylic acid and methanol [Oil of wintergreen]. Will be
demonstrated.
1) Place 0.4 grams of salicylic acid into a clean, dry test tube.
2) Add 12 drops of methanol.
3) Add two drops of concentrated sulphuric acid. (Please be reminded that concentrated acids can
be very dangerous; take the necessary precautions).
4) Heat test tube in boiling water bath for 3 minutes.
5) Add 20 drops of water to the test tube contents.
6) Observe odor by fanning the scent, with your hand, to your nose (cautiously).
Pre-Lab Questions:
1) In general, what purpose does a reflux condenser serve when reaction mixtures are heated?
2) What is Fischer esterification?
3) What is the purpose of the sulphuric acid in the esterification reactions?
4) Look at the naming conventions
Discussion
1) Using the displayed structural formula, draw the reactions for the synthesis of all 4 esters. Be
sure to label the reactants as well as the products. [8 marks]
2) Compare the smells of your synthesized esters with that of the literature. [4 marks]
3) Is this particular type of esterification reversible or not? How do reversible reactions affect the
calculation of the percentage yield? [3 marks]
4) Describe how sulphuric acid performs its role in these esterification reactions. [1 mark]
Conclusion
An appropriate conclusion.