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Chemistry 2412L
Esterification Report Sheet
Name(s): ____________________________________________
Date: _______________________
I. Data and Observations
Tube #
Carboxylic Acid
Alcohol
1
Formic Acid (methanoic acid)
Isobutyl Alcohol
2
Acetic Acid (ethanoic acid)
Amyl (1-pentanol)
3
Acetic Acid (ethanoic acid)
1-octanol
4
Acetic Acid (ethanoic acid)
1-propanol
5
Propanoic Acid
Isobutyl Alcohol
6
Cinnamic Acid
Methanol
7
Cinnamic Acid
Ethanol
8
Salicylic Acid
Methanol
9
____ - 1
____ - 2
10
____ - 1
____ - 2
Note any observations in color of each ester.
Tube #
1
2
3
4
Observations
Scent
Chemistry 2412L
5
6
7
8
9
10
Note which ester you think your unknowns are based strictly on physical appearance and scent
Tube #
Carboxylic Acid
Alcohol
9
____ - 1
____ - 2
10
____ - 1
____ - 2
Name of Ester
II. Reactions
(Draw the reactions taking place in each of the 8 known reactions in this experiment. You do not
need to show a mechanism. Also provide the name of the ester produced for each of the 8 known
reactions)
III. Data Analysis
1. For the reaction in test tube #1 calculate the limiting reagent and the theoretical yield.
Assume that there are 20 drops in 1 mL. Show your work for full credit.
2. Give the structures and names of 5 additional esters, not formed in this experiment, which
could be produced from the carboxylic acids and alcohols used in this experiment.
3. Match the experiments in test tubes 1, 4, and 5 with the 1H-NMR spectra A, B, and C below.
For each 1H-NMR spectrum label which sets of hydrogens in the structure corresponds to
which signal in the spectrum.
Chemistry 2412L
IV. Questions
Chemistry 2412L
1. Esterification is a highly reversible reaction. Which fundamental principle in chemistry
should be utilized to improve the yield of the ester? Give two ways that this can be
accomplished.
2. We know that the esterification reaction is in equilibrium. Does water participate in the
equilibrium constant? Back up your answer with an explanation.
3. What is the purpose of using a saturated sodium chloride solution in this experiment?
4. The esterification mechanism is given below. Use this mechanism to explain the role of
H2SO4 in the first step of the reaction.