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Andrea Klein, 0892231 Lab 1

Lab 1: Isomers & Carboxylic Acids


Andrea Klein, 0892231
KIN1070
Summer 2014
Danyelle Liddle
June 6, 2014

Andrea Klein, 0892231 Lab 1

Abstract
Esters and carboxylic acids both have acidic properties, and are common compounds
found in biochemistry, yet, have very different components. Experiments were performed by
combining carboxylic acids and alcohols to produce esters, in order to determine differences in
odor. Structural formulas were also recorded for an understanding of the significantly different
molecular composition of each functional group. Carboxylic acids contain a COOH group and
have a sour scent, whereas, esters contain the COOR group and have a slightly sweeter scent.
These results signify the characteristics that make each functional group unique, and how mixing
chemicals together can produce a final product with significantly different properties.
Introduction
In biochemistry, and any biologic science for that matter, there is a presence of
biomolecules, which are made up of proteins, carbohydrates, lipids, and nucleic acids.
Biomolecules can be made up of some or many thousands of atoms and can become very
complex structures. These biomolecules can be classified into hydrocarbons and functional
groups based on their composition and structure. This laboratory focuses on three common
functional groups and their relationship to one another; carboxylic acids, alcohols, and esters.
Esters are products of combining carboxylic acids and alcohols. Carboxylic acids contain a
carbonyl group (C=O) because they are missing an oxygen and hydrogen bond. Alcohols (OH)
are considered to be a hydroxyl group because of the presence of hydrogen and oxygen, whereas,
an ester, consisting of elements from both carboxylic acid and alcohol, is considered to be a
carboxyl group because of their components (OH-C=O). Esters, in their nature, behave as acids
because of the presence of the double bonded carbon and oxygen. The reaction of a carboxylic
acid and an alcohol to form an ester is called a condensation reaction because water is eliminated

Andrea Klein, 0892231 Lab 1

as part of the product. This reaction also requires heat and acid to act as catalysts for the reaction
to occur.
Although esters and carboxylic acids may behave in similar ways, they have very distinct
odors that set them apart from the other. Carboxylic acids have a strong, vinegary odor, whereas,
esters contain a slightly sweeter, more pleasant odor. The purpose of this lab is to understand
similarities and differences between carboxylic acids and esters, as well as, the biochemical
make-up of an ester and, lastly, to apply knowledge from lectures on how to draw and name
alcohol, carboxylic acid, and ester compounds.
Methods
Refer to KIN 1070 lab manual. Lab 1. Summer 2014
Results
The odor of the carboxylic acids were noted to have a vinegary smell. The odor of the
alcohol compounds were noted to smell like permanent markers. Lastly, the odor of the ester
compounds were found to not have much of a difference in smell and a marker odour was
detected in each ester; however some variations existed. Table 1 includes the odors for each
compound. Table 3 was then filled out in order to understand the structural formulas for each
functional group.
Discussion
Upon completing the experiment and wafting each compound to determine each unique
scent, it was clear the distinctions between carboxylic acid and alcohol; based on odor alone. The
distinctions of odor between alcohol and the esters; however, were not so clear, although, a faint

Andrea Klein, 0892231 Lab 1

difference could be identified. The major difference that could be determined from this
experiment was in drawing the structural formulas and identifying the different functional groups
present in each compound. Esters contain the R group from the alcohol and the OC=O from the
carboxylic group, resulting in a loss of water from the alcohol (OH) and H from the carboxylic
acid.
Each alcohol, carboxylic acid, and ester functional group had considerably distinct odors.
For instance, the carboxylic acids had a very strong vinegary scent that was not pleasant, which
is most likely due to their acidic behaviour. The alcohols smelled like permanent markers, didnt
have quite as strong of a smell; however, were also unpleasant. The esters had a hint of fruitiness
to their odor, although, a permanent marker smell was still able to be detected. Among the esters,
it was evident; however, that the odors were not as unpleasant and resembled a sweet scent. The
reaction that took place to produce an ester highlighted the chemical change that took place
between the reactants and the final product; the ester developed different chemical properties that
changed its scent. The reaction that occurred in this experiment is called a condensation (or
dehydration) reaction because a water molecule is lost in the process. The OH from the alcohol
and the O from the carboxylic reaction is eliminated to form the water molecule in the final
product.
Esters are very common compounds that can be found in many items that you would find
at the grocery store. For example, ethyl formate has a rum scent and is found in rum, N-amyl
acetate has a banana- y scent and is the main ester in bananas, N- octyl acetate has an orangy
scent and is found in oranges, methyl butrate has a scent of apples and is found in apples or apple
flavoured foods, lastly, ethyl butrate has a pineapple scent and is also found in pineapples or
pineapple flavoured foods. Esters are important in biochemistry/ metabolism because they are

Andrea Klein, 0892231 Lab 1

the chemical agent that is present in many fruity- tasting and sweet foods. This means that when
determining the characteristics of many fruits, they will have similar properties of an ester
because that is what gives them their flavour and odor. This also indicates that they will have
slightly acidic properties that an ester would have. Knowing this, would potentially provide
insight into the way our body with metabolize and digest fruity foods containing esters.
Two strengths when performing this lab experiment were that we were already familiar
with the topic of esters, carboxylic acids, and alcohols; specifically in naming and drawing each
functional group. Previous knowledge from class lectures could be applied to Table 2 because it
was known that esters contain the functional group COOR, carboxylic acids contain COOH, and
alcohols contain OH functional groups. Another strength when completing this experiment was
that methods and measurements of substances were outlined clearly as to make no mistake which
carboxylic acid was to mix with which alcohol. Instructions were not too difficult and did not
need supervision or professional assistance to carry out the reaction. Safety precautions for
dealing with sulfuric acids, as well as, proper disposal of waste were also clearly outlined in the
lab manual and instructed by lab instructor to ensure safe and proper completion of the lab
experiment. A limitation that occurred while performing the lab experiment was that it was
somewhat hard to waft the vapours of the acids and alcohols while they were sitting under the
fume food. Detecting exact odors from the substances could have error because it could be mixed
from other odors in the fume hood. Another limitation that occurred during the completion of this
laboratory was that there was a large margin for error when manually measuring amounts of each
compound to add in the test tubes. Counting 20 droplets of the liquid substance to add into the
test tube could easily be miss counted resulting in more or less of the substance added. For

Andrea Klein, 0892231 Lab 1

instance, when adding methanoic acid to the first test tube, the individual counting the amount of
drops to add lost count and had to pour the amount back into the beaker and start over again.
Completing this laboratory experiment showcased how chemical reactions can produce
very different products that contain extremely different chemical properties than their reactants.
In this case, an ester was formed, with a sweet odor that is found in many fruits, such as bananas
and oranges, and other fruit flavoured foods and beverages. This ester was produced from a
carboxylic acid, a very strong ordered acidic substance like vinegar and an alcohol, also with a
very strong unpleasant odor. It seems unlikely that these two substances would produce
something that is found in fruity foods. Lastly, drawing and naming each functional groups
further clarified differences that made each group unique. This lab allowed a thorough
understanding of the reaction process required to produce a carboxylic acid ester and its unique
composition and properties.

References
ChemPRIME. (2010, November 4). Esters in foods. Retrieved from
http://wiki.chemprime.chemeddl.org/index.php/Esters_in_Foods
KIN*1070 Class notes. Summer 2014. University of Guelph Humber.
KIN*1070 Laboratory Manual. 2014. Lab 1: Isomers & Carboxylic Acid Esters. University of
Guelph Humber.