Академический Документы
Профессиональный Документы
Культура Документы
ABSTRACT
INTRODUCTION
Carbonyl group (C=O) is a functional group that is incorporated by two organic
compounds of aldehydes and ketones (Farmer, Reusch, et.al, 2019). Describing each,
Aldehydes, also called formyl or methonyl groups, are derived from the dehydration of alcohols.
On the other hand, Ketones contain the carbonyl group bonded to two carbon atoms. The
carbon atom of carbonyl group may be occupied by hydrogen, alkyl, or aryl substituents. If at
least 1 one of these substituents is hydrogen, the compound is an aldehyde. However, if neither
is hydrogen, the compound is a ketone. In this experiment, the analysts focused specifically to
aldehydes as they are tasked to perform series of tests starting from its isolation from cinnamon
powder to obtain cinnamaldehyde up to tests that identified its physical and chemical properties.
Cinnamaldehyde, as mentioned to be obtained, is a representative compound that contains
two unsaturated functional groups of aldehyde and carbon-carbon double bond (Module in
Chemistry, 2016). This experiment raises questions regarding the process of the isolation of
cinnamaldehyde and the reason for addition of dichloromethane during the process.
Furthermore, its solubility with water, ether, and ethyl alcohol is examined. This experiment also
addressed questions regarding the mechanism of reaction and the acquired positive results in
identifying its chemical properties by performing Silver Mirror Test, Chromic acid test, Oxidation
Reaction with Potassium Permanganate, Milk Test, Polymerization Reaction, and Addition
Reaction. The purpose of this activity is to give the analysts a more comprehensive knowledge
about the specific functional group. This experiment will give the analysts and manufacturers of
commercial household products (Formaldehyde – used as germicide or insecticed). Medicinally,
aldehydes also perform essential functions in humans such as that of the function of
carbohydrates, which are based on compound containing aldehydes, ketone, and hydroxyl
group. An aldehyde in the retina (retinal), which when combined with protein (opsin) in the retina
of the eye form rhodopsin, which is involved in the process of vision (March & Brown, n.d).
Thus, deeper knowledge of this group will definitely give benefit for assays of new medicine and
even improve old drugs.
EXPERIMENTAL PROCEDURES
B. Solubility test
To evaluate the solubility of the distillate, the analyst gained 1ml of the distillate
and mixed distilled water. The whole procedure was again performed using other
solvent such as Ether and Ethyl alcohol in 2 separates test tubes. Aside from the
stated solvents, the test was repeated with laboratory grade formaldehyde,
acetaldehyde, and benzaldehyde using the same solvents. Observations were
recorded for the analyzation process.
C. Chemical Test
C.1 Oxidation Reaction with Tollen’s test (Silver Mirror test
The group collected 10 drops of distillate and placed it in a clean test tube and
1ml of Tollen’s reagent was added. The test tube was warmed in a water bath at
60oC for 15 minutes. The test was repeated with laboratory grade formaldehyde,
acetaldehyde, and benzaldehyde. Observations were tabulated for further
analyzation.
Distilled Water
ETHER
SAMPLE ETHER
Cinnamaldehyde
Insoluble
Formaldehyde
Immiscible
Acetaldehyde
Immiscible
Benzaldehyde
Insoluble
Petroleum ether is a chemical solvent used in the laboratory. Despite having the word
‘ether’ in its name, petroleum ether is not ether. It is a mixture of various organic compounds
made from carbon and hydrogen, including pentane and hexane. Moreover, it is considered as
a non-polar compound while some ether solvent such as diethyl ether is relatively polar
molecule (Judge, 2018).
ETHYL ALCOHOL
As shown in results above, four out of four of the solvents used were proven to
be miscible in Ethyl Alcohol. As stated in encyclopedia.com, Ethyl Alcohol is
miscible with water, ether, acetone, and most common organic solvents.
Cinnamaldehyde is a polar molecule comprised of carbon, hydrogen, and
oxygen. Therefore dispersion forces, dipole-dipole interaction, and hydrogen
bonding all have the potential to occur between Cinnamaldehyde and another
molecule (pubchem.com) that gives a miscible result when added to Ethyl
Alcohol. Formaldehyde and Acetaldehyde are both organic compound that
results to be miscible in Ethyl Alcohol (pubchem.com). For the last solvent
Benzaldehyde is an organic compound consisting of a benzene ring with a formyl
substituent and it is the simplest aromatic aldehyde (pubchem.com), like 2nd and
3rd solvent, its characteristic of being an organic compound gives the result to be
miscible in Ethyl Alcohol.
C. Chemical Tests
C.1 Oxidation Reaction with Tollen’s Test (Silver Mirror Test)
Cinnamaldehyde
Formaldehyde
Acetaldehyde
Benzaldehyde
Theoretically, all reagents tested were expected to furnish a positive result for the
silver mirror test. This is because the four of them contain an aldehyde as functional
group. Behind the functional group present in them- a) Benzaldehyde is the simplest
aromatic aldehyde b) Cinnamaldehyde contains two unsaturated functional groups of
aldehyde and carbon–carbon double bond. c) Formaldehyde, which is the simplest
aldehyde, has its carbonyl group bonded to two hydrogen atoms. d) While acetaldehyde
is an aldehyde containing a methyl group.
The negative result observed by the researchers in the Tollen’s test for
Formaldehyde, acetaldehyde, and benzaldehyde might be caused by the impurity of the
reagent or failure to accomplish the given time frame in performing the test.
Cinnamaldehyde
Formaldehyde
Acetaldehyde
Benzaldehyde
The disappearance of the red-orange color of chromic acid and the formation of a
blue-green color of the Cr (III) ion indicates a positive test.
The negative result observed by the researchers in the chromic acid test for
Formaldehyde, acetaldehyde, and benzaldehyde might be caused by the impurity of the
reagent or failure to accomplish the given time frame in performing the test.
Cinnamaldehyde Mixture of
potassium
permanganate,
sulfuric acid and
acetaldehyde
Mixture of Mixture of
potassium potassium
permanganate, permanganate,
sulfuric acid and sulfuric acid and
formaldehyde benzaldehyde
The table above shows the actual documentation of what happened after mixing
potassium permanganate, sulfuric acid and formaldehyde, acetaldehyde or benzaldehyde,
made to compare with the isolated cinnamaldehyde.
According to ChemLibreTextsOrg, Potassium permanganate, KMnO4, is a powerful
oxidizing agent, and has many uses in organic chemistry. Of all the oxidizing agents, potassium
permanganate, KMnO4, is probably the most common, and also the most applicable. KMnO4
can be utilized to oxidize a wide range of organic molecules. The products that are obtained
can vary depending on the conditions, but because KMnO4 is such a strong oxidizing agent, the
final products are often carboxylic acids.
Formaldehyde has been identified as a combustion product from many sources including
fuel in automobile and in cigarette smoke. It is used as raw material in many industries. It is an
odorous, lachrymatory and physiologically active compound’. It is regarded as air polluent and
has been established as a primary irritant and mutagen.
When Potassium Permanganate is added to Formalin, there is effervesence, and
resulted to the formation of black coloured bubbles. Also, this reaction is exothermic. The more
the amount of reactants, the more will be the effervesence and heat produced.
Chemical Reaction Incolved:
HCHO + MnO4 HCOO− + MnO2
Formaldehyde (HCHO) is oxidized by potassium permanganate inbasic solution to give
formate ion (HCOO−).
According to PubChem, Acetaldehyde is a widespread, naturally occurring, colorless
and flammable liquid with a suffocating smell. Acetaldehyde is found in various plants, ripe
fruits, vegetables, cigarette smoke, gasoline and diesel exhaust. This substance is widely used
in the manufacture of acetic acid, perfumes, dyes and drugs, as a flavoring agent and as an
intermediate in the metabolism of alcohol.
Aldehydes RCHO are readily oxidized to carboxylic acids.
Chemical reaction involved:
Unless great efforts are taken to maintain a neutral pH, KMnO4 oxidations tend to occur
under basic conditions. In fact, the most effective conditions for aldehyde oxidation by
KMnO4 involves t-butanol as solvent with a NaH2PO4 buffer.
According to PubChem, Benzaldehyde is an aromatic aldehyde bearing a single formyl
group with an almond odor. Benzaldehyde can be derived from natural sources and is widely
used by the chemical industry in the preparation of various aniline dyes, perfumes, flavorings,
and pharmaceuticals.
When Potassium Permanganate is added with benzaldehyde, production of a totally
mixed dark brown solution was produced.
Chemical reaction involved:
C7H6O + KMnO4 C7H6O2 (production of benzoic acid)
Benzaldehyde reacts with potassium permanganate to generate benzoic acid (oxidation).
Cinnamaldehyde milk test, did not produce any colored layer. This indicates that
the milk sample does not contain or is negative for cinnamaldehyde. The researchers
were not able to find any chemical reaction and balanced chemical equation to further
explain the reaction that occurred.
C.5 Polymerization Reaction
Cinnamaldehyde Pale yellow solution
Figure 13. aldol reaction of aldehyde (Chapter 18: Enols and Enolates)
Enolate anions can add to carbonyl groups since they are nucleophiles. When
acetaldehyde is treated with dilute base, it condenses with itself to give Aldol. Upon heating, the
Aldol eliminates a molecule of water , giving the unsaturated aldehyde.
Formaldehyde, on the other hand, did not yield a change or a reaction this id due to the
absence of an alpha carbon, and as stated by Toppr, An alpha carbon is the first carbon that is
joined to the functional group. In the case of aldehydes and ketones, a functional group is a
carbonyl group. The functional group is responsible for the formation of alpha hydrogen. The
hydrogen present on the alpha-carbon is the alpha-hydrogen and it is slightly acidic in nature due
to the carbonyl group and its resonance stabilization mechanism. Thus, alpha-hydrogen and its
acidic nature are responsible for several different reactions, which we will study in this topic.
Hence, no reaction involved in aldol condensation without the alpha carbon.
C.6 Addition Reaction
Cinnamaldehyde Clear solution
The reagent used for the addition reaction of aldehyde is a Saturated solution of sodium
hydrogen sulphide, used to be known as sodium bisulphite. The Addition of sodium hydrogen
sulfite, which proceeds readily with good conversion in aqueous solution with most aldehydes,
methyl ketones, and unhindered cyclic ketones will form to a carbon-sulfur bond. On the other
hand, ketone do not react with sodium bisulphite due to steric hindrance. No catalyst is required
because sulfite is an efficient nucleophilic agent.
CONCLUSION
The experiment allowed the analysts to specify the chemical and physical
properties of aldehydes. Starting from the isolation of cinnamaldehyde from cinnamon, the
analysts were able to confirm that although the compound because it decomposes before it
reached its boiling point (248℃), the vapor pressure attained pressure attained, being equal
to the applied pressure to boil, is the sum of the water vapor pressure and the
cinnamaldehyde pressure. So some compounds comes over in the distillate with water. This
all takes place near 100 ℃ , so the compound is not destroyed. The addition of
dichloromethane serves as a good solvent, allowing the cinnamaldehyde move into the
same layer. The solubility test have also showed that it also depends on the polarity of the
two substances and at the same time to its reaction to the substance helping it attain its
unique characteristic such that in the case of formaldehyde. Furthermore, Tollen’s test have
also proven that it is, indeed, positive with aldehydes since it resulted to positive results of
the different aldehyde containing compounds. The chronic test also showed the oxidation of
aldehydes then reduced the chromic acid to give a color change for the solution. However,
the actual experiment yielded negative results due to possible contamination of reagents
used and since the solution waited for several hours since the isolation of cinnamaldehyde
needed took time. Furthermore, the difference between ketone and aldehydes was further
distinguished since aldehydes contain hydrogen atoms making it more oxidizable than
ketones. Since ketones do not have hydrogen atoms, it appears to be very resistant to
oxidation. However, strong oxidizing agents such as potassium manganate and potassium
permanganate can only oxidize ketones (ChemiLibreTexts). The analysts have also found
out that when milk containing trace of formaldehyde is mixed with an equal volume of water
and and four volumes of concentrated sulfuric acid the solution will soon acquire a violet
color, thus, would indicate the presence of formaldehyde. They have also found out that
certain aldehydes will polymerize in certain pressure 12,000 atm to materials having acetal
structures (Conant, n.d). Lastly, aldehydes will react with amines to form imines.
The experiment, indeed, proved that the comprehensive understanding of these specific
functional group will give an edge to the analysts in their future occupations either as
pharmacists or being in the field of manufacturing. It was found out that the compounds
used such as Formaldehyde is used in biological specimen and preservations. Also, when
reacted with phenol, formaldehyde forms Bakelite, which is used in plastics coatings and
adhesives. Benzaldehyde also shows its use in assays of perfumes, cosmetic products, and
dyes. It is added to food to give almond flavor and also used as bee repellant. Thus, assays
of more insect repellants may arise from knowing the different characteristics of aldehydes.
The analysts conclude that each of the functional group play a significant and unique roles
in many industries. This just proves that the continuation of studies and researches of
budding and veteran inventors and scientists may lead to a better result of products for the
benefit of many people.
REFERENCES
Farmer, Reusch, et.al (May 2019) Nomenclature of Aldehydes and Ketones.
ChemiLibreTexts. Retrieved from:
https://chem.libretexts.org/kbBookshelves/Organic_Cemistry/Supplemental_Modules_(O
rganic_Chemistry)/Aldehydes_and_Ketones/Nomenclature_of_Aldehydes_and_Ketones
March & Brown (n.d) Aldehyde. Britannica.com. Retrieved from:
https://www.britannica.com/science/aldehyde
Science Direct (n.d) Cinnamaldehyde.Retrived from:
https://www.sciencedirect.com/topics/chemistry/cinnamaldehyde
Molecula Level Answers (n.d) The Real Reason why formaldehyde is Toxic—and how to
avoid it. Retrieved from:
https://drholly.typepad.com/question_and_answer_forum/2011/06/th.html
Vissamsetty, Sravya (July 2016) Chemistry is fun. Retrieved from:
https://www.quora.com/Why-is-benzaldehyde-less-soluble-than-acetone-in-water
Gunawardena, Gamini (April 2019) Tollen’s Test. ChemLibreTexts. Retrived from:
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modul
es_(Organic_Chemistry)/Aldehydes_and_Ketones/Reactivity_of_Aldehydes_and_Ket
ones/Tollens%E2%80%99_Test
ByJus’s.com (n.d) Aldehydes and Ketones. Retrieved from:
https://byjus.com/chemistry/aldehydes-ketones/
Judge, M. (2018, March 13) Differences Between Petroleum and Diethyl Ether.
Retrieved from: https://sciencing.com/differences-petroleum-ether-diethyl-ether-
8791792.html
Brown, W. (2011) Benzaldehyde-Chemical Compound. Retrieved from:
https://www.britannica.com/science/science/benzaldehyde
Acetaldehyde (n.d.) Retrieved from:
https://pubchem.ncbi.nlm.nih.gov/compound/acetaldehyde#section=Solubility
Formaldehyde (n.d.) Retrieved from:
https://pubchem.ncbi.nlm.nih.gov/compoun/formaldehyde#section=Solubility
Gale, T. (2006) Chemical Compounds-Cinnamaldehyde. Retrieved from:
https://www.encyclopedia.com/science/academic-and-educational-
journals/cinnamaldehyde
Like Dissolves Like and Molecule Ion Attractions (n.d.) Retrieved from:
https://www.kentchemistry.com/links/bonding/LikeDissolveslike.htm
Bajpal, P. (2017, August 29) Chemistry for CBSE Board. New Delhi:Disha Publications.
Retrieved from:
https://books.google.com.ph/book?id=1uMyDwAAQBAJ&printsec=frontcover&source=gb
s_ge_summary_rcad=0#v=onepage&q&f=false
Embibe. (2019) Polymerisation- Aldehydes and Ketones. Retrived from
https://www.embibe.com/study/polymerisation--aldehydes-and-ketones-concept
Organic Chemistry Portal. (n.d) reaction-name reaction. Retrived from
https://www.organic-chemistry.org/namedreactions/aldol-addition.shtm
Hunt, I. (n.d) Chapter 18: Enols and Enolate. Department of Chemistry,
University of Calgary. Retrieved from
http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch18/ch18-3-4.html
Bicpuc (2016) Aldol Condensation Reaction. Retrieved from
https://medium.com/@bicspuc/aldol-reaction-is-an-important-organic-reaction-of-
aldehydes-and-ketones-c2270617dbbb
Chemistry libretext (2016) 16.4: Typical Carbonyl-Addition Reactions. Retrieved
from
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Book%3A_Basic_Pri
nciples_of_Organic_Chemistry_(Roberts_and_Caserio)/16%3A_Carbonyl_Comp
ounds_I%3A_Aldehydes_and_Ketones._Addition_Reactions_of_the_Carbonyl_
Group/16.4%3A_Typical_Carbonyl-Addition_Reactions
Organicmystery (2018) Nucleophilic Addition Reactions in Aldehydes and
Ketones. Retrieved from
http://www.organicmystery.com/CarbonylGroup/NucleophilicAdditionAldehydesK
etones.php