Experiment 18 Report
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Experiment 18: Qualitative Analysis of Select Functional Group in Organic Compounds
Valentina Espinosa Canon
Laboratory Partners: Dagmawit Duresa
Professor Memari
October 19th, 2023
Abstract
This laboratory experiment aimed to identify and characterize unknown compounds by
employing traditional chemical property tests. The primary objectives were to assess the
compounds' purity, determine their primary functional groups, and utilize solubility and
classification tests to narrow down their identities. Solubility tests in water, HCl, NaOH,
NaHCO3, and concentrated H2SO4 were conducted to evaluate the compounds' chemical nature,
followed by classification tests. Due to challenges in the practical laboratory setting, results were
obtained from instructional videos. Based on these results, six unknown compounds were
tentatively identified. Unknown 1 identified as an alkene, unknown 2 identified as an amine,
unknown 3 as carboxylic acid, unknown 4 as an alcohol, Unknown 5 as a ketone or aldehyde,
and unknown 6 as a ketone or aldehyde. These findings serve as a valuable foundation for further
confirmation of functional group identities. They emphasize the importance of maintaining
proper laboratory techniques to minimize errors and ensure accurate chemical property test
results.
2 Espinosa
Introduction
In this experiment, the main objective is to identify and characterize pure substances
using traditional chemical property tests. Before advanced spectrometric techniques, these tests
were vital in chemical property determination. The initial step involves confirming the purity of
the compound by assessing its boiling or melting point, with a narrow range indicating purity.
After purity verification, the experiment focuses on identifying the compound's primary
functional group. This could be alcohol, ketone, aldehyde, amine, carboxylic acid, or alkene.
This identification process involves solubility tests and functional group classification tests, often
accompanied by IR spectroscopy.
Solubility tests play a critical role in functional group determination. Compounds are first
tested for solubility in water, and the results reveal information about their polar nature.
Subsequent tests involve examining solubility in various solutions, including HCl, NaOH, and
NaHCO3, to narrow down the potential functional groups present. Strong and weak acids react
differently in these solutions, aiding in the identification process. This experiment is a
fundamental approach to characterizing chemical compounds based on their chemical properties
and functional group characteristics.
In the experiment, the solubility tests play a crucial role in guiding the selection of
subsequent classification tests or narrowing down the options. Choosing the right classification
tests is key because conducting all tests might be time-consuming and unproductive. Solubility
test results help in this selection process, as different functional groups display distinct solubility
behavior.
2
3 Espinosa
Moreover, maintaining clean and dry glassware and equipment is essential to prevent
false positive or false negative results. It's critical to note that even a negative result in a
classification test can provide valuable information. Different reagents and conditions yield
specific outcomes for substances with particular functional groups. This enables the distinction
between different functional groups and the identification of specific functional groups in tested
compounds.
In this experiment, various classification tests are discussed to identify specific functional
groups in given compounds. These tests include:
1.
2,4-Dinitrophenylhydrazine Test: This test detects ketones and aldehydes by producing a
distinct colored solid derivative.
2.
Alcoholic Silver Nitrate Test: This test distinguishes alkyl bromides, alkyl iodides, and
carboxylic acids based on the formation of specific solid products.
3.
Bromine in Carbon Tetrachloride Test: Used to identify alkenes by observing the
disappearance of bromine's characteristic color upon reaction.
4.
Ceric Ammonium Nitrate Test: This detects alcohols, with a by a color change in the ceric
ammonium nitrate solution.
5.
Ferric Chloride Test: Used for identifying phenols, which produce distinct colors in ferric
chloride solution.
3
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4 Espinosa
6.
Solubility Tests: These tests involve determining the solubility of compounds in HCl and
NaOH to identify amines and carboxylic acids. Solubility depends on various factors,
including the molecule's size and structure.
7.
Solubility in Concentrated H2SO4: This test identifies unsaturated hydrocarbons, high
molecular weight alcohols, aldehydes, or ketones. It is performed on compounds found
insoluble in water, HCl, and NaOH.
Each test provides information about the presence of specific functional groups in the
compounds, helping to narrow down their identities. It's essential to use these tests selectively
and sequentially to obtain meaningful results.
Materials and Method.
Six different Unknowns.
Water.
HCl.
NaOH.
H
2
SO
4.
NaHCO
3
.
2,4-dinitrophenylhydrazine.
Bromine in Carbon Tetrachloride.
Ceric Ammonium Nitrate.
Test tubes.
Droppers.
Part A: Determine the Purity of a Compound
Measure the boiling or melting point of one of the given compounds.
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5 Espinosa
Verify with the instructor that the obtained boiling/melting point falls within an
acceptable range.
Part B: Test for Solubility
Test the solubility of each compound in water, 5% HCl, 10% NaOH, and 10% NaHCO3.
If a compound dissolves in a solution, determine its pH.
For compounds insoluble in the above solutions, perform a solubility test in concentrated
H2SO4.
Classification Tests
Based on the solubility results, perform classification tests for potential functional groups
like alkenes, alcohols, aldehydes, and ketones.
If the compound remains insoluble in concentrated H2SO4, it could indicate the presence
of alkanes, alkyl halides, or aromatic compounds.
Perform further classification tests as necessary and consider IR spectra if available.
2,4-Dinitrophenylhydrazones for Aldehydes and Ketones:
Dissolve the sample (0.10 g solid or 4 drops of liquid) that did not dissolve in water, HCl,
or NaOH but dissolved in H2SO4 in ethanol.
Add 2,4-dinitrophenylhydrazine/sulfuric acid reagent.
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6 Espinosa
Allow crystallization at room temperature, heat if necessary.
The absence of crystals might indicate the absence of an aldehyde or ketone functional
group.
Tollens' Test for Aldehydes:
Mix 2 mL of 5% aqueous silver nitrate with 1 drop of 10% sodium hydroxide.
Gradually add 2 M aqueous ammonia until dark Ag2O precipitate dissolves.
Add 0.05 g of the compound and let it stand for 5-10 minutes.
Observe for a silver mirror; its presence indicates an aldehyde.
Bromine in Carbon Tetrachloride:
Dissolve the sample (4 drops of liquid or 0.1g of solid) in ethanol or carbon tetrachloride.
Slowly add a 5% solution of bromine in carbon tetrachloride drop by drop.
Note observations, including the number of drops required for the bromine color to
persist.
Ceric Ammonium Nitrate Test for Alcohols:
Add 1 mL of the compound to a dry test tube.
Add ceric ammonium nitrate reagent and shake the solution.
6
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7 Espinosa
Observe the solution for immediate red or red-brown color, indicating a positive test for
alcohols.
These tests help identify specific functional groups within the compounds and are conducted
sequentially to narrow down the possibilities. Proper waste disposal and cleaning procedures are
important after conducting the tests.
Data:
Table 1: Raw Data: Solubility in water
Unknown
Water
Observations
Unknown 1
No soluble
Two layers formed, with a slightly oily layer on top containing
visible oil droplets.
Unknown 2
No soluble
A cloudy solution was observed.
Unknown 3
No soluble
The solid did not dissolve.
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8 Espinosa
Unknown 4
No soluble
solution remained cloudy with oil droplets moving up and
down.
Unknown 5
No soluble
Solid did not dissolve.
Unknown 6
No soluble
Solution appeared oily.
Table 2: Raw Data: Solubility in HCl
Unknown
HCl
Observations
Unknown 1
No soluble
Two layers formed.
Unknown 2
Soluble
Solution became transparent and clear.
Unknown 3
No soluble
Solid did not dissolve.
Unknown 4
No soluble
Two layers formed.
Unknown 5
No soluble
Solid did not dissolve.
Unknown 6
No soluble
Two layers formed.
Table 3: Raw Data: Solubility in NaOH
Unknown
NaOH
Observations
Unknown 1
No soluble
Two layers formed.
Unknown 3
Soluble
Solid dissolved.
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9 Espinosa
Unknown 4
No soluble
Two layers formed, with a slightly oily layer.
Unknown 5
No soluble
Solid did not dissolve.
Unknown 6
No soluble
Two layers formed with some white precipitate.
Table 4: Raw Data: Solubility in H
2
SO
4
Unknown
H
2
SO
4
Observations
Unknown 1
Soluble
Color changed to a light yellow.
Unknown 4
Soluble
Color changed to a light yellow.
Unknown 5
Soluble
Solid dissolved, and the color became very pale
yellow.
Unknown 6
Soluble
Color changed to a light orange.
Table 5: Raw Data: Classification Tests: 2,4-Dinitrophenylhydrazones for Aldehydes and
Ketones
Unknown
C
6
H
6
N
4
O
4
Observations
Unknown
1
No reaction
Color did not change, and no crystals were
observed.
Unknown
No reaction
Color did not change, and no crystals were
9
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4
observed.
Unknown
5
Reaction occurred
Precipitate in the form of crystals was observed.
Unknown
6
Reaction occurred
Precipitate in the form of crystals was observed.
Table 6: Raw Data: Classification Tests: Bromine in Carbon Tetrachloride
Unknown
Bromine in Carbon
Tetrachloride
Observations
Unknown
1
Reaction occurred
The brown color of bromine disappeared.
Unknown
4
No reaction
Brown color of bromine did not disappear.
Table 7: Raw Data: Classification Tests: Ceric Ammonium Nitrate Test
Unknown
Bromine in Carbon
Tetrachloride
Observations
Unknown
4
Reaction occurred
Solution turned red.
Table 8: Raw Data: Classification Tests: Sodium Bicarbonate.
Unknown
NaHCO
3
Observations
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11 Espinosa
Unknown
3
Reaction occurred
Bubbles were observed, and then the solution
completely dissolved.
Table 9: Raw Data: Identification of functional groups.
Unknown
Functional Group
Unknown 1
Alkene.
Unknown 2
Amine.
Unknown 3
Carboxylic acid.
Unknown 4
Alcohol.
Unknown 5
Ketone or Aldehyde.
Unknown 6
Ketone or Aldehyde.
Discussion:
The experiment aimed to identify the primary functional groups within the compounds.
This identification process involved solubility tests, and functional group classification tests. The
solubility tests were crucial in narrowing down the potential functional groups within the
compounds. The solubility behavior of compounds in different solvents provided valuable
insights into their chemical nature.
11
12 Espinosa
In the water solubility test, it was observed that Unknowns 1, 2, 3, 4, 5, and 6 did not
dissolve, suggesting that they were not water-soluble. Unknown 1 and Unknown 5 displayed two
layers with an oily appearance, indicating limited solubility in water. The results hinted at the
possibility that these compounds were non-polar.
In the HCl solubility test, Unknowns 2 was soluble, while the others (Unknowns 1, 3, 4,
5, and 6) did not dissolve. The solubility of Unknown 2 in HCl indicated that it had basic
properties, as basic compounds tend to be soluble in acidic solutions.
In the NaOH solubility test, Unknowns 3 displayed solubility, while the rest (Unknowns
1, 4, 5, and 6) did not dissolve. This solubility of Unknown 3 in NaOH suggested it contained an
acidic functional group, as acidic compounds tend to be soluble in basic solutions. The lack of
solubility in NaOH for the other compounds indicated their non-acidic nature. In the NaHCO3
solubility test, Unknown 3 exhibited a reaction by forming bubbles, suggesting the presence of a
carboxylic acid functional group. In the concentrated H
2
SO
4
solubility test, Unknowns 1, 4, 5,
and 6 dissolved and exhibited color changes, indicating the presence of specific functional
groups.
Based on the results of the solubility tests, further classification tests were performed to
identify specific functional groups within the compounds. In the 2,4-Dinitrophenylhydrazone
Test Unknowns 5 and 6 exhibited a reaction by forming crystals, suggesting the presence of
aldehyde or ketone functional groups. The absence of crystals for Unknowns 1 and 4 indicated
the absence of aldehyde or ketone groups.
12
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For Bromine in Carbon Tetrachloride Test Unknown 1 displayed a reaction by the
disappearance of the brown color of bromine, indicating the presence of an alkene. However,
Unknown 4 did not show a reaction, suggesting the absence of an alkene. To confirm Unknown 4
identity a Ceric Ammonium Nitrate Test was performed.
Unknown 4 displayed a reaction by
turning red, indicating the presence of an alcohol.
Based on the results of the classification tests and solubility tests, we can tentatively
identify the functional groups in each of the unknown compounds. Unknown 1 is Alkene,
Unknown 2 is an Amine, Unknown 3 is Carboxylic acid, Unknown 4 an Alcohol, Unknown 5
Ketone or Aldehyde and Unknown 6 Ketone or Aldehyde.
Conclusion.
The primary objective of this laboratory experiment was to identify and characterize
unknown compounds functional group through the application of traditional chemical property
tests. These time-honored tests played a crucial role in chemical analysis before the advent of
advanced spectrometric techniques.
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14 Espinosa
This identification process involved solubility tests and functional group classification
tests. The solubility tests played a pivotal role in narrowing down the potential functional groups
present in the compounds, offering insights into their chemical nature.
It is important to note that, due to certain complications in the practical laboratory setting,
the results discussed here were obtained from the professor's instructional videos. These
complications arose from challenges related to identification and observation, which could
impact the results accuracy.
The solubility tests in water, 5% HCl, 10% NaOH, and 10% NaHCO3 served as a
foundation for understanding the chemical properties of the compounds. Each of these solutions
was chosen to assess the solubility of the compounds under different pH conditions and observe
their interactions in acidic and basic environments.
In the water solubility test, the compounds (Unknowns 1, 2, 3, 4, 5, and 6) were observed
not to dissolve, indicating limited or no water solubility. In the case of Unknowns 1 and 5, two
layers with an oily appearance were observed, suggesting reduced solubility in water. These
results suggested the possibility of these compounds being non-polar or hydrophobic in nature.
In the HCl solubility test, Unknown 2 was soluble, while the other compounds (Unknown
1, 3, 4, 5, and 6) did not dissolve. The solubility of Unknown 2 in HCl suggested the presence of
basic properties, as basic compounds tend to dissolve in acidic solutions. The lack of solubility of
the other compounds in HCl provided further information about their non-basic nature.
In the NaOH solubility test, Unknown 3 was observed to be soluble. This solubility of
Unknown 3 in NaOH indicated the presence of an acidic functional group, as acidic compounds
14
15 Espinosa
tend to be soluble in basic solutions. The non-solubility of NaOH compounds indicated their
non-acidic nature. In the NaHCO3 solubility test, Unknown 3 displayed a reaction by producing
bubbles, suggesting the presence of a carboxylic acid functional group.
In the concentrated H2SO4 solubility test, unknowns 1, 4, 5, and 6 dissolved and
exhibited color changes, indicating the presence of specific functional groups. The light-yellow
color change in Unknown 1, 4, 5 suggested the presence of an unsaturated hydrocarbon or a high
molecular weight alcohol, aldehyde, or ketone. The light orange color change in Unknown 6
indicated the presence of a high molecular aldehyde or ketone.
Based on the outcomes of the solubility tests, further classification tests were conducted
to identify specific functional groups within the compounds. In the first test, 2,4-
Dinitrophenylhydrazone was used. As a result of the formation of crystals, unknowns 5 and 6
showed reactions that suggest the presence of aldehydes or ketones as functional groups. The
absence of crystals for unknowns 1 and 4 indicated the absence of aldehyde or ketones groups.
By using a bromine-in-carbon tetrachloride test, Unknown 1's functional group identity
was confirmed since it displayed a reaction resulting in the disappearance of bromine's brown
color, indicating the presence of an alkene. However, Unknown 4 did not exhibit a reaction,
suggesting the absence of an alkene. Then a Ceric Ammonium Nitrate Test was performed on
Unknown 4. It displayed a reaction by turning red, indicating the presence of alcohol.
Based on the results of the classification tests and solubility tests obtained from the
professor's instructional videos, we can tentatively identify the functional groups in each of the
unknown compounds. Unknown 1 is Alkene, Unknown 2 is an Amine, Unknown 3 is a
15
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Carboxylic acid, Unknown 4 an Alcohol, Unknown 5 is Ketone or Aldehyde, and Unknown 6 is
a Ketone or Aldehyde.
In conclusion, despite the challenges faced in the practical laboratory, the combination of
solubility tests and classification tests, along with the guidance from the professor's instructional
videos, provided valuable information for identifying potential functional groups within the
unknown compounds. Further confirmatory tests and the use of IR spectroscopy, if available,
could help refine the identifications and provide more conclusive results. Overall, the laboratory
experience was invaluable in providing us with a deeper understanding of the functional groups
and their properties. The laboratory also gave them an opportunity to practice their laboratory
skills.
Bibliography:
Memari, Behnoush. CHM 2211L - Broward College-Central. Available from: VitalSource
Bookshelf, (5th Edition). Macmillan Higher Education, 2023.
16
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- 1. Benzoic acid is a stronger acid than benzyl alcohol by more than ten orders of magnitude, despite both containing a hydroxyl group. Why? Draw structures to support your answer.arrow_forwardSalicylic acid, HOC6H4CO2H, and its derivatives have been used as pain relievers for a long time. Salicylic acid occurs in small amounts in the leaves, bark, and roots of some vegetation (most notably historically in the bark of the willow tree). Extracts of these plants have been used as medications for centuries. The acid was first isolated in the laboratory in 1838. (a) Both functional groups of salicylic acid ionize in water, with Ka = 1.0 ×× 10−3 for the—CO2H group and 4.2 ×× 10−13 for the −OH group. What is the pH of a saturated solution of the acid (solubility = 1.8 g/L). (b) Aspirin was discovered as a result of efforts to produce a derivative of salicylic acid that would not be irritating to the stomach lining. Aspirin is acetylsalicylic acid, CH3CO2C6H4CO2H. The −CO2H functional group is still present, but its acidity is reduced, Ka = 3.0 ×× 10−4. What is the pH of a solution of aspirin with the same concentration as a saturated solution of salicylic acid (See Part a).arrow_forwardSee image belowarrow_forward
- In the following acid - base reactions, a) Draw Lewis structures of the reactants and the products. b) Determine which species are acting as electrophiles (acids) and which are acting as nucleophiles (bases). c) Use the curved - arrow formalism to show the movement of electron pairs in these reactions and the imaginary movement in the resonance hybrids of the products. d) Indicate which reactions are best termed Brønsted-Lowry acid - base reactions i. CH3CHO + HCI-- > CH3CH2O + + Cl- ii. CH3CHO + OH- - - > CH3CO-(OH) Harrow_forwardDraw the Lewis structures for chloroacetic acid and for acetic acid. Use structural arguments to explain why acetic acid is a weaker acid then chloroacetic acid. Be sure to refer to the stability of the ion that would be formed after dissociation of the acid.arrow_forwardAlkaloids are basic nitrogen-containing compounds of plant origin, many of which are physiologically active when administered to humans. Ingestion of coniine, isolated from water hemlock, can cause weakness, labored respiration, paralysis, and eventually death. Coniine is the toxic substance in the “poison hemlock” used in the death of Socrates. In small doses, nicotine is an addictive stimulant. In larger doses, it causes depression, nausea, and vomiting. In still larger doses, it is a deadly poison. Solutions of nicotine in water are used as insecticides. Cocaine is a central nervous system stimulant obtained from the leaves of the coca plant.Classify each amino group in these alkaloids according to type (primary, secondary, tertiary, aliphatic, aromatic, heterocyclic).arrow_forward
- Can you please answer this question by detailsarrow_forwardDr. Frank's Magical Cure-all Cough Syrup contains three ingredients, shown below. You seek to isolate these three ingredients to further quantify and analyze them, something that can be achieved via liquid-liquid extraction. Propose a flow chart demonstrating how you would separate each of the components into a distinct organic layer. This flowchart should represent all of the chemicals required for the separation, and depict accurate representations of the chemical species throughout the process. H H. НОarrow_forwardIdentify the functional groups in the following molecules. (Use names from the table below. List each class of functional group only once. If there are fewer than 3 functional groups, leave an appropriate number of answer boxes empty.) HO CHS a) b) OH amine Carboxylic Acid Give detailed Solution with explanation needed, don't give Handwritten answer arene NH₂ phenylalaninearrow_forward
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