Differentiating the Organic Compounds via Comparative Investigation of their Properties

Isabella Guce, Janisa Gutierrez, Krystel Leobrera, Christiane Lim, Hedrick Lim Group 5 2B Pharmacy Organic Chemistry Laboratory

ABSTRACT
The group differentiated the different organic compounds namely Cyclohexene, DCM, Ethanol, Phenol, Benzoic Acid, Ethyl Acetate, and Ethylamine via Comparative Investigation of their properties. The investigation included the test for the organic compounds intrinsic physical properties, behaviour in ignition, reaction with litmus paper and their infrared spectra. The physical state of all the organic compounds except benzoic acid is liquid while the latter is solid. All organic compounds have distinct odors and are colorless except red colored phenol and white Benzoic Acid. Solubility and miscibility were also tested in the following reagents: in water in which every compound except Benzoic Acid, Phenol and Ethylamine were immiscible or insoluble; in 5% NaOH in which Cyclohexane, DCM, and Ethyl Acetate were immiscible or insoluble; and in 5% HCL solution wherein only Ethylamine and Ethanol were miscible or soluble. Based on the compounds reaction in the litmus paper, Ethanol was acidic and Ethylamine and Benzoic Acid were basic. Ignition test was conducted with 3 to 5 drops of the sample wherein DCM, Phenol, Benzoic Acid were inflammable. Lastly, the infrared spectrum was use to classify organic compounds according to their functional groups.

INTRODUCTION
The objective of the experiment is to differentiate organic compounds with each other which can be done due to the difference in their structure and composition that brought about certain intrinsic physical properties, different behavior towards flame and difference in their infrared spectra. Organic compounds are classified into hydrocarbons and hydrocarbon derivatives. Hydrocarbon is the simplest organic compound containing only hydrogen and carbon. [1] Hydrocarbon can be further classified as unsaturated and saturated hydrocarbons. Unsaturated hydrocarbons contain double bonded and triple bonded carbon bonds while saturated hydrocarbons contain single bonded carbon. These two classes have similar physical properties but different chemical properties. [2] The strength of the interactive forces between these molecules also brought about difference in their physical state. The combination of carbon and hydrogen is always non-polar. This makes hydrocarbons insoluble in water. Furthermore, the dissolution of organic compound in certain solvents differs due to their varying polarities. On the other hand, hydrocarbon derivatives are compounds made up of carbons and one or more functional groups. [1] A functional group is a special arrangement of atoms that is mainly responsible for the chemical behaviour and some intrinsic physical properties of a molecule. [3] The ignition test is based on the principle of flammability. Flammability is the measure of the extent to which a substance will support combustion. [4] Compounds that contain high carbon content produce yellow, sooty flame. Infrared (IR) spectrometry gives additional information about a compounds structure. It identifies the type of principal bond present in the sample compound, gives its wave number range and identifies the functional group present in the compound. [5]

EXPERIMENTAL
A. Materials Cyclohexane, DCM, Ethanol, Phenol, Benzoic acid, Ethyl acetate, Ethylamine

B. Procedure
In order to conduct the experiment, the following procedures were accomplished: 1. Physical State, Color and Odor During this process, the physical state of the samples at room temperature, color and odor of each compound was noted and observed by the group. 2. Solubility Properties During this process, the sample which was 4 drops if liquid and .1 g if solid was introduced to a solvent reagent. The solvent was added drop wise and counted until it reached a total of 3mL. Any change in the sample was noted. 3. Reaction with Litmus Paper
During this process, drops of the sample soluble in water were reacted with red and blue litmus papers. Color changes in both litmus papers were noted.

H20, 5% NaOH solution and 5% HCL solution indicates whether the sample is soluble or insoluble and if the sample is miscible and immiscible. The difference in their solubility was brought about by their difference in polarities and interactive forces. Based on the results, all organic compounds with an exception of phenol, Benzoic Acid and ethylamine were insoluble or immiscible in H20 because they were non-polar. Polar compound such as phenol and ethylamine was soluble in water but phenol was less soluble due to the presence of the nonpolar benzene ring in its structure. Benzoic was slightly miscible in water because of the polar carboxylic acid in its structure. The water soluble compounds were basic with an exception of ethanol which was acidic due to deprotonization. In 5% NaOH solution, compound such as
Cyclohexane, DCM and Ethyl acetate were insoluble. Cyclohexane was insoluble because its an inert compound and insoluble in everything. On the other hand, DCM as a cyclohexene was immiscible in weak acids, and Ethyl Acetate was immiscible due to its absence of strong hydrogen bonding. Ethylamine and Ethanol were miscible in 5% HCl solution because its a strong acid. Most

4.Ignition Test During this process, 3-5 drops of the liquid sample and a pinch amount of solid were placed in an evaporating dish and was lighted using a match. Any flame produced and observed was noted. The color of the flame and the burning time was also noted. 5. Infrared (IR) Analysis During this process, appendix notes was used as a reference to identify the type of principal bond present in the sample compound, IR spectra that may be observed and its wave number range was given.

alcohols and alkanes which contain only saturated carbons were flammable during the ignition test due to their ease of reaction with oxygen. Unsaturated carbon-carbon bond such as DCM, Phenol,
Benzoic Acid were inflammable during ignition test. Ethanol had a blue flame due to

complete combustion and the carbon was completely oxidized. 2 C10H22 + 31 O2 -> 20 CO2 + 22 H2O Orange and yellow flame of ethyl acetate, ethylamine, and cyclohexane indicated incomplete combustion wherein the carbon was not completely oxidized. 2C2H2 + 5O2 = 4CO2 + 2H2O + heat. For IR spectrometry, the position of the band depends upon a number of characteristics of a bond. The higher the bond order, the higher the wave number for the stretching vibration for a bond.

RESULTS AND DISCUSSION

Most of the hydrocarbons were colorless with an exception of Phenol that became red upon oxidation and white crystals of benzoic acid. All organic compounds have distinct odors that were presented in the table. Solubility properties of organic compounds using

Overall, the experiment had differentiated the organic compounds based on certain intrinsic physical and chemical properties, on the behavior towards ignition and on the infrared spectra of their functional groups. The table below shows the summary of results.

Test Compounds Physical State Color Odor Solubility in H20 5% NaOH 5% HCl Reaction with litmus paper
Ignition test Observed principal IR peaks(cm-1)

Benzoic Acid
Solid

Phenol Liquid

white sweet

red Burnt-like odor

Table 1.1 Results

Test Compound Physical State Color Odor
Cyclohexane DCM Ethanol Pheno l
Liquid clear orange

insoluble soluble insoluble

Slightly miscible miscible immiscible

Liquid Colorless Rubberlike

Liquid Colorless odorless

Liquid Colorless Alcohol like -

Burntlike odor

Solubility in H2O 5% NaOH

immiscible immiscible

immiscible immiscible

miscible miscible

Slightly misicibl e Misc ible immisci ble

Nonflammable O-H stretch*(broad s) 3300-2500 C=O stretch*(s) 1730-1680 0-H bend(m) 1440-1390 C-O stretch(s) 1320-1210

Nonflammable O-H Stretch(vs) *3100-3000 0-H Bend(m-w) 1420-1340 C-O Stretch(s-m) 1230-1000

5% HCl

immiscible

immiscible

miscible

Reaction with litmus paper Ignition test

acidic

Orange (12 sec.) C-H stretch(s) *3000-2840 C-H bend(sm)* 14751350 C-C stretch(vw) * 1200-800

Nonflammable
C-H stretch(s) *30002840 C-H bend(sm)* 14751350 C-C stretch (vw)* 1200-800

Blue (11 sec.)

O-H Stretch(vs) *31003000 0-H Bend (m-w) 1420-1340 C-O Stretch (sm)12301000

Acidic BlueRed RedRed Nonflamma ble

Observed principal IR peaks(cm-1)

O-H Stretch (vs) *31003000 0-H Bend( m-w) 14201340 C-O Stretch (s-m) 12301000

Test compounds Physical state at RT Color Odor Solubility in: H2O 5% NaOH soln. 5% soln. HCl

Ethyl acetate
Liquid

Ethylamine
Liquid

[5] Infared Spectrum (n.d.). In Encyclopdia Britannica online. Retrieved from http://www.britannica.com/EBchecked/to pic/724633/infared spectrum

colorless Fruity odor

Colorless Urine odor

immiscible imiscible

Miscible miscible

immiscible

miscible

Reaction/
litmus paper

basic

Ignition test

Yellow ; 5 sec

Orange;8 sec

Observed principal IR peaks(cm-1)

C=O stretch*(s) 1740-1710 C-O stretch(s) 1245-1190

N-H stretch*(s) 3500-3300 & 3400-3200 N-H bend*(s) 1640-1560 N-H bend(broad m) 900-650 C-N stretch(s-m) 1330-1030

References
[1] Hydrocarbons, (n.d.). Retrieve from http://chemed.chem.wisc.edu/chempaths/ GenChem-Textbook/Organic-CompoundsHydrocarbons-581.html on Sept 6, 2013. [2] Bayquen, A., Cruz, C., et.al (2009). Labaratoy Manual in Organic Chemistry. Quezon City: C&E Publishing. [3]Hydrocarbon Derivatives (2011). Retrieved from www.mcgrawhill.ca/school/files/2011/08/ Chapter-1-Section-1.3.pdf on Sept 6, 2013 [4] Flammability (n.d.). In Encyclopdia Britannica online. Retrieved from http://www.britannica.com/EBchecked/to pic/724633/flammability