Experiment #7: Classification Tests for Hydrocarbons CAVIDA, C.M.B., *CHOSANTOS, D.B., CHUA, K.B.C., CO, E.K.T, CRISOL, D.B.

2C-MT, Faculty of Pharmacy, UST Abstract In this experiment 5 organic compounds which were Hexane, Heptane, Cyclohexane, Benzene, and Toluene were used. These Organic compounds were observed in terms of its intrinsic physical properties and its chemical properties in terms of structure and behavior. By simple observation we noted its color and odor. Also, a test in concentrated 1 mL H2S04 was conducted to differentiate which compounds were immiscible or not, then observation of any change and/or warming effect was also noted. Ignition test was also conducted to test the flammability of the organic compounds by adding 3-5 drops of the sample in an evaporating dish and lighting it with a match. Baeyer¶s test and Bromine test was also conducted to test the organic compounds for active saturation. In Baeyer¶s test, 5 drops of sample was added to 2 drops of 2% KMn04. The observation of any brown suspension was noted and decolorization of the reagent was immediate if it occurred within 1 minute. While in Bromine test, 5 drops of sample was added to 10 drops of .5% Br2 in CCl4 reagent and if the reagent failed to decolorize within 1 minute exposure to sunlight was done. Then Test for Aromaticity: Nitration was conducted to determine the miscibility of the 5 organic compounds by mixing 5 drops of the sample and 8 drops of nitrating mixture, formation of any yellow oily layer was observed and water bath was also conducted. Lastly test for basic oxidation was done to note if any precipitate was formed when 4 drops of sample was added to 8 drops of 2% KMn04 & 10% NaoH solution. The organic compounds were tested if it is saturated, actively unsaturated, aromatic or an arene. Introduction: Hydrocarbons are the compounds which are composed of Hydrogen and Carbon. Each carbon atoms has four bonds. They can be saturated (single bond), unsaturated (double or triple bond), acyclic (without rings) and cyclic (with rings). Saturated hydrocarbons are known when all the valencies of carbon atoms are fully utilized by single covalent bonds. The parent molecule of saturated hydrocarbon is methane. A number of carbon atoms can be linked together without any limitations. Examples are : Alkanes (methane, ethane, propane etc.) Unsaturated hydrocarbons have one or more double or triple bonds between carbon atoms. Those with double bond are called alkenes. Those with one double bond have the formula CnH2n (assuming non-cyclic structures). Those containing triple bonds are called alkynes, with general formula CnH2n-2.

(Figure 2: Example of an Unsaturated Hydrocarbon) Hexane is a chemical made from crude oil. Pure hexane is a colorless liquid with a slightly disagreeable odor. It evaporates very easily into the air and dissolves only slightly in water. Hexane is highly flammable, and its vapors can be explosive. is a hydrocarbon with the chemical formula C6H14; that is, an alkane with six carbon atoms. In the IUPAC nomenclature, however, hexane is the unbranched isomer (n-hexane); the other four structures are named as methylated derivatives of pentane and butane.

(Figure 1: Example of a saturated Hydrocarbon)

(Figure 3: Ex. Of hexane)

Heptane is a volatile, colorless, highly flammable liquid hydrocarbon, C7H16, obtained in the fractional distillation of petroleum and used as a standard in determining octane ratings, as an anesthetic, and as a solvent. It is also a straight-chain alkane. r.d. 0.684; m.p. ±90.6°C; b.p. 98.4°C. In standardizing octane numbers, heptane is given a value zero.

regular hexagon. The hexagon symbol, commonly used to represent the structural formula for benzene, implies the presence of a carbon atom at each of the six angles and, unless substituents are attached, a hydrogen at each carbon atom. Whereas the three double bonds usually included in the formula are convenient in accounting for the addition reactions of benzene, present evidence is that all the carbon-to-carbon bonds are identical.

(Figure 4: Example of Heptane) Cyclohexane is a colorless liquid cycloalkane, C6H12; r.d. 0.78; m.p. 6.5°C; b.p. 81°C. It occurs in petroleum and is made by passing benzene and hydrogen under pressure over a heated Raney nickel catalyst at 150°C, or by the reduction of cyclohexanone. It is used as a solvent and paint remover and can be oxidized using hot concentrated nitric acid to hexanedioic acid (adipic acid). The cyclohexane ring is not planar and can adopt boat and chair conformations; in formulae it is represented by a single hexagon. It is extremely flammable, colorless, mobile liquid, used in the manufacture of nylon and as a solvent, a paint, and a varnish remover.

(Figure 6: Example of Benzene) Toluene, C7H8, colorless liquid aromatic hydrocarbon that melts at í95°C and boils at 110.8°C. It is insoluble in water but highly soluble in most organic solvents. Toluene is obtained from coal tar and petroleum by distillation. It is used as a solvent and as a starting material for the synthesis of many compounds, including dyes and explosives. When toluene is treated with a mixture of nitric and sulfuric acids (a process known as nitration), trinitrotoluene (TNT) is produced. It is formerly known as toluol, is a clear, waterinsoluble liquid with the typical smell of paint thinners. Chemically it is a mono-substituted benzene derivative, i.e. one in which a single hydrogen atom from the benzene molecule has been replaced by a univalent group, in this case CH3. It is an aromatic hydrocarbon that is widely used as an industrial feedstock and as a solvent.

(Figure 5: Example of Cyclohexane) Benzene: Is a colorless, liquid, inflammable, aromatic hydrocarbon of chemical formula C6H6 which boils at 80.1°C (176.2°F) and freezes at 5.4±5.5°C (41.7±41. The six carbon atoms of benzene, each with a hydrogen atom attached, are arranged symmetrically in a plane, forming a

(Figure 7: Example of Toulene)

Flammability is a test where it checks a number of properties. Almost all organic compounds (compounds containing C and H primarily in combination with O, N, and other non-metals) are readily flammable (Fully halogenated carbon compounds are notable exception). Flammability means that the compound can react exothermically with oxygen. Because of the high heat of reaction, it means a fire will result from the reaction. Most alcohols and alkanes are prime examples. Their high flammability is the result of their ease of reaction with oxygen, and the large amount of heat given out when they react. This heat results from the formation the bonds in CO2 and H2O, which are very stable and have less energy than the bonds of the initial reactants. The excess energy is lost as heat. Hydrocarbon Solubility : The rule to use when determining hydrocarbon solubility is: Like dissolves like. This means that polar compounds (water, alcohols, and carboxylic acids) dissolve other polar compounds. Nonpolar compounds dissolve other nonpolar compounds but tend not to dissolve polar compounds. When you test for solubility you are looking for either a homogeneous solution or a heterogenous solution. Homogeneous solutions have no layers evident indicating the hydrocarbon being tested is soluble. These hydrocarbons are miscible. Heterogenous solutions have layers evident indicating the hydrocarbons are insoluble. These hydrocarbons are immiscible. Miscibility is the property of liquids to mix in all proportions, forming a homogeneous solution. In principle, the term applies also to other phases (solids and gases), but the main focus is usually on the solubility of one liquid in another. Water and ethanol, for example, are miscible since they mix in all proportions. By contrast, substances are said to be immiscible if in some proportion, they do not form a solution. For example, diethyl ether is fairly soluble in water, but these two solvents are not miscible since they are not soluble in all proportions. Like any other solubility phenomenon, miscibility depends on the forces of attraction between the molecules of the different liquids. The rule of thumb "like dissolves like" means that liquids with similar molecular structures, in particular similar polarity, will likely dissolve in each other. (Polarity means the extent to which partial positive and negative charges appear on

a molecule, because of the type and arrangement of its component atoms.) Both water and ethyl alcohol have very polar hydroxyl groups (-OH) on their molecules, and therefore both undergo the strong intermolecular attraction known as "hydrogen bonding." Hexane, on the other hand, is not miscible with water because its molecular structure contains no polar groups of any kind that would be attracted to the water molecules. The Baeyer test for unsaturation is for determining the presence of carbon-carbon double bonded compounds, called alkenes or carbon-carbon trible bonded compounds, called alkyne bonds. The Baeyer test uses dilute Pottasium Permanganate to Oxidize the carboncarbon double or triple bond. It¶s called oxidation because the double bond is replaced by a hydroxy group (an OH group). The carbon¶s charge goes from being +1 to +2, so it loses an electron (and is thus oxidized) Reaction for alkenes

(Figure 8: Reaction of Baeyer¶s Test)

An alkene is replaced with a diol (a compound with 2 hydroxy groups). Evidence for the reaction is there because the purple Pottasium permanganate goes colorless. Alkynes work the same way, but a 4 hydroxy quattrol is produced (with 2 hydroxy groups on each carbon). The reaction is important because it doesn¶t work on alkanes (compounds with carbon carbon single bonds) or aromatic compounds. However, the test has a few drawbacks. Aldehydes (terminal carbonyls ... carbon double bonded to Oxygen) will also be oxidized (to carboxylic acids) and formic acid (ethanoic acid) and its esters are known to give positive tests. The Bromine test is used to determine if the colorless organic compound contains any double C=C bonds (the alkene functional group).

Bromine does not react with an alkane because the alkane contains only single C-C bonds which cannot add the bromine. Alkanes merely dilute the red-brown bromine color to an orange or yellow color in the absence of a strong catalyst. Due to their C=C double bonds which can be broken, alkenes react readily with bromine to produce saturated dibromoalkanes. When an alkene is reacted with bromine, the red-brown color of the bromine is immediately lost due to the reaction of the bromine. Unsaturation and Alkanes and Alkenes: Alkanes are considered saturated because they have only single C-C bonds and cannot add hydrogen. Alkenes are unsaturated because they are capable of adding a hydrogen when the C=C double bond is broken. Aromaticity is a property associated with the extra stability of certain types of p systems. Fundamentally it arises from having the maximum number of electrons in the p bonding molecular orbital¶s. As we will see, it is not restricted to benzene, substituted benzenes, 6-membered rings or just hydrocarbons. The property of aromaticity is generally about a significant extra stability associated with a resonance delocalized structure. This extra stability moderates the reactivity of these systems compared to alkenes and means aromatics can be considered as their own functional group. The presence of aromatic systems can also influence the reactivity of functional groups directly attached to the aromatic system particularly in the benzylic position. Therefore it is important that you are able to recognise the aromatic systems. Basic oxidation was done using potassium permanganate, it is an inorganic chemical compound with the formula KMnO4. It ± + is a salt consisting of K and MnO4 ions. Formerly known as permanganate of potash or Condy's crystals, it is a strong oxidizing agent. It dissolves in water to give intense purple solutions, the evaporation of which gives prismatic purplish-black glistening crystals. NaOH was also used to help determine if the samples used will be forming a precipitate or not. Methodology: A. Physical state, color, and odor

The physical state of the organic compounds hexane, heptanes, cyclohexane, benzene and toluene were physically examined at room temperature. The color was noted with a wafting motion of the hand over the mouth of the test tube. The color should be noted by physical observation. B. Solubility in concentrated H2S04 Add a drop of the sample cautiously to about 1 mL of conc. H2S04 by using dry and calibrated droppers. C. Ignition Test Place 3-5 drops of the liquid sample in a small evaporating dish and light with a match. If the sample is solid, use a pinch amount. D. Test for Active Unsaturation a. Baeyer¶s test : Place 5 drops of the sample in a dry tes tube. Add two drops of 2% KMn04 solution. Shake the test tube vigorously and observe the rate and extent at which the reagent is decolorized. *note the formation of a brown suspension. Compare with water as a negative control. Decolorization of the reagent is immediate if it occurs within 1 minute. b. Bromine test: Place 5 drops of the sample in a dry test tube. Add 10 drops 0.5 Br2 in CCl4 reagent. Shake the test tube vigorously and observe the rate and extent (color change) by which the reagent is decolorized: the bromine color is discharged. Then compare with water as a negative control. If the reganet failed to decolorized within 1 minute, expose the reaction mixture to sunlight. E. Test for Aromaticity: Nitration Place 2 mL of conc. HN03 in an Erlenmeyer flask in an evaporating dish containing water and gradually 2 mL of conc. H2S04. Cool the resulting mixture

to room temperature. This will serve as the nitrating mixture. Place 5 drops of the sample in a dry test tube. Add 8 drops of the nitrating mixture and shake the test tube to ensure complete mixing. Note the formation of yellow oily layer or droplet. Dilute with 20 drops of water. If there no apparent reaction observed within a minute, place the test Results and Discussion:

tube in a water bath for 10 minutes. Dilute with 20 drops of water. F. Basic oxidation To 4 drops of the sample in the test tube, add 8 drops of 2% KMn04 solution and 3 drops of 10% NaOH solution. Warm each test tube in a water bath for 2 minutes and observe color change and the formation of precipitate.

Compounds Studied

Hexane

Heptane Cyclohexane

Benzene

Toluene

Condensed structural formula

A. Physical State at RT Color Odor B. Solubility in Concentarted H2S04 Inference C. Ignition Test Inference D. Baeyer's test Bromine test Inference E. Test for aromaticity: nitration Inference F. Basic Oxidation Inference

Liquid Colorless strong odor no color change immiscible orange, 5 secs flammable no decolorization decolorized, 5 mins miscible no color change immiscible no precipitate

Liquid colorless strong odor no color change immiscible orange, 6 secs flammable no decolorization decolorized, 7 mins miscible no color change immiscible no precipitate

Liquid colorless strong odor no color change immiscible orange flame, 5 secs flammable no decolorization did not decolorize miscible no color change immiscible no precipitate

Liquid colorless strong odor yellow miscible orange flame, 8 secs flammable no decolorization with brown suspension no decolorization miscible no color change immiscible no precipitate

liquid colorless strong odor yellow miscible orange flame, 3 secs flammable no decolorization with brown suspension decolorized, 10 mins miscible became yellow when added with H2S04 miscible with water black precipitate

References:
www.chemistry.com www.orgchem.colorado.edu www.chemistryabout.com

www.sigmaaldrich.com/chemistry/solvents/produ cts.html? www.chemguide.co.uk/orgpropsmenu.html www.chemistryexplained.com

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