REACTIONS OF HYDROCARBONS

Angel C. Go De La Salle University-Dasmarias Dasmarias City, Cavite, Philippines

ABSTRACT

There are differences between the reactions of saturated hydrocarbon and unsaturated hydrocarbon. Saturated hydrocarbons forms four single covalent bonds with other atoms on its each carbon atom in the molecule. They are single bonded and have greater compliment of hydrogen. Unsaturated carbons are usually double bonded thus; it does not contain the maximum amount of hydrogen. Based on characteristic reactions it will determine hydrocarbons. Addition of strong oxidative reagent like Bayers reagent(basicpotassiumpermanganate) leads to the formation of alcohol for alkenes and carboxylic acids foralkynes. Tollens reagent is a weak oxidizing agent composed of ammoniacal silvernitrate. It reacts with terminal alkynes to form silver alkylides. Halogenation is theaddition of halide substituents like bromine. This occurs via different mechanisms andextent with different hydrocarbons.

INTRODUCTION Hydrocarbons, compounds which contain only carbon and hydrogen, can be classified into several types, depending on their structure. Aliphatic hydrocarbons are divided into three classes: alkanes have only single bonds, and are said to be saturated; alkenes and alkynes have carbon-carbon double or triple bonds, and are said to be unsaturated. Aromatic hydrocarbons are cyclic compounds whose structure is related to that of benzene, with six -electrons in a six-member ring. (1) Aliphatic Hydrocarbons such as Alkanes are relatively inert to chemical oxidizing agents such as neutral or alkaline permanganate, where alkenes are readily oxidized at room temperature. The change in color can be used as a test for a double bond, provided the molecule contains no easily oxidizable group.(2)

MATERIALS AND METHODS

Materials and Reagents used: Hexane Eugenol Calcium carbide Unknown hydrocarbon 1 Unknown hydrocarbon 2 PROCEDURES: Bromine in CCL4 Bayers reagent Distilled water Tollens reagent Pasteur pipettes Screw-capped test tubes Separatory funnel Distilling Flask Iron ring and clamp Rubber tubing and pinchook

Place 5 drops of hexane, eugenol, Acetylene, unknown hydrocarbon 1, Unknown hydrocarbon 2 on separate dry testube . Prepare new set of samples for each of the chemical test

Bayers Test + 5 drops of Bayers regent shake and then observe

Bromination (with light) y y + 5 drops of Bromine Shake and then observe

Bromination (without light) y y y y + 5 drops of Bromine Wrap the testube with paper Place the sample in a dark place for 2min observe

Tollens test y y + 5 drops of Tollens reagent Shake and then observe

Prepare the set-up for acetylene generation Figure 1

Add small increments of water to calcium carbide at a time to initiate the formationof acetylene. Collect acetylene into the test tubes From the results of the tests, identify whether your unknown sample is an alkane,alkene, or alkyne. RESULTS AND DISCUSSIONS The table shows the reactions of hydrocarbons. The samples are the saturated and the unsaturated hydrocarbons. Such as the unknown 1 or cyclohexane is a type of alkene, an unsaturated hydrocarbon. Hexane is an alkane, a saturated hydrocarbon. Acetylene is an ethyne so it is an alkyne. The acetylene reacts with all tests so it is an alkyne. The table represents which sample reacts with the different test if it was a fast, slow or no reaction at all. By doing these test, it will determine wether the sample is an alkane, alkene, or an alkyne. Unsaturated hydrocarbons are more reactive than saturaded hydrocarbons. A. Chemical Test Results Bayers Test Visible + result SAMPLES Hexane Eugenol Acetylene Unknown 1 Unknown 2 Legend: ++ Br2 Test (light) Br2 Test (dark) Tollens Test

+ + fast reaction; +

+ + + + slow reaction; no reaction

+ + + +

+ -

Identities of Unknown Hydrocarbons Sample 1: CYCLOHEXENE(alkene)

Sample 2: HEXANE(alkane) B.Pertinent General Reactions (1)Bayers oxidation: a. ethene ethylene glycol

KMnO4 NaOH

HO

OH

b. ethyne

ethanedioic acid KMnO4

O O

NaOH
HO OH

(2)Bromination (light): a. ethane bromoethane + hydrobromic acid

H H H

H H H

H Br

Br-Br

UV
H H H

HBr

b. ethene
H

trans-dibromoethane
H Br H H H Br

Br-Br

UV
H

c. ethyne

trans-dibromoethene

H H H

Br

Br-Br

UV
Br H

(3)Bromination (dark) a. ethene trans-dibromoethane

H H

Br H

+
H b. ethyne

Br Br

H Br H

HBr

trans-dibromoethene H Br H

Br Br Br

(4)Tollens Test ethyne + silver nitrate H H silver acetylide + nitric acid 2AgNO3 NH3 Ag
+

Ag

2NHO3

ACETYLENE GENERATION: CaC2

2H2O

Ca(OH)2

Structures of Organic Samples Used

CH3

H3C

Figure 2: Hexane Structure 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.(3)

H3C

CH2

HO
Figure 3: Eugenol Structure Eugenol is sometimes called clove oil because it is the active element in cloves. It causes the aromatic smell typical of cloves and because of this property is often found in perfumes. The medical field makes use of Eugenol. Its properties make it a good local antiseptic and analgesic. It also makes a good local anaesthetic for temporary relief from toothache pain. It is used in the production of isoeugenol for the manufacture of vanillin which is an artificial substitute for vanilla.(4)
HC CH

Figure 4: Acetylene Structure Acetylene is a colorless, combustible gas with a distinctive odor. When acetylene is liquefied, compressed, heated, or mixed with air, it becomes highly explosive. As a result special precautions are required during its production and handling. The most common use of acetylene is as a raw material for the production of various organic chemicals including 1,4-butanediol, which is widely used in the preparation of polyurethane and polyester plastics. The second most common use is as the fuel component in oxy-acetylene welding and metal cutting. Some commercially useful acetylene compounds include acetylene black, which is used in certain dry-cell batteries, and acetylenic alcohols, which are used in the synthesis of vitamins.(5)

Figure 5. Cyclohexene Structure This cycloalkene is a colorless liquid with a sharp smell. It is an intermediate in various industrial processes. Cyclohexene is not very stable upon long term storage with exposure to light and air because it forms peroxides.(6) REFERENCES

(1) Legaspi, G. A. and Sta. Ana, S.T. Essentials of Organic Chemistry Laboratory. 2010. Philippines. (2) "Hydrocarbons." Web. 01 Jan. 2012. <http://hyperphysics.phyastr.gsu.edu/hbase/organic/hydrocarbon.html>."Eugenol." Chemicalland21.com ^^. Web. 27
Dec. 2011. <http://www.ChemicalLand21.com>.

(3) "Hexane." Eco-USA. Web. 01 Jan. 2012. <http://www.ecousa.net/toxics/chemicals/hexane.shtml>. (4) "Eugenol." Chemicalland21.com ^^. Web. 27 Dec. 2011. <http://www.ChemicalLand21.com>. (5) "Acetylene - ENotes.com." ENotes - Literature Study Guides, Lesson Plans, and More.Web. 01 Jan. 2012. <http://www.enotes.com/acetylene-reference/acetylene>. (6) Michael T. Musser "Cyclohexanol and Cyclohexanone" in Ullmann's Encyclopedia of Industrial
Chemistry, Wiley-VCH, Weinheim, 2005.doi:10.1002/14356007.a08_217