HYDROCARBON

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons from which one hydrogen atom has been removed are functional groups, called hydrocarbyls. Aromatic hydrocarbons (arenes), alkanes, alkenes, cycloalkanes and alkynes -based compounds are different types of hydrocarbons. The majority of hydrocarbons found naturally occur in crude oil, where decomposed organic matter provides an abundance of carbon and hydrogen which, when bonded, can catenate to form seemingly limitless chains.

TYPES OF HYDROCARBONS:The classifications for hydrocarbons defined by IUPAC nomenclature of organic chemistry are as follows: 1. Saturated hydrocarbons (alkanes) are the simplest of the hydrocarbon species and are composed entirely of single bonds and are saturated with hydrogen. The general formula for saturated hydrocarbons is CnH2n+2 (assuming non-cyclic structures). Saturated hydrocarbons are the basis of petroleum fuels and are found as either linear or branched species. Hydrocarbons with the same molecular but different structural formulae are called structural isomers. As given in the example of 3-methylhexane and its higher homologues, branched hydrocarbons can be chiral. Chiral saturated hydrocarbons constitute the side chains of biomolecules such as chlorophyll and tocopherol. 2. 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 calledalkynes, with general formula CnH2n-2. 3. Cycloalkanes are hydrocarbons containing one or more carbon rings to which hydrogen atoms are attached. The general formula for a saturated hydrocarbon containing one ring is CnH2n. 4. Aromatic hydrocarbons, also known as arenes, are hydrocarbons that have at least one aromatic ring. Hydrocarbons can be gases (e.g. methane and propane), liquids (e.g. hexane and benzene), waxes or low melting solids (e.g. paraffin waxand naphthalene) or polymers (e.g. polyethylene, polypropylene and polystyrene).

GENERAL PROPERTIES:Because of differences in molecular structure, the empirical formula remains different between hydrocarbons; in linear, or "straight-run" alkanes, alkenes and alkynes, the amount of bonded hydrogen lessens in alkenes and alkynes due to the "self-bonding" or catenation of carbon preventing entire saturation of the hydrocarbon by the formation of double or triple bonds. This inherent ability of hydrocarbons to bond to themselves is referred to as catenation, and allows hydrocarbon to form more complex molecules, such as cyclohexane,and in rarer cases, arenes such as benzene. This ability comes from the fact that bond character between carbon atoms is entirely non-polar, in that the distribution of electrons between the two elements is somewhat even due to the same electro negativity values of the elements (~0.30), and does not result in the formation of an electrophile. Generally, with catenation comes the loss of the total amount of bonded hydrocarbons and an increase in the amount of energy required for bond cleavage due to strain exerted upon the molecule; in molecules such as cyclohexane, this is referred to as ring strain, and occurs due to the "destabilized" spatial electron configuration of the atom. In simple chemistry, as per valence bond theory, the carbon atom must follow the "4hydrogen rule, which states that the maximum number of atoms available to bond with carbon is equal to the number of electrons that are attracted into the outer shell of carbon. In terms of shells, carbon consists of an incomplete outer shell, which comprises 4 electrons, and thus has 4 electrons available for covalent or dative bonding. Hydrocarbons are hydrophobic and are lipids. Some hydrocarbons also are abundant in the solar system. Lakes of liquid methane and ethane have been found on Titan, Saturn's largest moon, confirmed by the Cassini-Huygens Mission. Hydrocarbons are also abundant in nebulae forming polycyclic aromatic hydrocarbons - PAH compounds.

USAGE:Hydrocarbons are one of the Earth's most important energy resources. The predominant use of hydrocarbons is as a combustible fuel source. In their solid form, hydrocarbons take the form of asphalt. Mixtures of volatile hydrocarbons are now used in preference to the chlorofluorocarbons as a propellant for aerosol sprays, due to chlorofluorocarbon's impact on the ozone layer. Methane [1C] and ethane [2C] are gaseous at ambient temperatures and cannot be readily liquefied by pressure alone. Propane [3C] is however easily liquefied, and exists in 'propane bottles' mostly as a liquid. Butane [4C] is so easily liquefied that it provides a safe, volatile fuel for small pocket lighters. Pentane [5C] is a clear liquid at room temperature, commonly used in chemistry and industry as a powerful nearly

odorless solvent of waxes and high molecular weight organic compounds, including greases. Hexane [6C] is also a widely used non-polar, non-aromatic solvent, as well as a significant fraction of common gasoline. The [6C] through [10C] alkanes, alkenes and isomeric cycloalkanes are the top components of gasoline, naphtha, jet fuel and specialized industrial solvent mixtures. With the progressive addition of carbon units, the simple non-ring structured hydrocarbons have higher viscosities, lubricating indices, boiling points, solidification temperatures, and deeper color. At the opposite extreme from [1C] methane lie the heavy tars that remain as the lowest fraction in a crude oil refining retort. They are collected and widely utilized as roofing compounds, pavement composition, wood preservatives (the creosote series) and as extremely high viscosity sheer-resisting liquids.

CRACKING HYDROCARBONS
INTRODUCTION:In this experiment the vapour of liquid paraffin (a mixture of saturated hydrocarbons) is cracked by passing it over a heated catalyst. The mixture of gaseous short-chain hydrocarbons produced is collected and tested for unsaturation with bromine water and acidified potassium manganate(VII) solution. This experiment is intended as a class practical, but could also be done as a demonstration. The main risk to be considered in making the choice is the reliability of the students involved in handling very hot glassware and manipulating the apparatus for the safe collection of the flammable gas mixture over water. As a class practical, it is best if the students work in pairs, with one student controlling the Bunsen burner and the other collecting the tubes of gas. Students not familiar with using bromine water and potassium managanate(VII) solution to test for unsaturation need to be taught these tests first, using cyclohexane,and cyclohexene. The class experiment should take about 45 minutes. A demonstration will take take about 15 - 20 minutes, including testing of the gases.

APPARATUS:Eye protection Safety screens (for demonstration) Test-tubes, 4 Bungs, to fit test-tubes, 4 Test-tube rack Boiling tube (Note 1) Bung, one-holed, to fit boiling tube Delivery tube fitted with a Bunsen valve (Note 2) Small glass trough or plastic basin, for gas collection over water Bunsen burner Heat resistant mat

Stand and clamp Dropping pipette Wooden splint

CHEMICALS USED:Medicinal paraffin (Liquid paraffin - NOT the fuel), about 2 cm3 Porous pot or pumice stone fragments (Note 3) Bromine water, 0.01 M - diluted to a pale yellow-orange colour (HARMFUL), about 2 cm3 Acidified potassium manganate(VII) solution, about 0.002 M, about 2 cm3 Mineral wool (preferably 'Superwool') Refer to Health & Safety and Technical notes section below for additional information.

HEALTH & SAFETY AND TECHNICAL NOTES:Wear safety goggles. Medicinal paraffin (Liquid paraffin) - see CLEAPSS Hazcard. Bromine water, Br2(aq) (HARMFUL) - see CLEAPSS Hazcard and CLEAPSS Recipe Book. Dilute the bromine water until it is pale yellow-orange in colour. Note that above Acidified potassium manganate(VII) (potassium permanganate) solution, KMnO4(aq) see CLEAPSS Hazcard and CLEAPSS Recipe Book. Mineral wool (preferably 'Superwool') - see CLEAPSS Hazcard. 1. The boiling tube should be a hard glass (borosilicate) 150 mm x 25 mm test-tube. 2. It is important to ensure that the bung and the boiling tube fit well. Bunsen valves (see diagram below) can be made by attaching a 3 cm long piece of clean, unused, soft rubber tubing to the delivery tube, and then attaching a short length (1 - 2 cm) of glass rod, as shown in the diagram below. The rubber tubing should be slit on one side along about 1 cm of its length in the direction of the tubing. The use of a Bunsen valve should stop 'suck-back' occurring. See CLEAPSS Laboratory Handbook 13.2.1.

3. Porous pot chips can be made by crushing broken crucibles into pea-sized fragments.

PROCEDURE:For a demonstration the class and teacher should be protected by safety screens in case of unexpected suck-back causing the hot tube to shatter. 1. Place about a 2 cm3 depth of mineral wool in the bottom of the boiling tube and gently press it in place with a glass rod. Drop about 2 cm3 of liquid paraffin on to the wool, using a dropping pipette, Use enough paraffin to completely soak the mineral wool, but not so much that the paraffin runs along the side of the tube when it is placed horizontally. 2. Clamp the boiling tube near the mouth so that it is tilted slightly upwards, as shown in the diagram below. Place a heap of catalyst (pumice stone or porous pot fragments) in centre of the tube and fit the delivery tube.

3. Fill the trough about two-thirds full with water and position the apparatus so that the end of the delivery tube is well immersed in the water. 4. Fill four test-tubes with water and stand them inverted in the trough. Also place the test-tube bungs, upside down, in the water.

5. Strongly heat the catalyst in the middle of the tube for a few minutes, until the glass is up to a dull red heat. Avoid heating the tube too close to the rubber bung. 6. While keeping the catalyst hot, flick the flame from time to time to the end of the tube for a few seconds to vaporize some of the liquid paraffin. Try to produce a steady stream of bubbles from the delivery tube. Be careful not to heat the liquid paraffin too strongly or let the catalyst cool down. To avoid suck-back do not remove the flame from heating the tube while gas is being collected. If suck-back looks as if it is about to occur, lift the whole apparatus by lifting the clamp stand. 7. When a steady stream of gas bubbles is established, collect four tubes full of gas by holding them over the Bunsen valve. Take care not to lift the water-filled tubes out of the water when moving them, to avoid letting air into them. Seal the full tubes by pressing them down on the bungs, then place them in a rack. 8. When gas collection is complete, first remove the delivery tube from the water by tilting or lifting the clamp stand. Only then stop heating. (i) Test the tubes of gas as follows: 1. What does the gas look like? Carefully smell the contents of the first test-tube. Of what does the smell remind you? Does liquid paraffin have a smell? 2. Use a lighted splint to see if the gas is flammable. The first tube may contain mostly air. If it does not ignite, try the second tube. Once the gas is lit, invert the test-tube to allow the heavier-than-air gas to flow out and burn. 3. To the third tube of gas add 2 - 3 drops of bromine water, stopper and shake well. 4. To the fourth tube add 2 - 3 drops of acidified potassium manganate(VII) solution, stopper and shake well.

TEACHING NOTES:The demand for petrol is greater than the gasoline fraction obtained by distilling crude oil. Cracking larger hydrocarbons produces smaller alkanes that can be converted into petrol. It also produces small alkenes, which are used make many other useful organic chemicals (petrochemicals), especially plastics. This experiment models the industrial cracking process. You need to be particularly vigilant and lift the apparatus out of the water if suck-back starts to occur and cannot be reversed by stronger heating. It is very important to stress that students should not stop heating the boiling tube at the end of the experiment until the delivery tube is out of the water and contains no water.

The gas mixture which collects has a characteristic smell, burns with a yellow flame, and decolourises bromine water and acidified potassium manganate(VII) solution. This shows the presence of unsaturated molecules. Students will find it helpful to build molecular models to understand the reaction and be able to write an equation for the reaction.

WEBLINKS:There are many, but few deal with this topic at the level at a level appropriate to 14 - 18 chemistry teaching and learning - most are either far too technical or too elementary. Chemguide - a discussion of the cracking of hydrocarbons for A-level chemistry students and teachers. Wikipedia - a good overview of industrial processes for hydrocarbon cracking.