Carbon Compounds

Carbon compounds are the compounds that contain the element carbon. Examples of carbon compounds are plastic, fat, petrol, detergent, protein, amino acids, etc. Due to the varieties of carbon compounds that exist, it is essential to classify them. Carbon compounds can be classified into two categories: inorganic compounds and organic compounds.

Inorganic Compounds
y y y y y In general, inorganic compounds refer to compounds that do not contain the element carbon. Normally, these are the compounds that originate from non-living things. Examples of these compounds are mineral acids, bases, limestone, marble, water and salts. However, there are some exceptions. For instance, carbonates, cyanides and oxides of carbon are categorized as inorganic compounds.

Organic Compounds
y y y y y y Organic compounds are compounds that contain the element carbon as one of their components. Normally, these are the compounds that originate from living things such as plants and animals. Examples of carbon compounds are hydrocarbon, alcohols, carboxylic acids. There are large amounts of known organic compounds. This is due to the fact that the carbon atom can be bonded easily with other carbon atoms as well with different atoms to from new compounds. Carbon has four electrons at the outermost shell. So, the carbon atom uses these atoms to bond with other atoms.

y y y y

The bonding is called covalent bonds. When the carbon atoms are only bonded to hydrogen atoms, the compound is called hydrocarbon. Some organic compounds may contain other elements such as nitrogen, oxygen, sulphur etc. Most of the carbon compounds are known as organic compounds. Examples of organic compound are protein, starch, vitamins, alcohol, etc.

Physical Properties of Organic Compounds

y y y y y y y y y Organic compounds have low melting and boiling points. They do not conduct electricity in the solid, liquid or gaseous states. They also dissolve in water. However, they dissolve in other organic compounds such as in petrol or kerosene.

Hydrocarbons
Hydrocarbons are the simplest organic compounds. They only contain the elements carbon and hydrogen. Hydrocarbon is the main source of fuel for electricity generation and for transportation. Hydrocarbons can be classified into saturated hydrocarbons and unsaturated hydrocarbons depending on the number of bonds they have. See figure below. When there is a single bond between carbon atoms a saturated hydrocarbon is formed whereas multiple bonds between carbon atoms lead to unsaturated hydrocarbons. Saturated hydrocarbons are also known as alkanes. Unsaturated hydrocarbons can be further sub-divided into three categories, namely, alkenes, alkynes and arenes.

y y

Alkanes, alkenes and alkynes are aliphatic hydrocarbons.

y y y

Aliphatic compounds do not contain the benzene ring. They can have a linear or ring structure. Aliphatic hydrocarbons can be unbranched or branched.

Ring Structure of Benzene

Sources and Uses of Hydrocarbon Compounds

The main sources of hydrocarbon are: i. crude oil (petroleum) ii. natural gas iii. coal Petroleum, natural gas and coal are called fossil fuels because they are formed by the decay of organisms which died millions of years ago. Crude oil is a complex mixture of hydrocarbons whereas natural gas consists mainly of methane gas (CH4). Different hydrocarbons have different physical properties. They have different boiling points, melting points, densities, volatilities and colors. For instance, natural gas is lighter than petroleum and will float on top of petroleum. Crude oil is a mixture of different hydrocarbons. Since hydrocarbons have different boiling points, they can be separated using fractionation distillation as shown as in table below:

he fractional distillation of a crude oil

Coal is a complex mixture containing mainly hydrocarbons. Some of the compounds contain the elements nitrogen and sulphur. Destructive distillation is a process when the coal is heated in the absence of air. The fractions obtained from destructive distillation are coal gas, ammonia, coal tar and coke.

Combustion of Organic Carbon Compounds

Hydrocarbons contain only carbon and hydrogen. When complete combustion occurs, where the hydrocarbons are burnt in the presence of air (excess oxygen), only water and carbon dioxide are formed. The element carbon in the hydrocarbon combines with oxygen in the air to form carbon dioxide. The equation is:

The hydrogen in the hydrocarbon combines with oxygen in the air to form water. The equation is:

The overall equation for the combustion of hydrocarbons can be represented as below:

It can be seen that the product of the combustion process is the carbon dioxide and water. Experiment can be conducted to identify the products from the combustion process.

Alkanes
Alkanes are a group of saturated aliphatic hydrocarbons. They only contain carbon and hydrogen. All the carbon-carbon bonds are single bonds. Alkanes have a maximum number of hydrogen atoms bonded to the carbon atoms. The simplest alkane is CH4 (methane) and the next is C2H6 (ethane) followed by C3H8 (propane). The general formula for alkanes is CnH2n+2.

Nomenclature of Unbranched Alkanes

Organic compounds are named according to the IUPAC (the International Union of Pure and Applied Chemistry) system. All members of the alkane series have names ending with -ane. The first part (prefix) of the name of the alkane indicates the number of carbon atoms in the molecule. Table below are the prefixes used and the names of the Prefixes name of alkanes series

Molecular Formula of Alkanes

The molecular formula is a chemical formula that shows the actual number of elements present in a molecule. However, it does not show the arrangement of the atoms in the molecule. Steps to write the molecular formula of alkanes:
y y y

Determine the number of carbon atoms in the straight-chain molecule of the alkane. Select a suitable prefix to show the number of carbon atoms. Add the suffix -ane.

Structural Formula of Alkanes

The structural formula is a chemical formula that shows the number of elements present as well as the arrangement of the atoms and covalent bonds between the atoms in a molecule.
y y

Remember that each carbon atom has four single covalent bonds and each hydrogen atom has only a single covalent bond. Write the carbon chain that contains the carbon atoms, e.g., propane.

Add hydrogen atoms to the carbon atoms so that each carbon atom has four single covalent bonds.

Structural Formula for Series of Alkanes

Table below shows the molecular formula and structural formula for the first ten alkanes. he molecular and structural formulae of alkanes

Physical Properties of Alkanes

Melting and Boiling Point of Alkanes
Alkanes are non-polar compounds. The intermolecular forces between the molecules are weak Van der Waal's forces. Only a little energy is required to break the intermolecular forces. Therefore, the melting and boiling points of alkanes are low. The increase in the number of carbon atoms causes increases in the melting and boiling points. This is due to the larger molecular size. When the molecular size is larger, the Van der Waal's forces between the molecules become stronger. So, more energy is needed to break the intermolecular forces.

Physical States of Alkanes

At room temperature, the first four alkanes exist in gaseous forms. The alkanes from C5C18 are liquids at room temperature. This happens because the boiling points increase when the number of carbon atom increases. Alkanes that contain more than 18 carbon atoms are solids.

Density of Alkanes
All alkanes are less dense than water. The density increases when the number of carbon atoms in the alkanes increases. The density of a substance is the mass/volume. Therefore, when the number of carbon atom increases, the molecular mass increases as well. This causes an increase of intermolecular forces and the molecules are packed close together. Thus, the density increases gradually when the number of carbon atoms increases.

Solubility of Alkanes
All members in the alkane series are insoluble in water. When an alkane is shaken with water in a test tube, two layers of liquids will be formed. The top layer is the alkane due to its lower density compared to water. Alkanes are soluble and miscible in organic solvents such as ether, benzene, tetrachloromethane and so on.

Electrical Conductivity of Alkanes

Alkanes are non-conductors of electricity. This is because alkanes are simple covalent compounds. Alkanes do not contain free moving ions.

Physical Properties for Series of Alkanes

The physical properties of alkanes are shown in table below:

he physical properties of alkanes

Note that each of the alkanes has different physical properties.

Chemical Properties of Alkanes

Alkanes are organic compounds which are unreactive. Alkanes are chemically inert to most reagents at room temperature, for example, acids, alkalis and oxidizing reagents. All alkanes have similar chemical properties due to their similar types of bonds. These are:
y y

C - C bond C - H bond

Combustion Reaction of Alkanes

In the presence of excess oxygen, alkanes burn readily to produce water and carbon dioxide. This is known as complete combustion which can be represented by the equation.

The combustion of alkanes is exothermic, that is, heat is produced during the reaction. Hence, alkanes can be used as fuels. If there is an insufficient supply of oxygen, a luminous flame will be produced. This is due to the glowing carbon particles in the flame. There is not enough oxygen for the carbon atoms in the alkanes to be burnt completely. Subsequently, carbon (black smoke) is produced. Incomplete combustion produces carbon, carbon monoxide and water.

When the molecular size of the alkane increases, that is, when the number of carbon atoms per molecule alkane increases, the percentage of carbon in the alkane molecule increases. This cause:
y y y y y

the alkane to become less difficult to burn the flame becomes more smoky more heat is produced during the combustion

Substitution Reaction of Alkanes

Substitution reaction is a reaction where an atom (or a group of atoms) is replaced by another atom (or a group of atoms). Alkanes undergo substitution reactions with halogen in the presence of ultraviolet light or sunlight. The substitution reactions occur slowly and a mixture of organic compound and hydrogen halide are produced. For example, in the presence of sunlight, methane reacts with chlorine. The hydrogen atoms in methane are substituted by chlorine atoms step by step.

monochloromethane

dichloromethane

tricholoromethane

tetrochloromethane
y

Alkanes react with bromine in a similar way but at a slower rate. Iodine, however, does not react with alkanes.

Effects of Methane in Daily Life

y

Methane is mainly found in natural gas. It is also known as "marsh gas" because it is formed from the bacterial decay of vegetable matter trapped in the marsh and peat swamps. It can be also produced from decaying animal dung and from rubbish buried in landfills. The formation of methane gas by the decomposition of organic matter may cause fires in landfills and peat swamps. However, methane is used as an important fuel. Besides, it can be used to produce synthesis gas by reaction with steam. The synthesis gas is a mixture of carbon monoxide and hydrogen. It is used to manufacture hydrogen for the Haber process to produce ammonia. Synthesis gas can also be used to manufacture methanol and other organic compounds.

Alkenes
Unsaturated hydrocarbons that contain one or more carbon-carbon double bonds in their molecules are called alkenes. The general formula for alkenes is CnH2n, where n= 2, 3, 4... Alkenes are organic compounds that contain carbon-carbon double bonds. It can be a straight chain or branched - chain compounds.

Nomenclature of Alkenes
According to the IUPAC, all members of the alkene series have the names ending with '-ene'. The first part (prefix that shown previously) of the name of alkene indicates the number of carbon atoms in the molecule. Table below are the prefixes used and the name of the first ten alkenes. Prefixes of alkene series

Structural Formula of Alkenes

Steps to write the structural formula of an alkene:
y

Remember that each carbon atom must be bonded to four covalent bonds. This can either be:

Write the carbon chain that contains the carbon atoms. Example: but-2-ene.

y y

Determine the position of the double bond. The number "2" indicates that the double bond is between C2 and C3. Therefore,

Add in the hydrogen atoms so that each carbon atom has four covalent bonds.

Structural Formula for Series of Alkenes

Table below shows the molecular and structural formulae for the first nine alkenes.

he molecular and structural formulae for alkenes

Physical Properties of Alkenes

Melting and Boiling Points of Alkenes
Alkenes are simple covalent molecules. They have low melting and boiling points. Only a small amount is required to break the weak intermolecular forces (Van der Waal's forces) during the melting or boiling process. When going down the alkene series, the number of carbon atoms per alkene molecule increases. The molecular sizes increase as well and they cause the intermolecular forces to become stronger. So, higher energy is needed to overcome the intermolecular forces. Thus, the melting and boiling points increase when the number of carbon atoms increases.

Physical States of Alkenes

The first three alkenes, namely, ethane, propene and butene, are gases at room temperature due to the low boiling points. Alkenes containing five to 15 carbon atoms are colorless liquids at room temperature while the higher alkenes are waxy solid.

Density of Alkenes
Alkenes are less dense than water. Therefore, alkenes will float on top of water when they are mixed. When the number of carbon atoms increases, the densities of the alkenes increase as well. This is because the increasing molecular sizes cause the increase in the intermolecular forces. As a result, they are packed closer and the molecules have a higher mass per volume. Thus, the density of alkenes increases when going down the series.

Solubility of Alkenes
Alkenes are simple covalent molecules. Thus, they are insoluble in water. When an alkene is shaken with water in a test tube, two layers of liquids will be formed. Alkenes will float on top of the water due to their lower density. However, alkenes are readily soluble and miscible in organic solvents.

Electrical Conductivity of Alkenes

Alkanes do not conduct electricity. This is because alkanes are simple covalent compounds. Alkanes do not contain free moving ions.

Physical Properties for Series of Alkenes

The physical properties of alkenes are shown in table below:

he physical properties of alkenes

Chemical Properties of Alkenes

Alkenes contain one or more double bonds in their molecules. Therefore, alkenes are more reactive compared to alkanes.

Addition Reaction of Alkenes

Alkenes contain double bonds between the carbon atoms (C = C). The instability of the double bonds causes the alkenes to be reactive. Alkene tends to undergo addition reactions. During the reactions, the double bonds are broken and two new single covalent bonds are formed. Addition reaction is the reaction in which an unsaturated compound combines with another element or compound to form a new saturated compound.

Alkenes can undergo addition reactions with the following compounds:

y y y y y

Hydrogen (Hydrogenation) Halogens (Halogenation) Hydrogen halide Water (hydration) Acidified potassium manganate (IV) solution

Addition of Hydrogen
The hydrogenation of alkenes will form alkanes. During the reaction, the alkene is passes and hydrogen is passes over nickel or platinum at 200oC. Nickel or platinum acts as the catalyst. Corresponding alkanes will be produced.

For example: C3H6 (g) + H2 (g) C3H8 (g) Hydrogenation is used to produce margarine (solid form) from vegetable oil (liquid form).

Addition of Halogens
During the halogenation process, alkenes react with halogen to form saturated compounds.

Addition of Hydrogen Halides

Alkenes react with hydrogen halides at room temperature to form saturated organic compounds called halogenoalkanes.

Where HX= HBr, HCl or HI

For example,

Hydration
Alkenes react with water when they were passed over phosphoric (V) acid (catalyst) at 300oC and a pressure of 60 atm. Alcohol is produced.

For example:

Addition of Acidified Potassium Manganate (VII) Solution

Oxidation takes place when alkenes react with acidified potassium manganate (VII) solution. Acidified potassium manganate (VII) is prepared by mixing potassium manganate (VII) solution and dilutes sulphuric acid. Hydrochloric acid should not be used to acidify potassium manganate (VII) solution. This is because hydrochloric acid reacts readily with potassium manganate (VII) to produce chlorine. During the oxidation, the purple color of potassium manganate (VII) is decolorized. A saturated compound called diol is formed. This reaction can be used as a chemical test to identify unsaturated compounds.

For example:

Bromination and Chlorination

Bromination
Bromination can be used as a chemical test to identify unsaturated organic compounds. An alkene is passed into liquid bromine; the brown colour of bromine is decolorised immediately. Dibromoalkane (colourless liquid) is formed. For example:

Chlorination
Alkenes can react with chlorine to form dichloroalkanes. The reaction is known as chlorination. For example:

Combustion of Alkenes
In the presence of excess oxygen, alkenes burn completely to produce water and carbon dioxide. Heat is generated during the combustion. Thus the combustion of alkenes are exothermic processes. Again, the general equation of complete combustion is:

Example: C2H4 (g) + 4O2 (g) 2CO2 (g) + 2H2O (l) C4H8 (g) + 12O2 (g) 4CO2 (g) + 4H2O (l) Alkenes burn with yellow flame. The flame is smokier compared to the corresponding alkane. For instance, burning of pentene (C5H10) produces more soot compared to hexane (C5H12). This is due the higher percentage mass of carbon in the alkenes.

Polymerization of Alkenes Resource

Polymerisation is a reaction in which monomers join together to form a polymer. Monomers are small molecules whereas polymers are long chain molecules that contain thousands of monomers joined together by covalent bonds. The polymerisation of alkene is an addition reaction. It can be known as additional polymerisation. Under suitable conditions, ethane undergoes addition polymerisation to form poly (ethane) which are commonly called polythene.

n = 100-1000, depending on the conditions of the reaction. The suitable conditions for the polymerisation of alkenes are: (i) at the temperature of 200oC and pressure of 1500-2000 atm without a catalyst

(ii) at the temperature of 60-100oC and pressure of 7-10 atm in the presence of a Ziegler catalyst. Propene also undergoes polymerisation to form poly (propene), a harder and more resistant plastic compared to poly (ethene).

Comparison between Alkanes and Alkenes

Physical Properties
Comparison of Physical Properties Between Alkanes and Alkenes

Chemical Properties
Comparison of Chemical Properties Between Alkanes and Alkenes

Homologous Series
A homologous series is a group of organic compounds with the same general formula. Examples of organic compounds in the homologous series are alkanes, alkenes, alcohols, carboxylic acid, esters, etc. All the compounds in the series have the same functional groups, for example, the functional group for alcohol is -OH and the functional group of carboxylic acid is -COOH. As the functional group determines the chemical properties of organic compounds, all the compounds in the series have the same chemical properties. Each member in the series has a different number of carbon atoms and thus has a different length of the carbon chain. However, the different number in the length of the chain does not affect the chemical properties. The different length of the carbon chains only affects the physical properties. The characteristics of the homologous series are as follows:

he general formula
All members in the series have the same general formula.

he preparation method
All members in the series are prepared in a similar way.

Physical properties
Depending on the increasing or decreasing number of carbon atoms, the members in the series exhibit gradual changes in their physical properties (melting and boiling points).

Chemical properties
All members in the group have the same chemical properties. This is because each member has the same functional group.

he molecular formula
Members in the series differ from each other by the -CH2 group.