Nomenclature of Organic compounds Organic compounds are named according to the IUPAC system naming.

. Entire name of organic compound has 3 portions:

Prefix + root + Suffix

1.

It is important to remember that each chain, branch (chain side) or ring has name based on the number of carbon atom (C). If the compound has no branch, the name of the compound will consist of the root and the suffix. Identify the parent hydrocarbon (root) Select the longest continuous carbon chain that contains functional group. Identify the number of carbon in this longest continuous chain. Identify and indicate the position of functional group. (Suffix) gives the functional group the lowest possible numbers if the chain forms a ring, the name is preceded by cycloName the branch or side chain. (Prefix) Alkyl group are named by replacing the ane suffix of alkane with yl The ending yl signifies that it is not part of the main chain. Alkyl group is an alkane from which 1 H atom has been removed If more than one side chains are present, prefixes such as (2) di-, (3) tri-, (4) tetra-, (5) penta-, (6) hexa- are been used. If two or move types of branches are present, name them in alphabetical order.

2.

3.

A) Alkanes 1. Alkanes are members of a family hydrocarbon in which each carbon atom is bonded to four other atoms by a single covalent bonds. 2. Alkanes are saturated compound. 3. General Formula: CnH2n+2 n= 1,2,3,4. 4. All members of the alkanes series have their names ending with -ane Number of carbon atom, n 1 2 3 4 5 Root name Meth Eth Prop But Pent Number of carbon atom, n 6 7 8 9 10 Root name Hex Hept Oct Non Dec

Example: When n=1 Name = methane Molecular formula = C1H2(1)+2 = C1H4 or CH4 Structural Formula: H H C H H 5. Each carbon atom is bonded to other atoms by 4 single covalent bonds. 6. Each hydrogen atom should have one single covalent bond. 7. Alkanes are called saturated compounds because all the valence electrons are used up to form 4 single covalent bonds with other atoms. Molecular formula n=1 Structural formula Molecular formula n=3 Structural formula

n=2

n=4

Structural formula is the chemical formula that shows the arrangement of atoms and covalent bonds between atoms in a molecule of the compound

8. Physical Properties of alkanes Molecular Mr formula CH4 16 Melting & boiling point
(low) increasing

Physical Density state gas

(low) (less than water)

Solubility in water
All insoluble in water (because covalent compound

Conductivity of electricity
All do not conduct electricity

liquid

increasing

There is a difference of CH2 between successive members. Hence, the relative molecular mass increases 14 between successive members. The molecular size of alkanes increases when going down the series. Melting point and boiling point of alkanes are low Reason: Molecules are attracted together by the weak forces of attaraction (van der waals). Only small amount of heat energy is needed to overcome the weak forces of attraction during melting and boiling. When descending the series, the melting and boiling point increases. Reason: The number of carbon and hydrogen atoms per molecule increases, molecular size increases. Hence, the forces of attraction between molecules become stronger, more heat energy is required to overcome the forces. Density of alkanes are low The densities increases gradually when going down the series because the molecular size increases, the forces of sttraction between molecules become stronger. Thus, the molecules are packed closer together. All alkanes members are insoluble in water. This is because alkanes are covalent compounds. All alkanes members are soluble in organic solvent (example in ether, benzene, toluene)

The color of alkanes becomes darker when go down the series. All alkanes members do not conduct electricity. This is because they are covalent compound, do not have free moving ions.

9. Chemical properties Each carbon atom in an alkane molecule is already bonded to a maximum number of atoms. Alkanes are saturated compounds. Alkanes contain the C-C and C-H single covalent bonds. These single covalent bond are strong and not reactive. Thus, alkanes are hydrocarbons that are less reactive compared to unsaturated hydrocarbon. Alkanes are unreactive compounds. For example: Alkanes do not react with chemicals such as acids, alkalis, oxidizing agents and reducing agents at room temperature. Alkanes are neutral compounds. Although alkanes do not react with most chemicals, they do react with oxygen and halogens. a. Combustion of alkanes Alkanes burn readily in air i. Complete combustion (sufficient / excess oxygen gas) Produce carbon dioxide gas, water and a lot of heat Chemical equation: Incomplete combustion (insufficient oxygen gas) Produce carbon (black smoke), carbon monoxide, water and a little heat. Alkanes burn with a sooty flame Chemical equation: Or

ii.

Activity 1: 1. Write the chemical equation for the combustion of ethane. a. Complete combustion: .. b. Incomplete combustion: .. 2. Calculate the volume of carbon dioxide gas produced in room condition when 20cm3 of ethane gas is burnt completely in air. [molar volume: 24 dm3 in room conditions]

When going down alkanes series, alkanes become less flammable, that is, more difficult to burn the flame becomes more smoky the alkanes produces more heat on combustion reason: The number of carbon atoms per molecule increase / percentage of carbon by mass in alkanes increase. Example: Calculate the percentage of carbon according to mass in ethane and propane Ethane: C2H6 % of carbon = = 80%

b) Substitution reactions Alkanes can react with halogen through substitution reaction. The reaction is also called Halogenation. The reaction only occurs with the presence of sunlight or ultraviolet light. Substitution reaction is the reaction occurs when one atom or a group of atoms in a molecule is replaced by another atom or group of atoms. Example: Under room conditions and in the absence of ultraviolet light, methane does not react with chlorine. However, when a mixture of methane and chlorine is exposed to sunlight or ultraviolet light, substitution reaction occurs slowly and a mixture of organic compounds and hydrogen chloride is produced. In the reaction between methane and chlorine, the hydrogen atoms in methane are replaced step by step by chlorine atoms. Stage 1: H H C H Stage 2: H H C H Cl + L Cl2
sunlight

H H + Cl2
sunlight

C H

Cl

HCl

Chloromethane

Cl H C H Cl + HCl

dichloromethane

Stage 3: Cl H C H Stage 4: Cl H C Cl Cl L + Cl2

sunlight

Cl Cl + L Cl2
sunlight

C Cl

Cl

HCl

trichloromethane

Cl Cl C Cl Cl + HCl

tetrahloromethane

Overall chemical equation:

10. Isomerism isomerism is the existence of two or more compounds that have the same molecular formula but different structural formulae. Isomers are molecules which have the same molecular formula but different structural formulae. Means, each isomer has a different arrangement of atoms in space. Methane, ethane, and propane do not show isomerism. The fourth and subsequent members of the alkanes series have isomers. Alkane Butane Pentane Number of isomer 2 3

Activity 2: Write the structural formulae of isomers of pentane and name the isomers. How to name the isomers? Name of chain side Formula of alkyl Name group -CH3 Methyl -C2H5 Ethyl -C3H7 Propyl

Formula of alkyl group -Cl -Br -I

Name Chloro Bromo Iodo

Steps:

1. 2. 3. 4.

Identify the parent chain (longest carbon chain) * The carbon atoms in the longest continuous chain do not necessarily have to be in a straight line. Identify the alkyl group in the side chain Identify the position of the alkyl group Combine the name of the side chain with the name of parent chain.

Example: Butane; C4H10

name: ..

side chain name: . parent chain (longest continuous carbon chain)

* If two or more of the same kind of alkyl groups are attached to the same chain, the number of alkyl groups is indicated by the prefixed: di-(2), tri-(3), tetra-(4) and so on.

B) Alkene 1. Alkenes are members of a family of hydrocarbons containing at least one double bond between carbon atom. 2. Alkenes are unsaturated hydrocarbons 3. General formula: CnH2n n=2, 3, 4, 4. All members of the alkenes series have their names ending with -ene 5. Physical Properties of alkanes Molecular Mr formula C2H4 28 Melting & boiling point
(low) increasing

Physical Density state gas

(low) (less than water)

Solubility in water
All insoluble in water (because covalent compound

Conductivity of electricity
All do not conduct electricity

liquid

increasing

solid

There is a difference of CH2 between successive members. Hence, the relative molecular mass increases 14 between successcive members. The molecular size of alkenes increases when going down the series. Melting point and boiling point of alkenes are low reason: Molecules are attracted together by the weak forces of attraction (van der waals) When descending the series, the melting and boiling point are increases. reason: The number of carbon and hydrogen atoms per molecule increase, molecular size increase. Hence the forces of attraction between molecules become stronger, more heat energy is required to overcome the forces. Density of alkenes are low (less dense then water) densities increases gradually when going down the series because the molecular size increases, the force of attraction between molecules becomes stronger. This causes the molecules to be packed closer and the molecules become heavier.

6.

Chemical properties of alkenes Alkenes are neutral. Alkenes are unsaturated hydrocarbon compound. Alkenes are chemically more reactive than alkanes due to the presence of the carbon-carbon double bond. Besides combustion, alkenes react with substances such as hydrogen, halogens, hydrogen halides, water and acidified potassium manganate (VII). alkenes also undergo polymerization. a) Combustion of alkenes Alkenes burn readily in air Complete combustion (in sufficient / excess oxygen gas) Produce carbon dioxide gas, water and a lot of heat. Example: Complete combustion of ethane and propene Chemical Equation: Incomplete combustion of alkenes (insufficient oxygen gas) Produce carbon (black smoke), carbon monoxide, water and little heat. alkenes burn with a sooty flame Example: Incomplete combustion pf ethane and propane Chemical equation: When going down alkenes series, the alkenes become less flammable, that is, more difficult to burn the flame becomes more smoky the alkenes produces more heat on combustion alkenes burn with sootier flames (smoky) than the corresponding alkanes reason: Alkenes have a higher percentage of carbon according to mass in their molecules than alkanes Example: Combustion of hexene is more luminous and smoky than hexane Calculation: Hexene: % of C = Hexane: % of C =

b) Addition reaction of alkenes Alkenes tend to undergo addition reaction. During addition reactions, each carbon-carbon double bond breaks open to form two new single bonds. Means, unsaturated compound is converted to a saturated compound. Example: Hydrogenation (+H2) Example:

Halogenation (+Br2 or Cl2) Example:

The brown color of bromine is decolorized This reaction can occur in the dark.

reaction with hydrogen halides (HCl, HBr, HI) Example:

Hydration (+steam, H2O) Example:

A mixture of ethane and steam is passed over phosphoric (V) acid. H3PO4 as a catalyst at 300OC and apressure of 60 atmosphere.

reaction with acidified potassium manganate (VII) solution, KMnO4 Example:

The purple color of KMnO4 is decolorized.

polymerization of alkenes Type of polymerization: addition Example: Hundreds or thousands of the ethene molecules link together to form long chain called polyethene.

Activity: Write the chemical equation for the polymerization of propene 7. Isomerism in alkenes In the homologous series of alkenes, ethane and propene do not have isomers. Isomerism in alkenes is caused by a) the position of the carbon-carbon double bond in the molecule and b) the different carbon chains in the alkene molecule Alkene Butane Pentane Number of isomer 3 5

Activity 5: Draw the structural formulae and give name of all the isomers of butane Structural Formulae Name

How to name the isomers? Step 1: Identify the parent alkene Step 2: Determine the position of the double bond Step 3: Identify the alkyl group and its position Step 4: Name the alkene

C)

Comparing properties of alkanes and alkenes 1. 2. Physical properties are quite similar but differ in chemical properties. Alkenes are chemically more reactive than alkanes. Alkane Insoluble Produce CO2 + H2O Less sooty The brown color of bromine liquid remains unchanged The purple color of KMnO4 remains unchanged Alkene Insoluble Produce CO2 + H2O More sooty The brown color of bromine liquid is decolorized The purple color of KMnO4 is decolorized

Chemical test Solubility in water Combustion Br2 liquid (brown) Acidified KMnO4 (purple) 3. The i) ii) iii)

reactions that can be used to distinguish between alkane and alkene are Sootiness of combustion Reaction with bromine liquid Reaction with acidified KMnO4