Substitution, Addition and Elimination Reactions

Introduction:

Substitution, addition, and elimination reactions are of great importance in a major branch of chemistry known as Organic Chemistry, which covers the chemistry of compounds of carbon. These reactions, which generally involve covalently bonded molecules, are also found, to a much more limited extent with other compounds.

Substitution reactions:

A substitution reaction is a reaction in which an atom (or group of atoms) in a molecule is replaced by another atom or group of atoms:

Example 1:

The gas ethane, CH₃CH₃ reacts with bromine vapour in the presence of light to form bromoethane, CH₃CH₂Br and hydrogen bromide, HBr. In the process, a hydrogen atom in ethane has been substituted for a bromine atom:

Example 2:

Ethanol, CH₃CH₂OH, reacts with hydrogen iodide, HI, to form iodoethane and water. Here, a group of atoms, OH, has been replaced by an iodine atom:

Example 3:

Benzene, C₆H₆, reacts with bromine in the (presence of iron bromide as catalyst) to form bromobenzene, C₆H₅Br. This results in a hydrogen atom being replaced by a bromine atom:

Addition reactions:

An addition reaction is a reaction whereby a molecule reacts with another molecule having one or more multiple covalent bonds so as to form a molecule whose molecular mass is the sum of the molecular masses of the reacting molecules:

Example 3:

Ethene, CH₂=CH₂ has a double bond joining the two carbon atoms. This substance can add a hydrogen molecule (in the presence of platinum as catalyst) to form ethane, CH₃CH₃:

Example 5:

Ethyne, C₂H₂ has a triple bond joining the two carbon atoms. Hydrogen bromide adds onto this triple bond to form 1,1-dibromoethane, CH₃CHBr₂:

Elimination reactions:

An elimination reaction is a reaction whereby a multiple covalent bond is formed in a molecule by the removal of another, usually smaller molecule:

Example 6:

Ethanol, CH₃CH₂OH, when treated with concentrated sulphuric acid, H₂SO₄, loses 2 hydrogen atoms and one oxygen atom, forming ethene, CH₂=CH₂ and water (the atoms that have been eliminated are shown in red):

When an elimination reaction removes the elements of water from a compound, as in the reaction above, the reaction is called a DEHYDRATION REACTION.

Example 7:

Bromoethene, CH₂=CHBr, when treated with potassium hydroxide dissolved in ethanol, loses one hydrogen atom and one bromine atom, forming ethyne, CH≡CH (the atoms that have been eliminated are shown in red):

When an elimination reaction removes the elements of a halogen acid (HCl, HBr, HI) from a compound, as in the reaction above, the reaction is called a DEHYDROHALOGENATION REACTION.