Addition reaction

Addition of chlorine to ethylene

An addition reaction, in organic chemistry, is in its simplest terms an organic reaction where two or more molecules combine to form the larger one (the adduct).

Addition reactions are limited to chemical compounds that have multiple bonds, such as molecules with carbon–carbon double bonds (alkenes), or with triple bonds (alkynes). Molecules containing carbon—hetero double bonds like carbonyl (C=O) groups, or imine (C=N) groups, can undergo addition, as they too have double-bond character.

An addition reaction is the reverse of an elimination reaction. For instance, the hydration of an alkene to an alcohol is reversed by dehydration.

There are two main types of polar addition reactions: electrophilic addition and nucleophilic addition. Two non-polar addition reactions exist as well, called free-radical addition and cycloadditions. Addition reactions are also encountered in polymerizations and called addition polymerization.

General overview of addition reactions. Top to bottom: electrophilic addition to alkene, nucleophilic addition of nucleophile to carbonyl and free-radical addition of halide to alkene

Addition-elimination reaction

In the related addition-elimination reaction an addition reaction is followed by an elimination reaction. In the majority of reactions it involves addition of nucleophiles to carbonyl compounds in what is called nucleophilic acyl substitution.

Other addition-elimination reactions are the reaction of an aliphatic amine to an imine and an aromatic amine to a Schiff base in alkylimino-de-oxo-bisubstitution. The hydrolysis of nitriles to carboxylic acids is also a form of addition-elimination.