Addition reaction

An addition reaction, in organic chemistry, is in its simplest terms an organic reaction where two or more molecules combine to form a larger one (the adduct).[1][2]

Addition of chlorine to ethylene

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), and compounds that have rings, which are also considered points of unsaturation. 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

Depending on the product structure, it could promptly react further to eject a leaving group to give the addition–elimination reaction sequence.

References
  1. Morrison, R. T.; Boyd, R. N. (1983). Organic Chemistry (4th ed.). Boston: Allyn and Bacon. ISBN 0-205-05838-8.
  2. March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.), New York: Wiley, ISBN 0-471-85472-7.
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