Functional Groups and their Reaction Mechanisms

 

Functional Group Examples Reaction Mechanism
Alkanes   Free radical Substitution
Alkenes   Electrophilic addition
Alkynes   Electrophilic addition
Dienes   Electrophilic addition
Arenes   Electrophilic aromatic substitution
Alkyl halides   Nucleophilic Substitution

OR

Elimination

Aryl halides   Electrophilic aromatic substitution

OR

Nucleophilic aromatic substitution

Alcohols   Dehydration

OR

Conversion to alkyl halides OR

Esterification

Phenols   Electrophilic aromatic Substitution
Ethers   Cleavage by hydrogen halide
Epoxides   Nucleophilic ring opening
Aldehydes   Nucleophilic addition to carbonyl group
Ketones   Nucleophilic addition to carbonyl group
Carboxylic Acids   Ionization of carbonyl

OR

Esterification

Acyl halides   Nucleophilic acyl substitution
Acid anhydrides   Nucleophilic acyl substitution
Esters   Nucleophilic acyl substitution
Amides   Nucleophilic acyl substitution
Amines   Nitrogen acts as a nucleophile or as a base
Nitriles   Nucleophilic addition to carbon nitrogen triple bond
Nitro Compounds   Reduction of nitro group to amine
Thiols   Oxidation to sulfenic, sulfinic or sulfonic acid