Preparation and Reactions of Amines

Vocabulary

acylation

process of adding an acyl group to a compound

amide

organic compound that contains a carbonyl (${\rm{C{=}O}}$) linked to a nitrogen atom through a ${ \rm{C{-}N}}$ bond. It has a general ${\rm{RC({=}O)NRR'}}$ stoichiometry.

amination

process of adding an amine group to a compound

amine

organic compound that is a derivative of ammonia (NH3), in which one or more hydrogen atoms are replaced by alkyl or aryl units (R), forming ${\rm{N{-}R}}$ single bonds

aryl diazonium salt

one of a group of salts of the general formula ArN2X, where Ar is an aryl group and X is an anion, such as benzenediazonium chloride (C6H5N(N)Cl)

azide

compound containing the group N3 combined with an element or a radical

azo compound

organic compound bearing the functional group diazenyl ${\rm{R{-}N{=}N{-}R'}}$, in which R and R′ can be either aryl or alkyl

azo coupling

electrophilic aromatic substitution reaction between an aryl diazonium salt and another aromatic compound that produces an azo compound

Curtius rearrangement

reaction that involves the thermal decomposition of acyl azides to produce an isocyanate intermediate, which is then hydrated and decarboxylated to form a primary amine

diazotization

process of converting a primary amine into its diazonium salt

Gabriel synthesis

reaction in which alkyl halides are treated with phthalimide and a strong base, followed by the addition of hydrazine, yielding a primary amine

heterocycle

organic compound containing a ring of atoms of at least two elements (one of which is generally carbon)

Hofmann elimination reaction

process in which the primary amine is treated with excess methyl iodide (CH3I) and then the resultant ammonium salt is distilled under pressure with silver oxide (Ag2O), yielding the least substituted alkene

Hofmann rearrangement

reaction in which primary amides are treated with a halogen and a base and rearranged into an isocyanate intermediate that then converts into a primary amine following the loss of carbon dioxide in the presence of water

imine

organic compound containing the ${\rm {C{=}NH}}$ group or its substituted form, NR, that is derived from ammonia by replacement of two hydrogen atoms by a hydrocarbon group or other nonacid organic group

isocyanate

highly reactive, low-molecular-weight organic compound with the formula ${\rm{R{-}N{=}C{=}O}}$

nitrile

organic compound that has a carbon triple bonded to a nitrogen with RCN stoichiometry

oxime

organic compound containing the divalent group ${\rm{C{=}NOH}}$ and obtained mainly by the action of hydroxylamine on aldehydes and ketones

polyalkylation

reaction that occurs when multiple alkyl groups are added instead of just the desired one alkyl group

reductive amination

two-step form of amination that involves the conversion of a carbonyl group to an amine through an imine (${\rm{C{=}NH}}$) or an oxime (${\rm{C{=}NOH}}$) intermediate

Sandmeyer reaction

replacement reaction that occurs via copper reagents (e.g., CuCl, CuBr, CuCN)