amines
TRANSCRIPT
ObjectivesUnderstand the properties of aminesName and write the formula of amines
AminesAminesAmines are compounds in which one or more
of the hydrogens of ammonia have been replaced by alkyl group.
Smaller amines are characterized by their fishy odors.
There are primary amines, secondary amines and tertiary amines which depends on how many alkyl group are bonded to the nitrogen.
AminesAminesThe smell of fertilizers or decaying plant
matter is characteristic of nitrogen-containing compounds, found, for example, in a pile of mulch.
AminesAmines R – NH2 primary
R- NH –R secondary
tertiaryN R
R
R
AminesAliphatic amines are amines in which
nitrogen is bonded only to alkyl groups.Aromatic amines are amines in which
nitrogen is bonded to one or more aromatic rings.
Common NomenclatureCommon NomenclatureIn common nomenclature, an amine is named
by appending the suffix amine to the name of the alkyl group; the name of the alkyl group bonded to the nitrogen is cited in alphabetical order; the name of the amine is written in one word.
Common NomenclatureCommon NomenclatureCH3 CH2 NH2
N
CH3
CH3
CH3
Ethylamine
Trimethylamine
Common NomenclatureCommon NomenclatureWhen two or more alkyl groups in secondary
or tertiary amine are different, the compound is named as an N-substituted derivative of the larger group.
This type of notation is required to show that the substituents are on the amine nitrogen and not on the alkyl group carbon.
Common NomenclatureCommon Nomenclature
N
CH3
CH2CH2CH2
CH3
CH3
NHCH2CH3N,N-Dimethylbutanamine
N-ethylcyclohexanamine
Common NomenclatureCommon NomenclatureAromatic amines are named as derivative of
aniline.
NH2
Aniline
Common NomenclatureCommon NomenclatureNH2
O2N NHCH2CH3
2-Nitroaniline or o-nitroaniline
N- ethylaniline
Substitutive NomenclatureSubstitutive NomenclatureThe IUPAC System uses a suffix to denote the
amine functional group. This method is similar to the way in which
alcohols are named. The “e” at the end of the name of the parent
hydrocarbon is replaced by “amine”.
Substitutive NomenclatureSubstitutive Nomenclature
CH3 CH2 CH2 CH CH3
NH2
CH34CH23
CH22
CH21
NH2
Substitutive NomenclatureSubstitutive Nomenclature
CH31CH22
CH3
CH24
CH25
NH CH2 CH3
CH36
CH21
CH22
CH23
CH24
CH25
NH2NH2
Substitutive NomenclatureSubstitutive NomenclatureAll substituents (regardless of whether they
are attached to the nitrogen or to the parent hydrocarbon) are listed in alphabetical order.
The chain is numbered such that the functional group suffix gets the lowest possible number.
Substitutive NomenclatureSubstitutive Nomenclature
CH34CH3
CH22
CH21
NH CH3
Cl
CH31
CH22
CH3
CH24
CH5
CH36
NH CH2 CH3
CH3
Substitutive NomenclatureSubstitutive Nomenclature
CH31CH2
CH23
CH4
CH35
Br
N CH3CH3
Substitutive NomenclatureSubstitutive NomenclatureThe priority citation of amine group as
principal groups is just below that of alcohols (recall the hierarchy of the functional group of organic compounds).
When cited as substituent, the –NH2 group is called the amino group.
Substitutive NomenclatureSubstitutive NomenclatureNH2 CH2CH2 OH
CH2 CH CH2 NH2
N CH2CH2
CH3
CH3
CH2 OH