13.1 Write IUPAC names of the following compounds and classify them into primary, secondary, and tertiary amines.
(i) (CH3)2CHNH2
(ii) CH3(CH2)2NH2
(iii) CH3NHCH(CH3)2
(iv) (CH3)3CNH2
(v) C6H5NHCH3
(vi) (CH3CH2)2NCH3
(vii) m–BrC6H4NH2
Step 1:
Amines are classified as primary (1o ), secondary (2o ) and tertiary (3o ) depending upon the number of hydrogen atoms replaced by alkyl or aryl groups in ammonia molecule.
If one hydrogen atom of ammonia is replaced by R or Ar , we get RNH2 or ArNH2 , a primary amine (1o ) is obtained.
If two hydrogen atoms of ammonia or one hydrogen atom of R-NH2 are replaced by another alkyl/aryl(R’) group then
R-NHR’, the secondary amine is obtained as a product.
If all the hydrogen atom is replaced by an alkyl/aryl group then tertiary amine is obtained as a product.
Step 2:
(i)
The molecular formula of the given compound is (CH3)2CHNH2 . The structure is as follows:
The parent chain contains three carbon atoms. The carbon-containing -NH2 group gets the lowest position. The structure with the numbering is as follows:
The IUPAC name of the compound is propan-2-amine and the amine is primary because only one alkyl group is attached to a nitrogen atom.
(ii)
The molecular formula of the given compound is CH3(CH2)2NH2. The structure is as follows:
The longest carbon chain contains three carbon atoms. The structure with numbering is as follows:
The IUPAC name of the compound is propanamine and the amine is primary because only one alkyl group is attached to a nitrogen atom.
(iii)
The molecular formula of the compound is CH3NHCH(CH3)2. The structure of the compound is as follows:
The parent chain contains three carbon atoms. A methyl group is attached to a nitrogen atom. In the case of secondary and tertiary amines, use locant N to designate a substituent attached to a nitrogen atom. The structure with numbering is as follows:
Hence, the IUPAC name of the compound is N−methylpropan-2-amine and the amine is secondary because two alkyl groups are attached to a nitrogen atom.
(iv)
The molecular formula of the compound is (CH3)3CNH2. The structure of the compound is as follows:
The parent chain contains three carbon atoms and a methyl group. The structure with numbering is as follows:
The IUPAC name of the compound is 2-methylpropan-2-amine and the amine is primary because only one alkyl group is attached to the nitrogen atom.
(v)
The molecular formula of the compound is C6H5NHCH3. The structure is as follows:
When the benzene ring contains a -NH2 group then it is known as benzamine. The methyl group is attached to the nitrogen atom. Hence, the IUPAC name of the compound is N−Methylbenzamine and the amine is secondary because two alkyl groups are attached to a nitrogen atom.
(vi)
The molecular formula of the compound is (CH3CH2)2NCH3. The structure is as follows:
The parent chain contains two carbon atoms, ethyl, and a methyl group is attached to the nitrogen atom. The compound with a numbering system is as follows:
The IUPAC name of the compound is N-Ethyl-N-methylethanamine and the amine is tertiary because three alkyl groups are attached to a nitrogen atom.
(vii)
The molecular formula of the compound is m–BrC6H4NH2. The structure is as follows:
The NH2 group gets a higher priority than Br. Hence, the IUPAC name of the compound is 3-bromobenzamine and the amine is primary because only one alkyl group is attached to the nitrogen atom.