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Lecture Presentation
Chapter 18
Amines and
Amides
Karen C. Timberlake
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Chapter 18 Amines and Amides
Environmental health
practitioners (EHPs) monitor
environmental pollution to
protect the health of the public.
By using specialized equipment,
EHPs measure
• pollution levels in soil, air, and
water.
• noise and radiation levels.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Chapter 18 Readiness
Core Chemistry Skills
• Writing Equations for Reactions of Acids and Bases
(10.6)
• Naming and Drawing Alkanes (11.2)
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
18.1 Amines
Indigo used in blue dyes can be obtained from tropical plants
such as Indigofera tinctoria.
Learning Goal Name amines using IUPAC and common
names; draw the condensed or line-angle structural formulas
when given the names. Classify amines as primary (1°),
secondary (2°), or tertiary (3°).
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Amines
Amines
• are derivatives of ammonia, NH3, in which one or
more hydrogen atoms are replaced with alkyl or
aromatic groups.
• contain N attached to one or more alkyl or aromatic
groups.
CH3 —CH2—CH2—N—CH3
CH3
H N H
H—N—CH2—CH3
CH3
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Naming Amines, IUPAC
In the IUPAC names for amines, the e in the corresponding alkane name is
replaced with amine.
Amines with a chain of three or more carbon atoms are numbered to show
the position of the —NH2 group and any other substituents.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Naming Amines, IUPAC
• If there is an alkyl group attached to the nitrogen atom,
the prefix N and the alkyl name are placed in front of the
amine name.
• If there are two alkyl groups bonded to the N atom, the
prefix N is used for each, and they are listed
alphabetically.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Guide to IUPAC Naming of Amines
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Study Check
Give the IUPAC name for the following amine:
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Solution
Give the IUPAC name for the following amine:
STEP 1 Name the longest carbon chain bonded
to the N atom by replacing the e of its
alkane name with amine.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Solution
Give the IUPAC name for the following amine:
STEP 2 Number the carbon chain to show the
position of the amine group and other
substituents.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Solution
Give the IUPAC name for the following amine:
STEP 3 Any alkyl group attached to the nitrogen
atom is indicated by the prefix N and the
alkyl name, which is placed in front of the
amine name.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Common Names of Amines
Common names are often used when alkyl groups are not
branched.
• List the names of the alkyl groups bonded to the N atom in
alphabetical order in front of amine.
• Use prefixes di and tri to identify duplicate alkyl substituents.
Ethylamine
CH3 —CH2—NH2
Dimethylamine
CH3 —NH—CH3
CH3 —N—CH2—CH3
Ethyldimethylamine
CH3
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Naming Compounds, Two Functional
Groups
When a compound contains more than one functional group, IUPAC
rules for nomenclature state that an oxygen-containing group will
take priority over an —NH2 group, and the —NH2 group is named as
the substituent, amino.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Guide to Naming Compounds with Two
Functional Groups
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Study Check
Give the IUPAC name for the following compound, which
is used in the production of methadone:
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Solution
Give the IUPAC name for the following compound, which
is used in the production of methadone:
STEP 1 Identify the functional group with the highest
priority and use the longest carbon chain to
give the compound name.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Solution
Give the IUPAC name for the following compound, which
is used in the production of methadone:
STEP 2 Number the carbon chain, and give the
position and name of the main group and
the substituent group on the carbon chain.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Aromatic Amines
The amine of benzene is named aniline by IUPAC.
• Alkyl groups on the N use the prefix N with the alkyl name.
HN CH3
H—N—CH3
NH2
Cl
N-methylaniline
aniline
3-chloroaniline
• Aniline is used to make many dyes, which give color to
wool, cotton, and silk fibers as well as blue jeans.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Classification of Amines
Amines are classified as primary, secondary, or tertiary.
• A primary (1°) amine has one carbon group bonded to the
nitrogen atom.
• A secondary (2°) amine has two carbon groups bonded to the
nitrogen atom.
• A tertiary (3°) amine has three carbon groups bonded to the
nitrogen atom.
H N H
H—N—CH3
CH3 —N—CH3
CH3
CH3
CH3
1°
2°
3°
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Study Check
Give the common name for each amine and classify it as
primary, secondary, or tertiary.
A. CH3—CH2—CH2—NH2
CH3
B. CH3 —CH2—N—CH3
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Solution
Give the common name for each amine and classify it as
primary, secondary, or tertiary.
A. CH3—CH2—CH2—NH2
propylamine, 1°
CH3
B. CH3 —CH2—N—CH3
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
ethyldimethylamine, 3°
© 2016 Pearson Education, Inc.
Study Check
Give the common name of each amine compound.
CH3
A. CH3 —CH2—N—CH2—CH3
B. H—N—CH2—CH3
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Solution
Give the common name of each amine compound.
CH3
A. CH3 —CH2—N—CH2—CH3
diethylmethylamine
B. H—N—CH2—CH3
N-ethylaniline
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.
Line-Angle Structures of Amines
The skeletal structures show the shapes of amine molecules
with one or more alkyl groups bonded to the nitrogen atom.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C. Timberlake
© 2016 Pearson Education, Inc.