Chapter 18 Amines and Amides Lecture Presentation Chapter 18 Amines and Amides Karen C. Timberlake

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.

Chapter 18 Readiness Core Chemistry Skills Writing Equations for Reactions of Acids and Bases (10.6) Naming and Drawing Alkanes (11.2)

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°).

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.

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.

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.

Guide to IUPAC Naming of Amines

Study Check Give the IUPAC name for the following amine:

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.

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.

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.

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 Dimethylamine Ethyldimethylamine

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.

Guide to Naming Compounds with Two Functional Groups

Study Check Give the IUPAC name for the following compound, which is used in the production of methadone:

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.

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.

N-methylaniline aniline 3-chloroaniline Aromatic Amines The amine of benzene is named aniline by IUPAC. Alkyl groups on the N use the prefix N with the alkyl name. 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.

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. 1° 2° 3°

Study Check Give the common name for each amine and classify it as primary, secondary, or tertiary. A. CH3—CH2—CH2—NH2 B.

Solution Give the common name for each amine and classify it as primary, secondary, or tertiary. A. CH3—CH2—CH2—NH2 propylamine, 1° B. ethyldimethylamine, 3°

Study Check Give the common name of each amine compound. A. B.

Solution Give the common name of each amine compound. A. diethylmethylamine B. N-ethylaniline

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.