Karen C. Timberlake Chapter - PowerPoint Presentation

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Karen C. Timberlake

Chapter 18Amines and Amides

Lecture Presentation

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Chapter 18 Amines and AmidesEnvironmental 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.

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Chapter 18 ReadinessCore

Chemistry SkillsWriting Equations for Reactions of Acids and Bases (10.6)Naming and Drawing Alkanes (11.2)

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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°).

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AminesAmines

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.

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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 —NH

2

group and any other substituents.

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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.

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Guide to IUPAC Naming of Amines

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Study CheckGive the IUPAC name for the following amine:

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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

.

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SolutionGive the IUPAC name for the following amine:

STEP 2

Number the carbon chain to show the

position of the amine group and other substituents

.

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SolutionGive 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

.

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Common Names of AminesCommon 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

Dimethyl

amine

Ethyldimethyl

amine

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Naming Compounds, Two Functional GroupsWhen 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.

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Guide to Naming Compounds with Two Functional Groups

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

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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.

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SolutionGive 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.

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Aromatic AminesThe 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.

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Classification of AminesAmines 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°

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Study CheckGive the common name for each amine and classify it as primary, secondary, or tertiary.

A. CH3—CH2—CH2—NH2

B.

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SolutionGive the common name for each amine and classify it as primary, secondary, or tertiary.

A. CH3—CH2—CH2—NH2 propylamine

, 1°

B.

ethyldimethylamine

,

3

°

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Study CheckGive the common name of each amine compound.

A. B.

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SolutionGive the common name of each amine compound.

A. diethylmethylamine

B. N-

ethylaniline

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Line-Angle Structures of AminesThe skeletal structures show the shapes of amine molecules with one or more alkyl groups bonded to the nitrogen atom.