PROBLEMS CH 18

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Learning CheckGive the common and IUPAC names, and classify each as primary,secondary, or tertiary.

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SolutionA.

STEP 1 Name the longest carbon chain bonded to the NSTEP 1 atoms as alkanamines by replacing e of theSTEP 1 alkane name with amine.

STEP 2 Number the carbon chain to show the position ofSTEP 2 the amine group and any substituents.

CH3—CH2 —CH2—NH2

Propylamine (common), 1°

1-Propanamine (IUPAC)

3 2 1

Propanamine

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Solution (continued)

ethanamine

B.

STEP 1 Name the longest carbon chain bonded to the NSTEP 1 atoms as alkanamines by replacing e of theSTEP 1 alkane name with amine.

STEP 2 Number the carbon chain to show the position ofSTEP 2 the amine group and any substituents.

5

Solution (continued)B.

STEP 3 In a secondary or tertiary amine, use the prefixSTEP 3 N- to name groups attached to the N atom.

Ethyldimethylamine (common),

N,N-Dimethylethanamine (IUPAC), 3°

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Learning CheckDraw the condensed structural formula for each of the following:

A. 2-pentanamine

B. N-methyl-1-butanamine

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Solution

CH3—CH2—CH2—CH2—NH—CH3

Draw the condensed structural formula for each ofthe following:

A. 2-pentanamine

B. N-methyl-1-butanamine

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Learning Check Give the common and IUPAC names for each of the following:

A.

B.

C.

NH2

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Solution

Ethylmethylamine(common); N-methylethanamine

A.

B.

C.

NH2

Butylethylmethylamine (common);N-ethyl-N-methyl-1-butanamine

Aniline

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Classification of Amines Amines are classified as primary, secondary, or tertiary.

In a primary (1) amine, one carbon group is bonded to the nitrogen atom.

A secondary (2) amine has two carbon groups.

A tertiary (3) amine has three carbon groups.

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Learning Check

Consider the following compounds:1) CH3—CH2—CH2—NH2

2) CH3—CH2—NH—CH3

3) CH3—CH2—CH2—CH3

A. Which compound has the highest boiling point?

B. Which compound(s) is/are soluble in water?

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Solution

Consider the following compounds:1) CH3—CH2—CH2—NH2

2) CH3—CH2—NH—CH3

3) CH3—CH2—CH2—CH3

A. Which compound has the highest boiling point?1) CH3—CH2—CH2—NH2

B. Which compound(s) is/are soluble in water?1) CH3—CH2—CH2—NH2

2) CH3—CH2—NH—CH3

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Learning Check

Identify the following heterocyclic amines: A. B. C.

N

H

N

H

N

H

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Solution

Identify the following heterocyclic amines: A. B. C.

Piperidine Pyrrolidine Pyrrole

N

H

N

H

N

H

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Learning Check

Identify the heterocyclic amine in serotonin.

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Solution

The heterocyclic amine in serotonin is pyrrole.

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Write the IUPAC name for

STEP 1 Determine the alkane name of the carbon chain in the carboxyl portion and replace e with amide.

butanamide STEP 2 Name each substituent on the N atom using the prefix N- and the alkyl name.

N-ethylbutanamide

IUPAC Names of Amides

N-Methylethanamide (IUPAC)N-Methylacetamide (common)

N-Ethylpropanamide (IUPAC)N-Ethylpropionamide (common)

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CH3—C H2—C—N—CH2—CH3

O║

H—

Examples of IUPAC and Common Names

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CH3—CH2—CH2—CH2—C—N—CH2—CH3

O║

CH2—CH3│

Learning Check

Write the IUPAC name for the following:

STEP 1 Determine the alkane name of the carbon chain in the carboxyl portion and replace e with amide.

pentanamide STEP 2 Name each substituent on the N atom using the prefix N- and the alkyl name.

N,N-diethylpentanamide

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Solution

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Learning Check

Draw the condensed structural formulas of the following amides.

A. pentanamide

B. N-methylbutyramide

Draw the condensed structural formulas of the following amides.

A. pentanamide

B. N-methylbutyramide

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Solution

Give the common and IUPAC names for the followingamides, and classify them as primary, secondary, or tertiary.

A.

B.

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Learning Check

Give the common and IUPAC names for the followingamides, and classify them as primary, secondary, or tertiary.

A.

B.

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Butryamide (common)butanamide (IUPAC)primary (1)

N-ethyl-N-methylethanamide (IUPAC), tertiary

N-Ethyl-N-methylacetamide (common) (3)

Solution