Carboxylic Acids Esters, Amines and Amides

Amines Reactions of Amines Amides Reactions of Amides

Amines
Organic compounds of nitrogen N Classified as primary, secondary, tertiary CH3 CH3 CH3NH2 CH3NH CH3N CH3
1 2 3

Naming Amines
IUPAC aminoalkane
CH3CH2NH2 aminoethane (ethylamine) NH2 | CH3CHCH3 2-aminopropane (isopropylamine) Aniline N-methylaniline
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Common alkylamine
CH3NH CH3 N-methylaminomethane (dimethylamine)

NH 2

NH CH3

Learning Check AM1

Give the common name and classify:
A. CH3NHCH2CH3 CH3 | B. CH3CH2NCH3

Solution AM1
A. CH3NHCH2CH3 ethylmethylamine, 2 CH3 | B. CH3CH2NCH3 ethyldimethylamine, 3

Reactions of Amines
Act as weak bases in water CH3NH2 + H2O CH3NH3+ + OH methylammonium hydroxide
Neutralization with acid gives ammonium salt CH3NH2 + HCl CH3NH3+ Cl methylammonium chloride
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Alkaloids
Physiologically active nitrogen-containing compounds Obtained from plants Used as anesthetics, antidepressants, and stimulants Many are addictive

Nicotine

CH3 N

Nicotine, leaves of tobacco plant

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Caffeine
O CH3 O N N CH3 N N

CH3 Caf f e in e , cof f e e b e an s an d t e a

Procaine
CH3CH2 N CH3CH2 Procaine (novocaine), painkiller O CH2CH2 O C NH2

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Leaning Check AM2

Write a structural formula for
A. B. 2-aminopentane 1,3-diaminocyclohexane

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Solution AM2
A. 1-aminopentane CH3CH2CH2CH2CH2-NH2 1,3-diaminocyclohexane
NH2

B.

NH2

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Amides
Derivatives of carboxylic acids where an amino (-NH2) group replaces the OH group. O O

CH3 COH carboxylic acid acetic acid

CH3 CNH2 amide acetamide

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Naming Amides
Alkanamide O HCNH2
O CH3CH2CNH2

from acid name

methanamide (IUPAC) formamide (common)

propanamide (IUPAC) propionamide(common)

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Naming Amides with N-Groups

O CH3CNHCH3

N-methylethanamide (IUPAC) N-methylacetamide (common)

O CH3CH2CN(CH3)2 N,N-dimethylpropanamide N,N-dimethylpropionamide

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Aromatic Amides
O C NH2 O C NHCH3

Benzamide

N -methylbenzamide
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Learning Check AM3

Name the following amides: O A. CH3CH2CH2CNH2
O CH3CN(CH2CH3)2
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B.

Solution AM3
O

A.

CH3CH2CH2CNH2 butanamide; butryamide (common) O

B.

CH3CN(CH2CH3)2
N,N-diethylethanamide; N,N-diethylacetamide
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Learning Check AM4

Draw the structures of A. Pentanamide B. N-methylbutyramide

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Solution AM4
A. Pentanamide
O

CH3CH2CH2CH2CNH2
B. N-methylbutyramide O

CH3CH2CH2CNHCH3

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Reactions of Amides
Amides undergo
acid hydrolysis base hydrolysis

carboxylic acid ammonium salt

salt of carboxylic acid and an amine or ammonia

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Reactions of Amides
acid hydrolysis
O

HCl + H2O

CH3COH + NH4+Cl O

CH3CNH2 NaOH

CH3CO Na+ + NH3 base hydrolysis

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Learning Check AM5

Write the products of the hydrolysis of N- ethylpropanamide with NaOH.

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Solution AM5
Hydrolysis of N-ethylpropanamide with NaOH gives the following products.
O

CH3CH2CO Na+ + CH3CH2NH2

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