Carboxylic Acids Esters,

Amines and Amides

Amines
Reactions of Amines
Amides
Reactions of Amides

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 Amines
• Organic compounds of nitrogen N
• Classified as primary, secondary, tertiary
CH3 CH3
 
CH3—NH2 CH3—NH CH3—N — CH3

1° 2° 3°

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 Naming Amines
IUPAC aminoalkane Common alkylamine
CH3CH2NH2 CH3—NH —CH3
aminoethane N-methylaminomethane
(ethylamine) NH (dimethylamine)
2 NH CH3
NH2
|
CH3CHCH3
2-aminopropane Aniline N-methylaniline
(isopropylamine) 3
 Learning Check AM1
Give the common name and classify:

A. CH3NHCH2CH3
CH3
|
B. CH3CH2NCH3

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 Solution AM1
A. CH3NHCH2CH3
ethylmethylamine, 2°

CH3
|
• CH3CH2NCH3
ethyldimethylamine, 3°

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 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

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 Nicotine

CH3
N

Nicotine, leaves of tobacco plant

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 Caffeine
O CH3
CH3 N
N

O N N
CH3
Caffeine, coffee beans and tea

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 Procaine
CH3CH2 O
N CH2CH2 O C NH2
CH3CH2

Procaine (novocaine), painkiller

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 Leaning Check AM2
Write a structural formula for

C. 2-aminopentane

B. 1,3-diaminocyclohexane

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 Solution AM2
A. 1-aminopentane
CH3CH2CH2CH2CH2-NH2

B. 1,3-diaminocyclohexane
NH2

NH2
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 Amides
Derivatives of carboxylic acids where an
amino (-NH2) group replaces the –OH
group.
O O
|| ||
CH3 — C—OH CH3 — C—NH2
carboxylic acid amide
acetic acid acetamide
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 Naming Amides
Alkanamide from acid name
O
|| methanamide (IUPAC)
HC–NH2 formamide (common)

O
|| propanamide (IUPAC)
CH3CH2C–NH2 propionamide(common)
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 Naming Amides with N-Groups
O
||
CH3C–NHCH3 N-methylethanamide (IUPAC)
N-methylacetamide (common)
O
||
CH3CH2C–N(CH3)2
N,N-dimethylpropanamide
N,N-dimethylpropionamide 15
 Aromatic Amides

O O
C NH2 C NHCH 3

Benzamide N -methylbenzamide
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 Learning Check AM3
Name the following amides:
O
||
A. CH3CH2CH2C–NH2

O
||
B. CH3C–N(CH2CH3)2

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 Solution AM3
O
||
A. CH3CH2CH2C–NH2
butanamide; butryamide (common)
O
||
B. CH3C–N(CH2CH3)2
N,N-diethylethanamide;
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N,N-diethylacetamide
 Learning Check AM4
Draw the structures of
A. Pentanamide
B. N-methylbutyramide

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 Solution AM4

A. Pentanamide
O
||
CH3CH2CH2CH2C–NH2

B. N-methylbutyramide
O
||
CH3CH2CH2C–NHCH3 20
 Reactions of Amides
Amides undergo

acid hydrolysis base hydrolysis

carboxylic acid salt of carboxylic acid

ammonium salt and an amine
or ammonia
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 Reactions of Amides
acid hydrolysis O
||
O HCl + H2O CH3COH + NH4+Cl–
||

CH3CNH2 O
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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