Amines and Amides
Amines and Amides
Amines and 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
3
Common alkylamine
CH3NH CH3 N-methylaminomethane (dimethylamine)
NH 2
NH CH3
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
Caffeine
O CH3 O N N CH3 N N
Procaine
CH3CH2 N CH3CH2 Procaine (novocaine), painkiller O CH2CH2 O C NH2
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11
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
Naming Amides
Alkanamide O HCNH2
O CH3CH2CNH2
Aromatic Amides
O C NH2 O C NHCH3
Benzamide
N -methylbenzamide
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B.
Solution AM3
O
A.
B.
CH3CN(CH2CH3)2
N,N-diethylethanamide; N,N-diethylacetamide
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19
Solution AM4
A. Pentanamide
O
CH3CH2CH2CH2CNH2
B. N-methylbutyramide O
CH3CH2CH2CNHCH3
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Reactions of Amides
Amides undergo
acid hydrolysis base hydrolysis
Reactions of Amides
acid hydrolysis
O
HCl + H2O
CH3COH + NH4+Cl O
CH3CNH2 NaOH
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Solution AM5
Hydrolysis of N-ethylpropanamide with NaOH gives the following products.
O
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