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Carboxylic Acids Esters, Amines and AmidesAminesReactions of AminesAmidesReactions of Amides
AminesOrganic compounds of nitrogen NClassified as primary, secondary, tertiary CH3 CH3 CH3NH2 CH3NH CH3N CH3
1 2 3
Naming AminesIUPAC aminoalkane Common alkylamineCH3CH2NH2 CH3NH CH3aminoethane N-methylaminomethane(ethylamine) (dimethylamine)
NH2 |CH3CHCH32-aminopropane AnilineN-methylaniline(isopropylamine)
Learning Check AM1Give the common name and classify:
A. CH3NHCH2CH3 CH3 |B.CH3CH2NCH3
Solution AM1A.CH3NHCH2CH3ethylmethylamine, 2 CH3 |CH3CH2NCH3ethyldimethylamine, 3
Reactions of AminesAct as weak bases in waterCH3NH2 + H2O CH3NH3+ + OH methylammonium hydroxide
Neutralization with acid gives ammonium saltCH3NH2 + HClCH3NH3+ Clmethylammonium chloride
AlkaloidsPhysiologically active nitrogen-containing compoundsObtained from plantsUsed as anesthetics, antidepressants, and stimulantsMany are addictive
Nicotine
Caffeine
Procaine
Leaning Check AM2Write a structural formula for
2-aminopentane
B. 1,3-diaminocyclohexane
Solution AM2A. 1-aminopentane CH3CH2CH2CH2CH2-NH2
B. 1,3-diaminocyclohexane
AmidesDerivatives of carboxylic acids where an amino (-NH2) group replaces the OH group. O O CH3 COH CH3 CNH2 carboxylic acid amide acetic acidacetamide
Naming AmidesAlkanamidefrom acid name O methanamide (IUPAC)HCNH2formamide (common)
O propanamide (IUPAC)CH3CH2CNH2propionamide(common)
Naming Amides with N-Groups O CH3CNHCH3N-methylethanamide (IUPAC)N-methylacetamide (common) O CH3CH2CN(CH3)2N,N-dimethylpropanamideN,N-dimethylpropionamide
Aromatic Amides
Learning Check AM3Name the following amides: O A. CH3CH2CH2CNH2 O B. CH3CN(CH2CH3)2
Solution AM3 O A. CH3CH2CH2CNH2butanamide; butryamide (common)
O B.CH3CN(CH2CH3)2N,N-diethylethanamide;N,N-diethylacetamide
Learning Check AM4Draw the structures of A.PentanamideB.N-methylbutyramide
Solution AM4A.Pentanamide O CH3CH2CH2CH2CNH2
B.N-methylbutyramide O CH3CH2CH2CNHCH3
Reactions of AmidesAmides undergo
acid hydrolysis base hydrolysis
carboxylic acid salt of carboxylic acidammonium salt and an amine or ammonia
Reactions of Amides acid hydrolysis O O HCl + H2O CH3COH + NH4+Cl CH3CNH2 O NaOH CH3CO Na+ + NH3 base hydrolysis
Learning Check AM5Write the products of the hydrolysis of N- ethylpropanamide with NaOH.
Solution AM5Hydrolysis of N-ethylpropanamide with NaOH gives the following products.
O CH3CH2CO Na+ + CH3CH2NH2