amines and amides

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1 Carboxylic Acids Esters, Amines and Amides Amines Reactions of Amines Amides Reactions of Amides

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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