Carboxylic Acids Esters, Amines and Amides

Carboxylic Acids Esters, Amines and Amides

Carboxylic Acids Esters, Amines and Amides Amines Reactions of Amines Amides Reactions of Amides 1 Amines Organic compounds of nitrogen N Classified as primary, secondary, tertiary CH3 CH3

CH3NH2 CH3NH CH3N CH3 1 2 3 2 Naming Amines IUPAC aminoalkane CH3CH2NH2

aminoethane (ethylamine) Common alkylamine CH3NH CH3 N-methylaminomethane (dimethylamine) NH2 NH CH3 NH2 |

CH3CHCH3 2-aminopropane (isopropylamine) Aniline N-methylaniline 3 Learning Check AM1 Give the common name and classify and give the IUPAC name: A. CH3NHCH2CH3 CH3

| B. CH3CH2NCH3 4 Solution AM1 A. CH3NHCH2CH3 ethylmethylamine, 2, N-methylaminoethane CH3 | B. CH3CH2NCH3 ethyldimethylamine, 3, N,N-dimethylaminoethane 5

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 6

Alkaloids Physiologically active nitrogen-containing compounds Obtained from plants Used as anesthetics, antidepressants, and stimulants Many are addictive 7 Nicotine CH3 N

Nicotine, leaves of tobacco plant 8 Caffeine O CH3 O CH3 N N N

N CH3 Caffeine, coffee beans and tea 9 Procaine CH3CH2 O N

CH2CH2 O C NH2 CH3CH2 Procaine (novocaine), painkiller 10 Leaning Check AM2 Write a structural formula for A. 2-aminopentane

B. 1,3-diaminocyclohexane 11 Solution AM2 A. B. 1-aminopentane CH3CH2CH2CH2CH2-NH2

1,3-diaminocyclohexane NH 2 NH2 12 Amides Derivatives of carboxylic acids where an amino (-NH2) group replaces the OH group. O O

CH3 COH CH3 CNH2 carboxylic acid amide acetic acid acetamide 13

Naming Amides Alkanamide O HCNH2 from acid name methanamide (IUPAC) formamide (common) O CH3CH2CNH2

propanamide (IUPAC) propionamide(common) 14 Naming Amides with N-Groups O CH3CNHCH3 N-methylethanamide (IUPAC) N-methylacetamide (common) O

CH3CH2CN(CH3)2 N,N-dimethylpropanamide N,N-dimethylpropionamide 15 Aromatic Amides O O C NH2 C NHCH3

Benzamide N -methylbenzamide 16 Learning Check AM3 Name the following amides: O A. CH3CH2CH2CNH2 O

B. CH3CN(CH2CH3)2 17 Solution AM3 O A. CH3CH2CH2CNH2 butanamide; butryamide (common) O

B. CH3CN(CH2CH3)2 N,N-diethylethanamide; N,N-diethylacetamide 18 Learning Check AM4 Draw the structures of A. Pentanamide B. N-methylbutanamide 19

Solution AM4 A. Pentanamide O CH3CH2CH2CH2CNH2 B. N-methylbutanamide O CH3CH2CH2CNHCH3 20 Reactions of Amides

Amides undergo acid hydrolysis base hydrolysis carboxylic acid ammonium salt salt of carboxylic acid and an amine or ammonia 21 Reactions of Amides

acid hydrolysis O O HCl + H2O CH3COH + NH4+Cl CH3CNH2 NaOH

O CH3CO Na+ + NH3 base hydrolysis 22 Learning Check AM5 Write the products of the hydrolysis of N- ethylpropanamide with NaOH. 23

Solution AM5 Hydrolysis of N-ethylpropanamide with NaOH gives the following products. O CH3CH2CO Na+ + CH3CH2NH2 24

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