Amines and Amides Amines Reactions of Amines Amides

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Presentation transcript:

Amines and Amides Amines Reactions of Amines Amides Reactions of Amides

Amines Organic compounds of nitrogen N Classified as primary, secondary, tertiary CH3 CH3   CH3—NH2 CH3—NH CH3—N — CH3 1° 2° 3°

Naming Amines IUPAC aminoalkane Common alkylamine CH3CH2NH2 CH3—NH —CH3 aminoethane N-methylaminomethane (ethylamine) (dimethylamine) NH2 | CH3CHCH3 2-aminopropane Aniline N-methylaniline (isopropylamine)

Practice Naming Give the common name and classify as primary, secondary or tertiary: CH3NHCH2CH3 CH3 | B. CH3CH2NCH3

Solution A. CH3NHCH2CH3 N-methylaminoethane (ethylmethylamine), 2° CH3 | CH3CH2NCH3 N,N-dimethylaminoethane (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

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

Nicotine

Caffeine

Procaine

Practice Write a structural formula for 1-aminopentane B. 1,3-diaminocyclohexane

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

More naming practice Draw: N-methyl-N-propyl-2-aminobutane

Solution

Properties of Amines When organisms decompose, large and complex molecules such as proteins are broken down into simpler amines. Amines often have an unpleasant odour, such as rotting fish. Putrescine (1,4-diaminobutane) and Cadavarine (1,5-diaminopentane) are amines produced by bacteria when animal tissue decomposes.

Properties cntd Amines have higher melting and boiling points than comparable hydrocarbons as they are more polar. Amines with 1-5 carbons are soluble in water. When N-H bonds are present (primary or secondary amines), hydrogen bonding can occur with water. The N-H bond is not as polar as the O-H bond in alcohols.

Preparing Amines Preparing a Primary Amine (ammonia reacts with an alkyl halide)

Secondary Amines Preparing a Secondary Amine (primary amine reacts with alkyl halide)

Tertiary Amines Preparing a Tertiary Amine (secondary amine reacts with alkyl halide)

Amides Derivatives of carboxylic acids where an amino (-NH2) group replaces the –OH group. (CON) O O   CH3 — C—OH CH3 — C—NH2 carboxylic acid amide acetic acid ethanamide

Naming Amides Alkanamide from acid name O  methanamide (IUPAC) HC–NH2 formamide (common)  propanamide (IUPAC) CH3CH2C–NH2 propionamide(common)

Naming Amides with N-Groups  CH3C–NHCH3 N-methylethanamide (IUPAC) N-methylacetamide (common) CH3CH2C–N(CH3)2 N,N-dimethylpropanamide N,N-dimethylpropionamide

Aromatic Amides

Practice Name the following amides: O  A. CH3CH2CH2C–NH2 B. CH3C–N(CH2CH3)2

Solution  A. CH3CH2CH2C–NH2 butanamide; butryamide (common) B. CH3C–N(CH2CH3)2 N,N-diethylethanamide; N,N-diethylacetamide

Practice Draw the structures of A. Pentanamide B. N-methylbutanamide

Solution A. Pentanamide O  CH3CH2CH2CH2C–NH2 B. N-methylbutanamide CH3CH2CH2C–NHCH3

Preparing Amides Carboxylic Acid + Ammonia Carboxylic Acid with Primary or Secondary Amine

Reactions of Amides Amides undergo acid hydrolysis base hydrolysis carboxylic acid salt of carboxylic acid ammonium 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

Practice Write the products of the hydrolysis of N- ethylpropanamide with NaOH.

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

Properties of Amides Amides are weak bases and generally insoluble in water. Smaller amides are slightly soluble in water due to hydrogen bonding with NH group of amide and OH group of water. Amides whose N atoms are bonding to two H atoms have higher melting and boiling points than those with more alkyl groups attached due to more hydrogen bonding. Amide functional groups (CON) are an important linkage in proteins.