carboxylic acids esters, amines and amides
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Carboxylic Acids Esters, Amines and Amides
Amines
Reactions of Amines
Amides
Reactions of Amides
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Amines
• Organic compounds of nitrogen N• Classified as primary, secondary, tertiary
CH3 CH3
CH3—NH2 CH3—NH CH3—N — CH3
1° 2° 3°
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Naming Amines
IUPAC aminoalkane Common alkylamine
CH3CH2NH2 CH3—NH —CH3
aminoethane N-methylaminomethane(ethylamine) (dimethylamine)
NH2
|
CH3CHCH3
2-aminopropane Aniline N-methylaniline(isopropylamine)
NH2 NH CH3
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Learning Check AM1
Give the common name and classify:
A. CH3NHCH2CH3
CH3
|
B. CH3CH2NCH3
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Solution AM1
A. CH3NHCH2CH3
ethylmethylamine, 2°
CH3
|B. CH3CH2NCH3
ethyldimethylamine, 3°
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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
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Nicotine
N
CH3
Nicotine, leaves of tobacco plant
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Caffeine
N
N N
NCH3
O
O CH3
CH3
Caffeine, coffee beans and tea
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Procaine
NH2N
CH3CH2
CH3CH2
CH2CH2 O C
O
Procaine (novocaine), painkiller
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Leaning Check AM2
Write a structural formula for
A. 2-aminopentane
B. 1,3-diaminocyclohexane
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Solution AM2
A. 1-aminopentane
CH3CH2CH2CH2CH2-NH2
B. 1,3-diaminocyclohexaneNH2
NH2
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Amides
Derivatives of carboxylic acids where an amino (-NH2) group replaces the –OH group.
O O
CH3 — C—OH CH3 — C—NH2
carboxylic acid amide
acetic acid acetamide
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Naming Amides
Alkanamide from acid name
O
methanamide (IUPAC)
HC–NH2 formamide (common)
O propanamide (IUPAC)
CH3CH2C–NH2 propionamide(common)
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Naming Amides with N-Groups
O
CH3C–NHCH3 N-methylethanamide (IUPAC)
N-methylacetamide (common) O
CH3CH2C–N(CH3)2
N,N-dimethylpropanamide
N,N-dimethylpropionamide
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Aromatic Amides
C
O
NH2
Benzamide
C
O
NHCH3
N methylbenzamide -
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Learning Check AM3
Name the following amides: O
A. CH3CH2CH2C–NH2
O
B. CH3C–N(CH2CH3)2
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Solution AM3
O
A. CH3CH2CH2C–NH2
butanamide; butryamide (common)
O
B. CH3C–N(CH2CH3)2
N,N-diethylethanamide;
N,N-diethylacetamide
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Learning Check AM4
Draw the structures of
A. Pentanamide
B. N-methylbutyramide
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Solution AM4
A. Pentanamide O
CH3CH2CH2CH2C–NH2
B. N-methylbutyramide O
CH3CH2CH2C–NHCH3
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Reactions of Amides
Amides undergo
acid hydrolysis base hydrolysis
carboxylic acid salt of carboxylic acid
ammonium salt and an amine or ammonia
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Reactions of Amides
acid hydrolysis O
O HCl + H2O CH3COH + NH4+Cl–
CH3CNH2 O
NaOH
CH3CO– Na+ + NH3
base hydrolysis
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Learning Check AM5
Write the products of the hydrolysis of
N- ethylpropanamide with NaOH.
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Solution AM5
Hydrolysis of N-ethylpropanamide with NaOH gives the following products.
O
CH3CH2CO– Na+ + CH3CH2NH2
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