Chapter 19 Amines

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Chapter 19 Amines
NOTE We are skipping sections 7,8,11B-C,14,16,17
YEAH!!!

• Properties
• 1. basicity

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a. inductive effects
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b. aromaticity
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c. hybridization
d. amides
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sp3 hybridization at N pyramidal
2. structures
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WHY???
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B. Nomenclature 1. common - name the alkyl
portions and follow this by the suffix amine,
i.e.
2. IUPAC - drope in alkane name add amine
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3. naming as a substituent - amino
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4. aromatic amines, heterocycles
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C. Spectroscopy 1. IR - 1 amines - 2 peaks
2 amines - 1 peak 2. 1H NMR - broad peak
for NH ?1-4 ppm - exchanges with D2O D. Uses
3200 - 3500 cm-1
Haber-Bosch process makes 30 billion tons per
year fertilizer
oder from decaying flesh -produced by bacteria
You guessed it!!
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Alkaloid -any nitrogen containing compound
extracted from plants.
morphine
opium alkaloids
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tropane alkaloids
indole alkaloids
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bark of the cinchona tree treatment for malaria
one of the first molecules to be synthesized
Sildenafil (citric acid salt Viagra)
Patent to Pfizer 192 1993
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Bitrex - most bitter substance known
completely nontoxic thumb sucking
fingernail biting
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D. Reactions of amines 1. formation of imines -
see Chapter 18.16
Note
know reaction mechanism!! (acid and base cat.)
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2. nucleophillic substitution
But
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3. elimination reactions
4. Aromatic substitution - NH2 is a very strong
activating group -NH3 is a very strong
deactivating group
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To get around this we normally use an amide
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5. the Sandmeyer reactions
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E. Preparation of amines 1. reduction of -NO2
and -CN compounds
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prep. of diazo compd.
nitration
Sandmeyer rxns.
2. reductive animation
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??
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3. acylation - reduction
Also
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4. Gabriel synthesis - prevents over-alkylation
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6. reduction of azides
7. Hofmann rearrangement
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8. Curtius rearrangement
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What happens using an amine, RNH2???
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F. Summary 1. Basicity of amines a. inductive
effects b. resonance/ aromaticity c.
hybridization 2. Pyramidalization of amines 3.
Nomenclature 4. Spectroscopy 5. Aromatic
substitution a. using amides (acetamides) b.
Sandmeyer reactions 6. Reduction reactions a.
NO2 and CN compounds b. reductive
animation c. acylation - reduction 7. Gabriel
synthesis
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8. Reduction of azides 9. Hofmann rearrangement -
mech. 10. Curtius rearrangement - mech.
THE END??????