Amines - University of Al-Qadisiyahqu.edu.iq/ph/wp-content/uploads/2015/03/Amines.pdf ·...
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AminesAmines
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Physical Properties of Amines
- Amines are moderately polar. For this reason the low formulaweight amines are readily soluble in water due to theformation of hydrogen bonds with water.
- They have higher boiling points than non-polar compounds of thesame molecular weight, because of the formation of intermolecularhydrogen bonds, except for tertiary amines.
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- They have higher boiling points than non-polar compounds of thesame molecular weight, because of the formation of intermolecularhydrogen bonds, except for tertiary amines.
(Intermolecular H bonds)(H bonds with water)
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Physical Properties of Amines
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Basicity of Amines• The lone pair of electrons on nitrogen makes amines
basic and nucleophilic• They react with acids to form acid–base salts and they
react with electrophiles• Amines are stronger bases than alcohols, ethers, or
water
• The lone pair of electrons on nitrogen makes aminesbasic and nucleophilic
• They react with acids to form acid–base salts and theyreact with electrophiles
• Amines are stronger bases than alcohols, ethers, orwater
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Amines as Bases
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High pKa → weaker acid and stronger conjugate base.
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Aliphatic amines are stronger bases than aromatic amines because ofthe resonance in aromatic amines
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Electron-donating groups increase the basicity of amines,Electron-withdrawing groups decrease the basicity of amines
CH3CH2NH2 CH2(Cl)CH2NH2
NH2
CH3
NH2
H
NH2
NO2
>>
is stronger base than
stronger base
CH3CH2NH2 CH2(Cl)CH2NH2
NH2
CH3
NH2
H
NH2
NO2
>>
is stronger base than
stronger base
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amines are stronger bases than amides
• Amides (RCONH2) in general are not proton acceptors exceptin very strong acid
• The C=O group is strongly electron-withdrawing, making theN a very weak base
• Addition of a proton occurs on O but this destroys the doublebond character of C=O as a requirement of stabilization by N
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• Amides (RCONH2) in general are not proton acceptors exceptin very strong acid
• The C=O group is strongly electron-withdrawing, making theN a very weak base
• Addition of a proton occurs on O but this destroys the doublebond character of C=O as a requirement of stabilization by N
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1- Reduction of Nitriles and AmidesSynthesis of Amines
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CH2BrNaCN
CH2C N2 H2, Ni
CH2CH2NH2
benzyl bromide 1-amino-2-phenylethane
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2. Reduction of nitro compounds:
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CH3HNO3,H2SO4
CH3
NO2
+ ortho-
H2,Ni
CH3
NH2
p-toluidine
CH3HNO3,H2SO4
CH3
NO2
+ ortho-
H2,Ni
CH3
NH2
p-toluidine
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3- Ammonolysis of 1o or methyl halides.
R-XNH3 RNH2
R-X R2NHR-X
R3N
R-X
R4N+X-
1o 2o 3o
4o saltR-X must be 1o or CH3
CH3CH2CH2CH2BrNH3
CH3CH2CH2CH2NH2n-butylamine
R-XNH3 RNH2
R-X R2NHR-X
R3N
R-X
R4N+X-
1o 2o 3o
4o saltR-X must be 1o or CH3
CH3CH2CH2CH2BrNH3
CH3CH2CH2CH2NH2n-butylamine
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4. Reductive amination:
OH2, Ni
or NaBH3CNCH NH2+ NH3
OH2, Ni
or NaBH3CNCH NHR+ RNH2
OH2, Ni
or NaBH3CNCH NR2+ R2NH
1o amine
3o amine
2o amine
• Ammonia, primary amines, and secondary amines yieldprimary, secondary, and tertiary amines, respectively
OH2, Ni
or NaBH3CNCH NH2+ NH3
OH2, Ni
or NaBH3CNCH NHR+ RNH2
OH2, Ni
or NaBH3CNCH NR2+ R2NH
1o amine
3o amine
2o amine
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Mechanism of Reductive Amination• Imine is intermediate
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H3CCO
CH3
acetone
NH3, H2/NiCH3CHCH3
NH2
isopropylamine
CCH2CH3
O
propiophenone
+ CH3CH2NH2NaBH3CN
CHCH2CH3
NHCH2CH3
1-(N-ethylamino)-1-phenylpropane
O
cyclohexanone
NH3, H2/Ni NH2
cyclohexylamine
H3CCO
CH3
acetone
NH3, H2/NiCH3CHCH3
NH2
isopropylamine
CCH2CH3
O
propiophenone
+ CH3CH2NH2NaBH3CN
CHCH2CH3
NHCH2CH3
1-(N-ethylamino)-1-phenylpropane
O
cyclohexanone
NH3, H2/Ni NH2
cyclohexylamine
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5. Hofmann degradation of amides
R CNH2
O KOBrR-NH2
Removes one carbon!
2,2-dimethylpropanamide
OBrCH3C
CH3
CH3
NH2
tert-butylamine
CH3CCH3
CH3
CO
NH2
R CNH2
O KOBrR-NH2
Removes one carbon!
2,2-dimethylpropanamide
OBrCH3C
CH3
CH3
NH2
tert-butylamine
CH3CCH3
CH3
CO
NH2
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Reactions of Amines- The lone-pair of electrons on the nitrogen atom dominates thechemistry of the amines and cause them to function as Lewisbases or nucleophiles
1- Basicity. Salt formation
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NH2 + HCl NH3+Cl-
(CH3CH2)2NH + CH3COOH (CH3CH2)2NH2+, -OOCCH3
anilinium chloride
diethylammonium acetate
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2. Alkylation (ammonolysis of alkyl halides)
• Ammonia and other amines are good nucleophiles
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CH3CH2CH2NH2CH3Cl
CH3CH2CH2NHCH3n-propylamine methyl-n-propylamine
NH22 CH3CH2Br
NEt
Et
aniline N,N-diethylaniline
H2C NH2
benzylamine
(xs) CH3I H2C N
CH3CH3
CH3 Ibenzyltrimethylammonium iodide
CH3CH2CH2NH2CH3Cl
CH3CH2CH2NHCH3n-propylamine methyl-n-propylamine
NH22 CH3CH2Br
NEt
Et
aniline N,N-diethylaniline
H2C NH2
benzylamine
(xs) CH3I H2C N
CH3CH3
CH3 Ibenzyltrimethylammonium iodide
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3- Conversion into amides-Primary and secondary amines react readily with acid chloridesand acid anhydrides to form N-substituted amides.
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-Tertiary amines do not possess a hydrogen atom bonded tonitrogen and do not form amides with acid chlorides and acidanhydrides.
Hinsberg Test:
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Hinsberg Test:unknown amine + benzenesulfonyl chloride, KOH (aq)
- Reacts to produce a clear solution and then gives a ppt uponacidification primary amine.- Reacts to produce a ppt secondary amine.- Doesn’t react tertiary amine.
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4- Ring substitution in aromatic amines- Aromatic amines can undergo substitutions on the ring.• The amino group forms a Lewis acid–base complex with the
AlCl3 catalyst, preventing further reaction• -NH2, -NHR, -NR2 are powerful activating groups and
ortho/para directors• -NHCOR less powerful activator than NH2
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NH2
+ Br2, aq.
NH2Br Br
Brno catalyst neededuse polar solvent
Br2,Fe
Br
HNO3
H2SO4
Br
NO2
+ ortho-
H2/Ni
Br
NH2
polyhalogenation!
NH2CH3
+ CH3CH2Br, AlCl3 NR
Do not confuse the above with the alkylation reaction:
NH2CH3
+ CH3CH2Br
NHCH2CH3CH3
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NH2CH3
+ CH3CH2Br, AlCl3 NR
Do not confuse the above with the alkylation reaction:
NH2CH3
+ CH3CH2Br
NHCH2CH3CH3
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5- Hofmann Elimination• Converts amines into alkenes• NH2
is very a poor leaving group so it converted to analkylammonium ion, which is a good leaving group
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6- Diazonium salts
i- Reactions of Diazonium Salts
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i- Reactions of Diazonium Salts
1- Replacement of nitrogen
-Replacement of the diazonium group is the best general way of introducingF, Cl, Br, I, CN, OH, and H into an aromatic ring.
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(a) Replacement by – Cl, - Br, - CN. Sandmeyer reaction
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(b) Replacement by – I
(c) Replacement by – F
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(d) Replacement by – OH
(e) Replacement by – H
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(e) Replacement by – H
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ii- Coupling- Under the proper conditions, diazonium salts react with certainaromatic compounds to yield products of the general formulaAr – N = N – Ar', called azo compounds, this reaction, knownas coupling.
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