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Amines (organic ammonia) :NH 3 :NH 2 R or RNH 2 1 o amine(R may be Ar) :NHR 2 or R 2 NH 2 o amine :NR 3 or R 3 N3 o amine - PowerPoint PPT Presentation


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Amines (organic ammonia) :NH 3 :NH 2 R or RNH 2 1 o amine(R may be Ar) :NHR 2 or R 2 NH 2 o amine :NR 3 or R 3 N3 o amine NR 4 + 4 o ammonium salt.

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Amines (organic ammonia) :NH 3 :NH 2 R or RNH 2 1 o amine(R may be Ar) :NHR 2 or R 2 NH 2 o amine :NR 3 or R 3 N3 o amine

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Amines

(organic ammonia) :NH3

:NH2R or RNH21o amine(R may be Ar)

:NHR2 or R2NH2o amine

:NR3 or R3N3o amine

NR4+4o ammonium salt


NB amines are classified by the class of the nitrogen, primary amines have one carbon bonded to N, secondary amines have two carbons attached directly to the N, etc.

Nomenclature.

Common aliphatic amines are named as “alkylamines”


Salts of amines: change amine  ammonium + anion

change aniline  anilinium + anion

CH3CH2CH2NH3+Cl-

n-propylammonium chloride

(C6H5NH3)2SO4

anilinium sulfate


Amines, physical properties:

Nitrogen is sp3 hybridized, amines are polar

and can hydrogen bond.

mp/bp are relatively high for covalent substances

amines are basic and will turn litmus blue

insoluble in water (except for four-carbons or less)

soluble in 5% HCl

“fishy” smell 


RNH2 + HCl  RNH3+ + Cl-

water water

insoluble soluble

RNH3+ + OH- RNH2 + H2O

water water

solubleinsoluble

1. test for amines

2. can be used to separate amines from neutral

or acidic organic compounds


  • Amines, syntheses:

    • Reduction of nitro compounds

  • Ar-NO2 + H2,Ni  Ar-NH2

    • Ammonolysis of 1o or methyl halides

      • R-X + NH3 R-NH2

    • Reductive amination

    • R2C=O + NH3, H2, Ni  R2CHNH2

    • Reduction of nitriles

    • R-CN + 2 H2, Ni  RCH2NH2

    • Hofmann degradation of amides

    • RCONH2 + KOBr  RNH2


1. Reduction of nitro compounds:


  • Ammonolysis of 1o or methyl halides.


3. Reductive amination:

Avoids E2


Reductive amination via the imine.


  • Reduction of nitriles

  • R-CN + 2 H2, catalyst  R-CH2NH2

  • 1o amine

  • R-X + NaCN  R-CN  RCH2NH2

  • primary amine with one additional carbon

  • (R must be 1o or methyl)


5. Hofmann degradation of amides


  • Amines, syntheses:

    • Reduction of nitro compounds1o Ar

  • Ar-NO2 + H2,Ni  Ar-NH2

    • Ammonolysis of 1o or methyl halidesR-X = 1o,CH3

      • R-X + NH3 R-NH2

    • Reductive aminationavoids E2

    • R2C=O + NH3, H2, Ni  R2CHNH2

    • Reduction of nitriles+ 1 carbon

    • R-CN + 2 H2, Ni  RCH2NH2

    • Hofmann degradation of amides- 1 carbon

    • RCONH2 + KOBr  RNH2


Outline possible laboratory syntheses for each of the following amines, starting with toluene. Use a different method for each compound.

First decide which method you are going to use for which compound…


1. nitration

5. Hofmann degradation

4. Reduction of nitrile

3. Reductive amination

2. ammonolysis


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