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Organic Chemistry - Amines

Sat Feb 4, 2023

Amine can refer to:
  1. Amines - a class of organic compounds that contain nitro group Chemical properties of amines include:
  1. Basicity: Amines are basic in nature due to the presence of a lone pair of electrons on the nitrogen atom, which can accept protons.
  2. Solubility: Amines are soluble in water due to the hydrogen bonding between the nitrogen atom and water molecules. The solubility of amines decreases with increasing molecular weight.
  3. Reactivity: Amines can react with alkyl halides, acid chlorides, and esters to form amides, imides, and amido halides. They can also react with nitrous acid to form diazonium salts, which can undergo substitution reactions.
  4. Aromaticity: Some amines can act as weak acids and participate in aromatic substitution reactions.
  5. Electrophilic substitution: Primary amines can undergo electrophilic substitution reactions, such as alkylation and acylation.
  6. Hydrogen bonding: Amines have a higher boiling point compared to similar-sized alkanes due to the presence of hydrogen bonding between the nitrogen atom and the hydrogen atoms.
  7. Tautomerism: Some amines exhibit tautomerism, which is the rapid interconversion of two or more constitutional isomers.
Write chemical reaction how we prepare amine
There are several methods for preparing amines, including:
  1. Reduction of nitriles: Nitriles (RCN) can be reduced to primary amines (RNH2) using hydrogen gas and a metal catalyst, such as nickel or palladium.
Reaction: RCN + H2 → RNH2
  1. Reduction of amides: Amides (RCONH2) can be reduced to primary amines (RNH2) using lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4).
Reaction: RCONH2 + LiAlH4 → RNH2 + LiAl(OH)4
  1. Ammonolysis of alkyl halides: Alkyl halides (RX) can be reacted with ammonia (NH3) to form primary amines (RNH2).
Reaction: RX + NH3 → RNH2
  1. Mannich reaction: A Mannich reaction involves the reaction of a primary amine (RNH2), formaldehyde (HCHO), and an alkyl or aryl aldehyde to form a new amine (RC(O)NR2).
Reaction: RNH2 + HCHO + R'CHO → RC(O)NR2 + H2O
  1. Gabriel synthesis: The Gabriel synthesis is a method for preparing primary amines by reacting phthalimide (C6H4(CO)2NH) with an alkyl halide (RX) in the presence of sodium hydroxide (NaOH).
Reaction: C6H4(CO)2NH + RX + NN→ RNH2

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