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Amines

Topic Review on "Title":

Background for Amines
Amines are classified by the number of carbons directly attached to the nitrogen.  A primary amine contains one alkyl group attached to the nitrogen.  A secondary amine contains two alkyl groups attached to the nitrogen.  A tertiary amine contains three alkyl groups attached to the nitrogen.  A quaternary amine contains four alkyl groups attached to the nitrogen.  Primary, secondary, and tertiary amines are sp3 hybridized, have a trigonal pyramidal shape, and a bond angle of 107o.  Quaternary amines are sp3 hybridized, have a tetrahedral shape, and a bond angle of 109.5o.  Primary and secondary amines have intermolecular hydrogen bonding.  Primary and secondary amines have boiling points and melting points between ethers and alcohols.  Tertiary amines have boiling points and melting points lower than primary and secondary amines with similar molecular weights.  Amines have fishy smells.

IUPAC Nomenclature for Amines
For the IUPAC nomenclature, the longest continuous carbon chain is the parent compound.  Number the chain so that the C-N bond has the lowest possible number.  From the alkyl prefixes, use Aanamine@ for amines.  Give the location of the attachment of the N to the parent amine.  Name and number substituents. 

Common Nomenclature for Amines
For the common nomenclature, an amine is named with the alkyl groups first, then Aamine.@  Alphabetize the groups.  Name amine salts as ammonium salts.

Synthesis of Amines
Nitro compounds are reduced to primary amines with hydrogen with a catalyst (nickel, palladium, or platinum).  Nitro compounds are reduced to primary amines with acid and a metal (iron, zinc, or tin).  Nitriles are reduced to primary amines with hydrogen and nickel.  Amides are reduced with lithium aluminum hydride, followed by hydrolysis, to amines.  Alkyl halides react with ammonia or amines, followed by loss of hydrogen halide, to yield amines.  Aldehydes and ketones react with hydroxylamine, followed by reductive amination, to form primary amines.  Possible reduction reagents are hydrogen and nickel; lithium aluminum hydride and hydrolysis; and zinc and hydrochloric acid.  Aldehydes and ketones react with primary amines, followed by reductive amination, to form secondary amines.  Reduction reagents include hydrogen and nickel or lithium aluminum hydride, followed by hydronium ion.  Aldehydes and ketones react with secondary amines, followed by reductive amination with sodium triacetoxyborohydride, to yield tertiary amines

Reactions of Amines
Amines react with hydrogen halides to form ammonium salts. Aldehydes and ketones react with ammonia derivatives, in the presence of acid, to form imine derivatives.  Acid chlorides react with amines to form amides. Sulfonyl chlorides react with amines to yield sulfonamides.


Rapid Study Kit for "Title":
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Core Concept Tutorial Problem Solving Drill Review Cheat Sheet

"Title" Tutorial Summary :
Amines can be described by classification, shape, properties, and uses.  Amines are classified by the number of alkyl groups attached directly to the nitrogen.  The rules for naming the amines by IUPAC and common nomenclature are listed.  The nomenclature of amine salts is described.  Nitro compounds and nitriles are reduced to amines.  Amides are reduced with lithium aluminum hydride to yield amines.  Amines react with alkyl halides to produce larger amines.  Aldehydes and ketones react with hydroxylamine, then reduced, to give primary amines.  Primary amines react with aldehydes and ketones, followed by reduction, to give secondary amines.  Secondary amines react with aldehydes and ketones, followed by reduction, to give tertiary amines.  Hydrogen halide reacts with amines to form ammonium salts.  Ammonia derivatives react with aldehydes and ketones to yield imines.

Tutorial Features:

This tutorial provides the comprehensive coverage of the chapter with easy introduction and simple illustration. It features:

  • Concept map showing interconnections of new concepts in this tutorial and those previously introduced.
  • Definition slides introduce terms as they are needed.
  • Visual representation of concepts.
  • Use of colors to emphasis points.
  • Outline of chemical classification, shape, properties, and uses.
  • Easy-to-follow animations of stated rules of nomenclature.
  • Detailed stepwise explanations and animations of reactions and mechanisms.
  • Examples worked out step-by-step throughout the tutorial.
  • A concise summary is given at the conclusion of the tutorial.

"Title" Topic List:

Background Information for Amines

  • Classification
  • Shape
  • Properties
  • Uses

Nomenclature of Amines

  • IUPAC
  • Common
  • Amine Salts

Synthesis of Amines

  • Reduction of Nitro Compounds
  • Reduction of Nitriles
  • Reduction of Amides
  • Alkylation of Amines
  • Reduction Amination of Aldehydes and Ketones

Reactions of Amines

  • Reaction with Hydrogen Halide
  • Reaction with Aldehydes and Ketones
  • Acylation
  • Reaction with Sulfonyl Chloride


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