Amines

• Amides


  Acid derivatives that result from the combination of an acid with ammonia or an amine
• Amides


  • They contain the functional group
  • They are among the most stable acid derivatives
  • The nitrogen in amide is not as basic as the nitrogen of ammonia or an amine, because of the electron-withdrawing effect of the carbonyl group
  • This makes it unlikely that the lone pair of electrons on nitrogen can be donated
• Types of amides based on source

  • Carboxamides (organic ones derived from carboxylic acids)
  • Sulfonamides (derived from sulfonic acids)
  • Phosphoramides (derived from phosphoric acids)
• Naming amides


  1. To name the primary amide, first name the corresponding acid

  2. Drop the -ic acid or -oic acid suffix and add the suffix -amide

  3. For secondary and tertiary amides, treat the alkyl groups on nitrogen as substituents, and specify their position by the prefix N-

  4. For acids that are named as alkanecarboxylic acids, the amides are named by using the suffix -carboxamide

  5. Cyclic amides are called Lactams
• Properties of amides


  • Except for formamide (HCONH2) which is a liquid, all simple amides are solids
  • Primary and secondary amides can have strong hydrogen bonds, giving them high boiling and melting points
  • Tertiary amides cannot hydrogen bond, so their boiling points are lower than those of similar size amides
  • Primary, secondary, and tertiary amides can hydrogen-bond with water, therefore the lower members of the series are soluble in water, with borderline solubility occurring in those that have five or six carbon atoms
  • Like the esters, solutions of amides in water usually are neutral—neither acidic nor basic
• The strongly polarized amide N-H hydrogen forms unusually strong hydrogen bonds with the carbonyl oxygen that carries a partial negative charge in the polarized resonance form
• Preparation of amides


  1. The most important ways for producing amides begins with either carboxylic acid or acyl chloride

  2. The reaction between ammonia and an acyl chloride at room temperature

  3. The reaction between a primary amine and an acyl chloride at room temperature
• Ammonia and amines react with acid chlorides to give amides
• NaOH, pyridine, or a second equivalent of amine is used to neutralize the HCl produced to prevent protonation of the amine
• Primary aliphatic amines can be oxidized with potassium dichromate (VI) or permanganate, but they are resistant to oxidation by acidified KMnO4
• Nitrobenzenes can be reduced to form aromatic amines using hydrogen gas and a catalyst such as platinum or palladium.
• If there are multiple amino groups or other functional groups present, the amine group is assigned the lowest possible number in the carbon chain.
• Aniline is the simplest aromatic amine, with one substituent on the benzene ring.
• In the IUPAC system, the longest carbon chain containing the amino group is considered the parent chain for naming amines.
• Amines are named by adding the suffix "-amine" to the name of the alkyl groups attached to the nitrogen atom.
• Aromatic amines are nitrogen-containing compounds that contain an aromatic ring.
• Tertiary amines do not react with acids because the nitrogen is already bonded to three other atoms.
• Secondary amines undergo oxidative deamination when treated with hot concentrated nitric acid
• Tertiary amines do not react with acidified K2Cr2O7 due to their stability towards oxidizing agents
• Aldehydes and ketones can be reduced to alcohols using LiAlH4
• Arylamines can also be prepared from nitriles via reduction with LiAlH4
• Secondary amines can be formed through the reaction of alcohols with ammonia or amines under basic conditions
• Carboxylic acids can be reduced to primary alcohols using NaBH4