Chemistry · MU Pleven

Characteristic  of  the  heterofunctional  derivatives  of  hydrocarbons.  Aminoalcohols,  aminophenols and their derivatives with medico–biological importance.

Covers how difunctional compounds behave and how they are named, using a priority order and a prefix-suffix table for common groups. It then describes aminoalcohols such as ethanolamine, choline, sphingosine and taurine, with their biological roles, followed by physiologically active amino alcohols like the catecholamines and synthetic phenethylamines such as amphetamines. The final part addresses para-aminophenol and its derivatives, including acetanilide, phenacetin and paracetamol, and how alkyl and acyl substitution affects toxicity.

Inside: 4 sections · 23 labelled pictures · 1 table · 14 flashcards · 11 min

Topic 30 of 47 in the MU Pleven syllabus for Chemistry (Medicine, Year 1). The free AceMed note covers it in 4 sections, about 1,580 words (11 min of reading), with 14 flashcards.

In this note

  1. AMINOALCOHOLS, AMINOPHENOLS AND THEIR DERIVATIVES
  2. II. AMINO ALCOHOLS
  3. III. PHYSIOLOGICALLY ACTIVE AMINO ALCOHOLS AND AMINO PHENOLS
  4. IV. PARA-AMINOPHENOL AND ITS DERIVATIVES

AMINOALCOHOLS, AMINOPHENOLS AND THEIR DERIVATIVES

I. INTRODUCTION. To a first approximation, the chemical properties of di- and polyfunctional compounds are the sum of those of the individual functions. However, in many cases the two functional groups interact in such a way as to give the compound chemical properties that are not observed with the simple monofunctional compounds. In other cases the chemical properties of a difunctional compound are similar to those of corresponding monofunctional compounds in a qualitative respect, but not in a quantitative sense. Special difunctional compounds are aminoalcohols (NH2, OH), aminophenols (NH2, OH), hydroxy acids (OH, COOH), aldehyde acids (CHO, COOH), keto acids (>CO, COOH), amino acids (NH2, COOH) and carbohydrates (OH, CHO, >CO).

When a compound contains two different functional groups, one of the groups (the principal function) is usually expected suffix (ending) and the other as a prefix, for example 3-hydroxypropanoic acid is the correct name because the carboxyl functional group has higher priority than hydroxyl group.

In the naming of a difunctional compound, a choice must be made as to which group isthe principal function. Thegeneral accepted order for naming these compounds is:

  1. 1. Carboxylic acids
  2. 2. Anhydrides
  3. 3. Sulfonic acid
  4. 4. Esters
  5. 5. Acid halides
  6. 6. Amides
  7. 7. Nitriles
  8. 8. Aldehydes followed by thioaldehydes
  9. 9. Ketones followed by thioketones
  10. 10. Alcohols and Phenols followed by sulfides
  11. 11. Thiol
  12. 12. Amine
  13. 13. Ethers followed by sulfides
  14. 14. Alkynes
  15. 15. Alkenes

Since alkenes and alkynes cannot be designated by prefixes, they are always indicated by a second suffix, which is placed before the final suffix of any functional group that is higher in the order, e.g. 2-amino-3-butenoic acid.

The following table contains a list of common functions with the appropriate prefix and suffix used to designate each one in a name of a polyfunctional derivative.

The highest precedence group takes the suffix, with all others taking the prefix form.

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