Question 3

Salicylic acid (1), and related compounds, methyl salicylate (2), and acetylsalicylic acid (3) are classified as non-steroidal anti-inflammatory drugs (NSAIDS). NSAIDS are valuable because they reduce inflammation, relieve pain, lower fever, and reduce the risk of stroke. Acetylsalicylic acid (Aspirin ®) is the most commonly used drug and it is readily prepared in the laboratory from methyl salicylate (2). Saponification of oil of wintergreen, the natural source of methyl salicylate (2) provides salicylic acid (1), which is readily converted to acetylsalicylic acid by acetylation. What is the major solubility class of salicylic acid (1)?


Salicylic Acid (1) Methyl Salicylate (2) Acetylsalicylic Acid (3)
  1. Salicylic acid is a strongly acidic compound, i.e., a carboxylic acid.
  2. Salicylic acid is a weakly acidic compound, i.e., a phenol.
  3. Salicylic acid is a neutral compound.
  4. Salicylic acid is a basic compound.
Organic Web Chem University of Alberta