Salicylic acid dissociates in water to form a carboxylic acid group, making it more acidic compared to acetylsalicylic acid which has an ester group that is less acidic. The presence of the -OH group in salicylic acid contributes to its higher acidity compared to the -OR group in acetylsalicylic acid.
With 1,5 g of salicylic acid you can obtain theoretically 1,96 g aspirin (acetylsalicylic acid); but in the laboratory (or industry) I remember that the true yield of reaction is a little more than 90 %.
In salicylic acid the hydrogen atom in OH group have a tendency to form hydrogen bonding with oxygen atom in the COO - group thus leaving the H+ ion freely available. In case of ortho methoxy benzoic acid, the possibility of hydrogen bonding is avoided by the presence of strong -CH3 group. Hence salicylic acid is stronger than ortho methoxy benzoic acid.
salicylic acid (an acid) is more polar than methyl salicylate (an ester)
Acylation occurs at the phenol group in salicylic acid due to the higher reactivity of the phenol hydroxyl group compared to the carboxylic acid group. The phenol group is more nucleophilic and readily reacts with acetyl chloride to form acetylsalicylic acid (aspirin). Additionally, the carboxylic acid group can interfere with the reaction due to its ability to form hydrogen bonds, making it less reactive towards acylation.
I assume you mean in water. Salicylate is a salt of salicylic acid. An organic salt is (pretty much) always more soluble in water than its non-salt counterpart. Water is polar, like dissolves like, etc.
Salicylic acid is more polar than aspirin because it has a higher solubility in water due to the presence of a hydroxyl group that enhances its polarity. Aspirin, on the other hand, has an ester functional group, which reduces its overall polarity compared to salicylic acid.
Salicylic acid has a hydroxyl group (-OH) attached to the benzene ring, while benzoic acid has a carboxylic acid group (-COOH) attached to the benzene ring. This difference results in salicylic acid being a phenol derivative and having different chemical properties compared to benzoic acid.
No, it is a completely different chemical compound than aspirin, which is acetylsalicylic acid.
No, aspirin is not an acid in terms of acidity strength. Aspirin is a weak acid called acetylsalicylic acid. Strong acids like hydrochloric acid have a much lower pH and can fully dissociate in solution.
Salicylic acid is a benzene ring with two neighboring functional groups. One is a carboxylic acid (COOH) the other is a hydroxl (OH) When Bicarbonate(HCO3) is added to water with salicylic acid, the -HCO3 pulls the proton off of the hydroxyl making it a salicylate ion. Salicylate ion has a greater solubility than salicylic acid. I think. That's what 1 semester of Ochem will do for you.
Salicylic acid does not dissolves very easily in hot and cold water. This acid is widely used in acne medicine. It is derived from the bark of the willow tree.