Question

give the preparation of aspirin.

Answer 1

Methyl Salicylate is a naturally occurring chemical that is obtained from winter green oil that can be used to synthesize Salicylic Acid. Methyl Salicylate is a phenol with a acetyl group in the ortho position. This carbonyl group can undergo typical carbonyl addition-elimination reactions. An addition elimination reaction occurs at the carbonyl carbon where a nucleophile attacks the highly electrophilic carbonyl carbon. The carbonyl carbon is more electrophilic than the other carbons because the double bonded oxygen withdraws a great amount of the electron density making the carbon highly electropositive. After the nucleophile attacks the carbon, a tetrahedral intermediate with 4 substituents are coming off of the central carbon, one being an oxygen anion, is formed. Then the substituent that is the best leaving group leaves, and the carbonyl group is reformed.