1. Another method for the above reaction starts with 4-aminophenol hydrochloride (the conjugate acid of 4-aminophenol). The treatment of this the hydrochloride salt with sodium ethanoate (acetate) buffer produces 4-aminophenol which is then able to react with ethanoic anhydride as per our method for paracetamol synthesis.

1. Why is 4-aminophenol hydrochloride not suitable for direct reaction with ethanoic anhydride?
2. Draw a mechanism (i.e. curly arrows) showing the deprotonation of 4-aminophenol hydrochloride by sodium ethanoate to form 4-aminophenol (the free base).