1.1. Paracetamol is a common painkiller that is often manufactured in a multi-step process using 4-aminophenol. Phenol is a common organic chemical, comprised of a benzene ring with one hydroxyl group attached.    

Suggest a two-step synthetic route to form 4-aminophenol from phenol. 

Step 1 of your route should include reagents, conditions, equations to form the electrophile and the identity of the product.

Step 2 of your synthetic route should include the reagents to form 4-aminophenol from your Step 1 product.

1.2. The uncontrolled nitration of phenol can lead to the formation of 2,4,6-trinitrophenol, commonly known as picric acid.

This reaction would require formation of a dinitrophenol intermediate. Draw the possible isomers of this intermediate and name the type of isomerism displayed.

1.3. Paracetamol, figure 1, can be manufactured by the reaction of 4-aminophenol with ethanoyl chloride.

Figure 1

Name and outline the mechanism for this reaction.

1.4. A student started with 3.96 g of ethanoyl chloride (Mr = 78.5).

After preparation of impure paracetamol followed by recrystallisation, the student actually obtained 6.11 g of pure paracetamol (Mr = 151).

Calculate the percentage yield of pure paracetamol from this experiment.