Compare the structure of aspirin, 2.8, with that of salicylic acid, 2.7. What similarities and differences can you see?
Can you identify the group that is carried by aspirin in the corresponding place to the phenol group in the molecule of salicylic acid? Have a look at options in Table 1 .
Which carboxylic acid and alcohol would you use to make isopentyl acetate, 2.9, a constituent of banana oil? (Hint: you need to identify R1 and R2.)
Identify the ester groups in the compounds shown in Figure 2. Write down the reactions that produce each of the esters and thus deduce the structures of the carboxylic acids and alcohols needed to make them.
See if you can pick out the carboxylic acid that is involved in converting the phenol group in salicylic acid into the ester group in aspirin.
Write a list of the main events in ‘the story of aspirin’, from the time of Hippocrates to when Bayer started marketing aspirin.
Step 1 | Willow bark and leaves known to be effective painkillers for thousands of years. Salicin extracted from willow bark during the 1840s. |
Step 2 | Salicin (lead compound) tested and found to be the active ingredient in willow bark and leaves. |
Step 3 | Structure of salicin investigated. |
Step 4 | Salicylic acid synthesised. |
Step 5 | Salicylic acid found to be effective but irritant. |
Step 6 | Sodium salicylate made. Effective for pain relief, not irritant but tasted awful. |
Step 7 | Synthesis of other compounds related to salicylic acid. |
Step 8 | Hofmann tested them (on his father). |
Step 9 | Aspirin emerged as the suitable compound. |
What is the molecular formula of aspirin?
Make a model of a molecule of cyclohexane, a hydrocarbon with molecular formula C6H12 that contains a six-membered ring of carbon atoms. Compare it to a model of benzene and comment on their different shapes.
Each cell in the human body accommodates around 2000 different enzymes but only a small quantity of each one. Why are there so many and why is only a small quantity of each required?