Statins may decompose in the acid present in the stomach. Draw a line through the bond in the atorvastatin structure in Fig. 5.1 that could be cleaved under acidic conditions.
Use the structure to explain why atorvastatin dissolves in water.
Complete the molecular formula of atorvastatin. $\text{C H}_{35}\text{N O F}$
Atorvastatin includes chiral carbon atoms. Circle every chiral carbon atom in Fig. 5.1.
The synthetic preparation of atorvastatin requires the production of a single optical isomer. Suggest why.
The proton ($^1\text{H}$) NMR spectrum of atorvastatin dissolved in $\text{CDCl}_3$ is recorded. Use Table 5.1 to work out the number of hydrogen atoms that could give peaks in the region $\delta = 6.5-13.0$ ppm.
The proton ($^1\text{H}$) NMR spectrum of atorvastatin dissolved in $\text{D}_2\text{O}$ is recorded. Predict how many hydrogen atoms would not show a peak in this spectrum. Explain your answer.
Atorvastatin reacts with an excess of $\text{LiAlH}_4$. Name all the functional groups in atorvastatin that react with $\text{LiAlH}_4$. Name the new functional group that would be formed in each case.