CHEM 10040 The Molecular World 2023/24
Tutorial Problem Set 3
Write your answers on paper, convert them to a single pdf (e.g., using CamScanner) and upload them to
BrightSpace as a single file by 12.00 noon on Monday the 6th of November.
Xarelto (Rivaroxaban)
$6.58 billion
CI
OMe
Eliquis (Apixaban) H2N
$9.871 billion
Shown above are structures of two drugs for cardiovascular disease along with their US sales in
2018. Please draw out one of the structures and answer the questions below with reference to
these structures.
1.
On the structure you have drawn:
a) identify two polar covalent bonds
b) identify one functional group (circle the atoms involved and name the functional group)
2.
In relation to the structure you have chosen:
a) circle the parts of the molecule that are present in both structures.
b) using two of the strategies we have met in lectures draw a modified structure that
could be tested as part of a lead modification strategy if your chosen structure was
a lead compound (i.e., your modified structure should have two modifications).
Highlight where you have made changes by circling them in the structure drawn
and labelling the type of change made.
3.
The $pK_a$ of an acid in water at 20 $^\circ$C is 3.0.
a) Write the equation that relates $K_a$ to $pK_a$.
b) Thus, calculate the $K_a$ of the acid.
c) Is this acid stronger or weaker than acetic acid?
d) Write the equation that relates $K_a$ to concentration of species in solution.