1. (a) Consider the chemotherapy drug (1) shown below.
(i) Circle and label five different oxygen-containing functional groups present.
For this I found amide, alcohol, ester, ketone, ether, but I'm not sure if there are more
(ii) Identify ALL the chiral centres present in compound (1) with a star *.
I found 1 with the alcohol group attached to the amide group, and another on the ring next to the ester structure to the right of the first one. I'm not sure of there are more
(iii) Select ANY ONE of the chiral centres you have identified in part (ii) above, label with a letter Z and assign the correct Cahn-Ingold-Prelog (R, S) configuration. In your answer include the assignment of priorities.
i used the first chiral center and I got S.
(b) The following heterocyclic compound (2) is currently being evaluated in numerous clinical trials to
investigate its potential as a possible treatment for COVID-19. Using your knowledge and the
criteria for aromaticity in your response, determine and discuss if the compound is aromatic, non-
aromatic or anti-aromatic.
Using Hukel's rule, i got the structure as non aromatic since it didnt follow the rule, but I may have missed a Pi electron
(c) For the following chemical species (3), draw all the resonance structures that are possible using
appropriate diagrams and curved arrows to show the movement of electrons.
I have trouble with this so I'm not sure how to do this.
(d) In one of your chemistry laboratory exercises, you were asked to perform a hydrohalogenation reaction with starting material A and HCl. Instead of producing the product you expected, B, you obtained a mixture of two products B and C in unequal amounts of which C was formed in a much higher yield.
(i) Suggest a detailed reaction mechanism to explain the formation of the unexpected major product C.
(ii) Concisely explain why this unexpected major product C predominated in your reaction.
No idea here either