PHARMACEUTICAL CHEMISTRY – TUTORIAL 1: 5th October, 2016

1. a) Draw all the structural isomers of butene.

b) Which of the structures in (a) above would exhibit stereoisomerism?
c) Give an appropriate E/Z nomenclature for the geometric isomers in question 1b above.

2. Determine if the molecules below have conjugation, aromaticity, both, or neither.

3. Consider the chemical reaction below and answer the questions that follow:

a) What would be the major organic product assuming the reaction undergoes SN1
reaction?
b) Write the stepwise mechanism for the above reaction.

4. Which of the following two amines is more basic and why?

5. How many distinct alkenes can result from E2 elimination of the compound below?
Which one would be the most predominant and why?

6. Provide a detailed, stepwise mechanism for the reaction below. State whether the reaction
is SN1, SN2, E1 or E2.