Question

3. BORNEOL OXIDATION: SYNTHESIS OF CAMPHOR

a. Draw a detailed electron pushing mechanism for the reaction proposed above.

b. In your aqueous extraction (using the separatory funnel), do you expect the

organic layer to be on top or bottom? What is the crucial physical property that

you need to know, in order to answer this question?

c. Scenario: you are doing your aqueous wash with (mildly basic!) NaHCO3 (step

6), and cap the separatory funnel while chatting with your lab partner about your exciting weekend. The cap flies off and hits the sealing with a loud “bang!”; embarrassment ensues. Please describe the chemical reaction that occurred, with a mechanism and a drawing, and explain how you can prevent this from happening while performing this aqueous wash step. Also: what starting material/solvent do you think this wash (which is basic!) is attempting to remove. (Feel free to research your answer to this).

d. Isoborneol has the opposite configuration at the alcohol carbon carbon relative to borneol (rest of the molecule is identical). As such, are these two molecules enantiomers, diastereomers, achiral/meso, or achiral/non-meso? Consider looking up the structure of isoborneol.

Answer 1

Answer:

b) Answer:

We have to know the solvent density. If the solvent density is more than water, we can see as bottom layer in the separating funnel. Ex: Dichloromethane.

If the solvent density is less, We can see as top layer. Ex : Ethyl acetate.

c) Answer:

In the reaction we used the NaOCl for oxidation, It is the acid. When we are giving the base wash with NaHCO₃ means the reaction is the Acid-Base reaction. The reaction is the exothermic reaction.

NaOCl + NaHCO3 HOCl + Na₂CO₃

d) Answer: