Lab 1: Camphor Reduction Flashcards
What reagent is used in camphor reduction? Why did we use this reagent and what are some safety concerns regarding it?
The reagent is NABH4. We used this because its easy to handle, but it is reactive with water (which is why you keep it capped, it can be deactivated). It can be used with OH reactants
What is the stereochemical outcome of this experiment? Which product is more stable and why?
Exo Attack: Hydride attacks from below to produce borneol (axial OH)
Endo attacl: Hydride attacks from above to produce isoborneol (equatorial OH)
Major product: isoborneol via enzo attacks- more favorable attack bc less steric hinderance.
Why did we not use a reflux condenser for camphor reduction?
The reaction is over so quickly, barely any solvent will have boiled away
Why do we use methylene Chloride for this reaction?
Extracts out extra camphor
What was the purpose of using cold DI water?
To quench the NaBH4 to eliminate its reactivity.
Why did we use methanol as a solvent?
NaBH4 is ionic and only dissolves in polar solvents: aka methanol
Why was isoborneol the major product of this reaction?
It underwent the endo attack because it was less sterically hindered
Would IR be useful in determining whether Borneo or isoborneol is the major product?
No, Both compounds have the same functional groups (OH, C-H)
Would IR be useful in determining if camphor was converted into isoborneol?
Yes, C=O would be present in camphor but O-H would be present in isoborneol
What is a diastereoselective reaction?
When one diastereomer occurs more than the other because whichever attack is more favorable according to the steric
What reagents could turn borneol/isoborneol into camphor?
CrO3, PCC, NAD+ (oxidation)
