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Borneol
Bicyclic compound that is found in plants and used in medicine
Can be oxidized into camphor
Camphor
bicyclic compound that has a carbonyl group
Why is using chromate solutions to oxidize secondary alcohols dangerous?
They are carcinogenic and caustic
What solution is used in this experiment to turn borneol into camphor?
Hypochlorous acid
Why is hypochlorous acid used as an oxidization agent?
it serves as a safer alternative to chromate solutions (which are dangerous)
How will hypochlorous acid be generated?
Hypochlorous acid will be generated by treating bleach with with acetic acid
Why is it important to use a large amount of sodium hypochlorite?
In the past, the reaction did not properly go to completion, leading to some unoxidized borneol product. Adding a large amount of sodium hypochlorite ensures complete oxidization
What is the other solution that can be used for this experiment to turn borneol into camphor?
Oxone
How do you do the procedure to turn borneol into camphor in the original method?
In a round bottom flask add borneol, acetone and glacial acetic acid. warm this mixture in a warm water bath. Add 2 ml of sodium hypochlorite every 4 minutes
What do we wash the product with in original procedure 6A?
we wash the product with saturated sodium bicarbonate. gently shake until no more bubbles are seen
What solution is used for the first extraction?
Ethyl acetate
What solution is used for the second extraction in the original 6A procedure?
aqueous sodium bisulfate and water
What do we dry the camphor solution with?
sodium sulfate
What is the procedure for alternate part 6A?
in a round bottom flask add borneol, ethyl acetate. while its stirring add in equal molar equivalents of oxone, sodium chloride and water. stir for 50 minutes. add additional sodium chloride and stir for an additional 10 minutes. add some more water to the salts, extract with methylene chloride and dry over sodium sulfate
What is the procedure for part 6B?
add the camphor product along with other reagents into a flask and heat it for 2 minutes. let it cool and then add ice water, vacuum filtrate, dissolve solid and dry the product and decant into an empty beaker to evaporate
Where is the NMR peak for borneol?
4.0 ppm
Where is the NMR peak for isoborneol?
3.6 ppm
What is the role of sodium borohydride in part B?
it acts as a reducing agent to reduce camphor into isoborneol
Why is it important to add ice water to the mixture in part B?
Ice water is added to prevent the formation of unwanted product
What is the purpose of the vacuum filtration in part B?
It is to separate the white solid from the liquid phase
Why is it important to add sodium hypochlorite dropwise every 4 minutes in original part A?
Adding sodium hypochlorite ensures that it remains a controlled reaction and oxidized properly
Why is glacial acetic acid used in original part A?
Glacial acetic acid is used to help with the formation of hypochlorous acid
