Quiz 1: Oxidation of (1S)-(-)-Borneol to (1S)-(-)-Camphor Flashcards
The purpose of acetic acid in the following reaction (of 1s-(-)-borneol to 1s-(-)-camphor is:
A. It is the solvent.
B. It assists in the generation of hypochlorous acid (HOCl).
C. Both a, it is the solvent, and b, it assists in the generation of hypochlorous acid.
D. neither
C
How many spots on the TLC plate exist if 50% of the chemical rxn (borneol → camphor) has reacted?
A. 1
B. 2
C. 3
D. 4
B
Isoborneol is spotted on TLC with a 4:6 ratio of hexane:EtOAc. What will the outcome be?
A. camphor has the lower Rf value bc it is more polar
B. borneol has the lower Rf value bc it is more polar
C. camphor has the higher Rf value bc it is more polar
D. borneol has the higher Rf value bc it is less polar
B
In organic chemistry, oxidation is defined as:
A. gain of electrons
B. loss of hydrogen
C. loss of electrons
D. both B & C
D
What is the purpose of using the 5% sodium bisulfite solution to wash the organic layer during the extraction work-up?
A. to remove remaining acid
B. to remove remaining hypochlorite
C. to pre-dry the organic layer
D. to remove the organic impurities
B
Where is the C-O stretch in IR spectrometry?
1700-1750 cm^-1
Where is the OH stretch of borneol in IR spectroscopy?
3300-3350 cm^-1
What is an alternative to DCM?
A. acetone
B. ethanol
C. diethyl ether
D. water
C
What is the best method monitoring the reaction progress during oxidation reaction of borneol –> camphor?
A. column chromatography
B. TLC
C. crystallization
D. extraction
B
The reaction of borneol → camphor is monitored by TLC using silica plate and 2:1 hexane : EtOAc as a solvent. Which is true?
A. product has a lower Rf bc it’s less polar
B. reactant has a higher Rf bc it’s less polar
C. product has a higher Rf bc it’s more polar
D. reactant has a lower Rf bc it’s more polar
D (reactant = borneol)
Where is the alkyl C-H stretch on IR spectrum of camphor/borneol?
A. 1650-1550 cm^-1
B. 2950-2850 cm^-1
B. 2950-2850 cm^-1
Which functional group is synthesized in the product, camphor?
ketone
Start with 0.12 g of borneol (MW = 154.25 g/mol). How much camphor (MW = 152.23 g/mol) in g could you make?
0.12 g
(see picture of borneol and camphor on a TLC plate) Which has a higher Rf value?
A. camphor has the higher Rf value bc it is more polar
B. borneol has the higher Rf value bc it is more polar
C. camphor has the higher Rf value bc it is less polar
D. borneol has the higher Rf value bc it is less polar
C
Where would you expect to see an absorption in the IR that would indicate that you have product and no longer reactant? (approx. wavenumber value)?
C=O (carbonyl stretch) at 1710 cm^-1
