Reduction of Camphor to Borneol and Isoborneol
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Hannah Bryson
Reduction of Camphor to Borneol and Isoborneol
Purpose
In this experiment, camphor underwent reduced to form two isomers, borneol and isoborneol, using the reducing agent sodium borohydride. The reduction reaction reduces camphor into borneol, while the oxidation of borneol will revert back to camphor.
Observations
After adding ice cold water to the flask, a solid of crystals formed at the bottom of the flask.
After filtration, we could see white crystals on the filter paper. When the CH4CL2 was added, the mixture became clear.
After boiling off the solvent, a white crystal product was left. Data and Calculation
Reaction mechanism:
4C
10
H
16
O + NaBH
4
+ 4H
2
O ——> 4C
10
H
18
O + NaB(OH)
Calculations:
0.28 g of Camphor
Camphor = 152.23 g/mol
0.28 g/152.23 g/mol
0.00183932 mol of reactant (limiting reagent)
0.25g of sodium borohydride
sodium borohydride = 37.83 g/mol
0.25 g/37.83 g/mol
0.00660851 mol of reactant 250mg of camphor
camphor = 152.23 g/mol
0.00164225 moles of reactant which is also a limiting reagent
Hannah Bryson
250mg of NaBH4
NaBH4 = 37.83g/mol
0.0066085 moles of reactant Borneol and isoborneol predicted mole yield = 0.00164225
Borneol and isoborneol molecular weight = 154.25g/mol
The theoretical yield of product:
(0.00183932 * 154.25 g/mol) =0.284 g of borneol and isoborneol Actual yield of the product:
= 0.35 g
Percent yield of the product:
¿
Actual
Theoretical
×
100%
¿
0.35
0.284
×
100%
= 123%
Melting point of the product:
10
/sec: 220-245
℃
℃
1
/sec: 218-227
℃
℃
Conclusion:
Using the data collected, we can determine that the borneol/isoborneol product we obtained still contained impurities. First and foremost, our percentage yield was abnormally high; this indicated that there was an error within the procedure. It is likely that when evaporating the solvent, not all solvent was evaporated, thus skewing both the percent yield and the melting point. The melting point of borneol is 208
while the melting point of isoborneol is 212-214
.
℃
℃
We did two tests of melting points on our product: one slow and one fast. The melting range of our product was determined to be 218-227
. In comparison to pure borneol and ℃
isoborneol, our melting point was higher. This indicates that there were still impurities left within our product. I do believe, overall, we were successful in obtaining the product; however, we messed up by not allowing all of the solvent to evaporate.
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