Name ____________________
Experiment #4
Section___________________
Date______________________
Reduction of Camphor
Equation – Draw the overall equation for the reduction of camphor by sodium
borohydride.
Mechanism – In the space provided below show a detailed arrow pushing reaction
for the reduction of camphor.
DataWeight of camphor ___________________
Weight of sodium borohydride __________________
Weight of Product Crude _________________
M.P. Of Product ____________________
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Observations- IR
Attach a copy of your IR to this sheet. Fill in information for the
relavant IR peaks in the chart below.
Position (cm-1)
Peak characteristics
Bond type
Functional group
Based on your IR spectra comment on how well your reaction worked.
H1-NMR Using the included NMR of the product from one of you classmates draw the
structure of the product and asign the protons in this structure to peaks seen in the
spectra.
Calculations 1) Calculate the percent Yield for the formation of alcohol product in your
experiment. Be sure to clearly label the calculations.
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2) Using the given H1-nmr calculate the ratio of the two diasteriomeric products
formed in this reaction. Be sure to clearly label the calculations.
Questions (1) Which diasteriomer is the major product? Why should this be the major product?
(2) When the reaction is complete and acid is added the reaction fizzes. What gas is
being given off?
(3) What are commercial uses for the compounds encountered in this experiment
(camphor, isoborneol and borneol)?
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