As you watch the video create bullet point procedural list (3 pts)
Complete the table below. Show all calculations (5 pts)
mmoles (1S)-Borneol mmoles Sodium Chloride mmoles Oxone® Theoretical yield of product Crude % yield
Why is this considered a “green” oxidation? You may want to compare this oxidation method with others in your textbook (2 pts)
Write the balanced equation for the reaction performed. (2 pts)
Star all stereogenic centers (chiral carbons) in the borneol starting material and camphor product. (2 pts)
Why does the carbonyl stretching frequency in the infrared spectrum of camphor occur at 1740 cm-1 whereas that of acetophenone (C6H5COCH3) is found at 1680 cm-1 and that for hexanone is found at 1720 cm-1 (3 pts)
Name three ways you could distinguish your product from the starting material. Name the technique and the observations that your would use to make the distinction. (3 pts)
Part 2 Reduction:
This experiment involves the use of a reducing agent (sodium borohydride) for converting a ketone (camphor) to a secondary alcohol (isoborneol) as illustrated in the second step of the two-step oxidation/reduction sequence shown below. The spectra of borneol, camphor, and isoborneol will be compared to detect structural differences and to determine the extent to which the final step produces a pure alcohol isomeric with the starting material.
In principle, the reduction of camphor can give two diastereomeric alcohols, corresponding to reaction of borohydride at the two faces of the C=O bond. Reaction at the top (“exo”) face regenerates the original starting material, borneol. Reaction at the bottom (“endo”) face yields the other diastereomer, isoborneol. You will use NMR to determine the preferred product
Watch the second video
As you watch the video create bullet point procedural list (3 pts)
Complete the table below. Show ALL calculations (3 pts)
mmoles (1S)-Camphor mmoles NaBH4 Theoretical yield of product Mass of product Crude % yield
Below are NMR spectra of the reduction product obtained using LiAlH4 as a reducing agent. Use this data to calculate the relative proportions of the two isomers. (2 pts)
This is the same data for the reduction using NaBH4 as the reducing agent. The picture is not as pretty but the integrations are shown. Calculate the relative portions of the two isomers. (2 pts)
Could optical rotation be used to determine the relative amounts of borneol and isoborneol in the product mixture? Explain why or why not (3 pts)
