Hello, Just finished a lab on reducing a ketone to a secondary alcohol using NaB

Question

Hello,

Just finished a lab on reducing a ketone to a secondary alcohol using NaBH4.

Here is a figure:

And heres a pic of the mechanism..

We used gas chromatography with this anhydrous reaction as the techniques of experiment. The gas chromatography allows us to determine the ratio of cis and trans products from this reaction (cis = minor and trans = major products). WHAT OTHER SEPARATION TECHNIQUE COULD WE HAVE USED TO determine the same thing? (NOTE: polarities are the same so column chromatography won't work here)

Explanation / Answer

I can give two methods

1. HPLC

2.Crystallization

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