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Oxidation of Cinnamyl Alcohol using Pyridinium Chlorochromate

Page history last edited by PBworks 16 years ago

Summary of Procedure:

The reaction mixture is: pyridinium chlorochromate, sodium acetate, molecular sieves, and cinnamyl alcohol.

The reaction is stirred without heating for an hour.

The reaction is monitored by TLC.

The solid is removed by vacuum filtration.

The filtrate is chromatographed on a silica gel column.

Product is analysed by UV, IR, and GC.

 

Positive:

+This is a reaction we are learning in the lecture section.

+The reactant and product smell nice.

+Column chromatography is an important technique

 

Neutral:

±The lab is very TLC intensive. The TLC solvent system should be optimized to give clear indication of what it happening.

±Could a substitute for ethyl ether in the reaction work-up be used?

±GC chromatogram shows that there is an appreciable amount of unreacted alcohol present

 

Negative:

Experiment performed to expectations: Following reaction and column fractions by TLC can be a bit tedious.

 

Inquiry & Extension Ideas:

●Versatile reaction: Many different substrates can be envisioned such as benzyl alcohol, hydrocinnamyl alcohol, or substituted cinnamyl alcohol derivatives.

●Could be explored by leaving out reagents such as NaOAc or molecular sieves. What would be the effect of running the reaction longer or refluxing?

●Could be compared and contrasted with other oxidation methods: peroidic acid, (NH4)Cr2O7, etc...

 

Chromatogram/Spectra Links:

GC of standards and student results (pdf)

 

Student Comments 2008: Oxidation of Cinnamyl Alcohol using Pyridinium Chlorochromate

 

Photo Gallery:

 

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