The major constituents of clove oil are eugenol, eugenyl acetate, and caryophyll
ID: 1004576 • Letter: T
Question
The major constituents of clove oil are eugenol, eugenyl acetate, and caryophyllene: The passage below describes how the three compounds can be separated using techniques and materials similar to those employed in this experiment. Dissolve 1 mL of clove oil in 2 mL of methylene chloride. Add 10 mL of aqueous sodium hydroxide (NaOH) solution. Shake and separate the layers, setting the layer containing the NaOH aside. Obtain a silica-packed chromatography column. Add 2 mL of the non-polar solvent hexane to the column, allow the solvent to just reach the top of the silica packing, then immediately add the clove oil/methylene chloride layer that was separated earlier. Allow the organic layer to just reach the top of the silica packing, then immediately add 10 mL more of hexane. When the solvent just reaches the top of the silica packing, switch solvents by adding 10 mL of the moderately polar solvent acetone.
(1) Which component of clove oil ends up in the layer containing the NaOH? Explain your answer.
(2) Which component of clove oil is pushed down the column by hexane? Explain your answer.
(3) Which component of clove oil is pushed down the column by acetone? Explain your answer.
Explanation / Answer
Eugenol is a phenol and it reacts with NaOH to form sodium phenoxide type of species which is water soluble.
(1) Eugenol component of olive oil will end up in the layer containing NaOH.
(2) Of the two components left, caryophyllnene is more hydrocarbon like and is thus greatly non-polar in nature which dissolves in non-polar solvents such as hexane. So Caryophyllene will be pushed first down the column when hexane is pured in column chromatography.
(3) the most polar components of olive oil of the to left would be eugenyl acetate which is pushed by acetone in column chromatography.
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