Cycyclohexene to Cyclohexanol

Data:

Cyclohexene conc. H2SO4 water/boil

* concentrated sulfuric acid ~3.5ml

* water~ 61.7ml

* cyclohexene ~5.05ml

* sodium chloride (small amount)

* potassium carbonate (small amount)

* amount of product (cyclohexanol) 1.7329g

Percent yield= amount of product/amount of starting materials 4.1g/82.143g*1mol=.050 cyclohexene/ 1.7329g/101.159*1mol=.01712 cyclohexanol .01712/.050=.3424*100=34.24%

Cyclohexene BP: 82.98 °C Cyclohexanol BP: 160.84 °C

Cyclohexanol: Literature Peaks: 3450cm-12, 2860cm-12, 1065cm-12,1425cm-12 Literature Descriptions corresponds with literature peaks: Sharp2, Medium2, Strong2, Strong2 Observed Peaks: Absent, 2858.69cm-1, 1034.35cm-1, 1437.46cm-1 Interpretations corresponds with literature peaks and observed peaks except O-H stretching in observed peaks, which was not observed: O-H stretching2, C-H aliphatic2, CO stretch2, CH bending2

Discussion: The preparation of an alcohol with the addition of water to an alkene is to successfully produce cyclohexanol from cyclohexene. The purpose of this lab is to learn how to make an alkene from a secondary alcohol by acid catalyzed hydration. After this procedure has been completed one should be able to set up a steam distillation similar to the one in the eugenol lab and interpret an IR spectrum.

Procedure: Cyclohexene is transformed to cyclohexyl hydrogen sulfate because sulfuric acid is added to the carbon-carbon double bond of cyclohexene. Cyclohexyl hydrogen sulfate is then hydrolyzed to cyclohexanol through steam distillation.

Data Analysis: Cyclohexyl hydrogen sulfate is made from the addition of concentrated sulfuric acid from cyclohexene which is then hydrolyzed to cyclohexanol through boiling and the addition of water; however, our IR spectrum for cyclohexanol was not consistent with the proposed peaks for cyclohexanol. A key functional group was absent, that functional group was an alcohol. Cyclohexanol contains a peak around...