Well the only difference between the two structurally is that cyclohexanol is a cycloalkane and phenol is a cycloaklene so I think that you would be able to separate them by distillation. They would be separated by exploiting their boiling points, the lower distilling first. I think you could use fractional distillation (better for substances with smaller boiling point ranges) Since phenols are weakly acidic, the addition of NaOH will make the sodium salt or sodium phenol. This will be soluble in water, while the cyclohexanol will not. If you then add diethyl ether, the cyclohexane will go into that layer (top layer) and the phenol as the sodium salt will stay in the aqueous layer (bottom layer). Solution Well the only difference between the two structurally is that cyclohexanol is a cycloalkane and phenol is a cycloaklene so I think that you would be able to separate them by distillation. They would be separated by exploiting their boiling points, the lower distilling first. I think you could use fractional distillation (better for substances with smaller boiling point ranges) Since phenols are weakly acidic, the addition of NaOH will make the sodium salt or sodium phenol. This will be soluble in water, while the cyclohexanol will not. If you then add diethyl ether, the cyclohexane will go into that layer (top layer) and the phenol as the sodium salt will stay in the aqueous layer (bottom layer)..

1. Well the only difference between the two structurally is that cyclohexanol is a
cycloalkane and phenol is a cycloaklene so I think that you would be able to separate them by
distillation. They would be separated by exploiting their boiling points, the lower distilling first. I
think you could use fractional distillation (better for substances with smaller boiling point
ranges) Since phenols are weakly acidic, the addition of NaOH will make the sodium salt or
sodium phenol. This will be soluble in water, while the cyclohexanol will not. If you then add
diethyl ether, the cyclohexane will go into that layer (top layer) and the phenol as the sodium salt
will stay in the aqueous layer (bottom layer).
Solution
Well the only difference between the two structurally is that cyclohexanol is a
cycloalkane and phenol is a cycloaklene so I think that you would be able to separate them by
distillation. They would be separated by exploiting their boiling points, the lower distilling first. I
think you could use fractional distillation (better for substances with smaller boiling point
ranges) Since phenols are weakly acidic, the addition of NaOH will make the sodium salt or
sodium phenol. This will be soluble in water, while the cyclohexanol will not. If you then add
diethyl ether, the cyclohexane will go into that layer (top layer) and the phenol as the sodium salt
will stay in the aqueous layer (bottom layer).