12. Alcohols, Ethers, Epoxides and Thiols

Predict which member of each pair has the higher boiling point, and explain the reasons for your predictions.

a. hexan-1-ol or 3,3-dimethylbutan-1-ol

b. hexan-2-one or hexan-2-ol

Predict which member of each pair will be more soluble in water. Explain the reasons for your answers.

(a) hexan-1-ol or cyclohexanol

(b) heptan-1-ol or 4-methylphenol

(c) 3-ethylhexan-3-ol or octan-2-ol

(d) hexan-2-ol or cyclooctane-1,4-diol

(e)

Draw the structures of the following compounds. (Includes both new and old names.)

(d) 3-cyclopentylhexan-3-ol

(e) meso-2,4-pentanediol

Give systematic (IUPAC) names for the following diols and phenols.

(a)

(b)

Which of the following is the correct IUPAC name for an alcohol with the molecular formula $C_3{H}_{8}O$?