12. Alcohols, Ethers, Epoxides and Thiols

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

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)

Predict which member of each pair will be more acidic. Explain your answers.

d. 2,2-dichloropropan-1-ol or 2,2-difluoropropan-1-ol

Predict which member of each pair will be more acidic. Explain your answers.

c. 2-chloroethanol or 2,2-dichloroethanol

Predict which member of each pair is more acidic, and explain the reasons for your predictions.

b. cyclohexanol or cyclohexanethiol

Predict which member of each pair is more acidic, and explain the reasons for your predictions.

a. cyclopentanol or 3-chlorophenol

Which of the following bases would favorably deprotonate a hydroxyl group?

(b) NaOH

Which of the following bases would favorably deprotonate a hydroxyl group?

(c) NaCN

Which of the following bases would favorably deprotonate a hydroxyl group?

(e)

The following molecules were named incorrectly according to IUPAC nomenclature. Give the correct name of these compounds.

(a) 3-oxo-5-methylhexan-2-ol

Using IUPAC rules, name the following molecules.

(d)