12. Alcohols, Ethers, Epoxides and Thiols

Predict which member of each group is most soluble in water, and explain the reasons for your predictions.

a. butan-1-ol, pentan-1-ol, or propan-2-ol

Draw a condensed structure for each of the following:

g. 1-bromo-1-pentyne

h. 5-methyl-2-cyclohexenol

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

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

Propose mechanisms to show the interchange of protons between ethanol molecules under

(a) acid catalysis.

(b) base catalysis.

Using IUPAC rules, name the following molecules.

(d)

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

a. cyclopentanol or 3-chlorophenol

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

(d) 3-cyclopentylhexan-3-ol

(e) meso-2,4-pentanediol

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

c. 2-chloroethanol or 2,2-dichloroethanol

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

(e)

Propose a mechanism for proton exchange of an alcohol in aqueous base.

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

(c) NaCN