12. Alcohols, Ethers, Epoxides and Thiols

Draw the correct structure from the following IUPAC names:

(a) (4R,2Z)-4-methylhex-2-en-1-ol

Draw the correct structure from the following IUPAC names:

(c) (1S,4R)-4-bromocyclohex-2-en-1-ol

Draw a condensed structure for each of the following:

g. 1-bromo-1-pentyne

h. 5-methyl-2-cyclohexenol

Give a systematic (IUPAC) name for each alcohol. Classify each as primary, secondary, or tertiary.

(f)

(g)

Give a systematic (IUPAC) name for each diol

(a) CH₃CH(OH)(CH₂)₄CH(OH)C(CH₃)₃

(b) HO-(CH2)₈-OH

(c)

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

Give a systematic (IUPAC) name for each diol

(d)

(e)

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

(d) Et₃N

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

(a)

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

(a) acid catalysis.

(b) base catalysis.

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