12. Alcohols, Ethers, Epoxides and Thiols

Draw the correct structure from the following IUPAC names:

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

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

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

(a)

(b)

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

(d) Et₃N

Draw the correct structure from the following IUPAC names:

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

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

(f)

(g)

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

Give a systematic (IUPAC) name for each diol

(d)

(e)

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)

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

(b) NaOH

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

(a)

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

b. cyclohexanol or cyclohexanethiol

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 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