Give both the IUPAC name and the common name for each alcohol.

(a) CH₃CH₂CH(OH)CH₃

(b)

(c)

(d) (CH₃)₂CHCH₂CH₂OH

For each molecular formula, draw all the possible constitutional isomers of alcohols with that formula. Give the IUPAC name for each alcohol.

(a) C₃H₈O

For each molecular formula, draw all the possible constitutional isomers of alcohols with that formula. Give the IUPAC name for each alcohol.

(b) C₄H₁₀O

For each molecular formula, draw all the possible constitutional isomers of alcohols with that formula. Give the IUPAC name for each alcohol.

(c) C₃H₆O

For each molecular formula, draw all the possible constitutional isomers of alcohols with that formula. Give the IUPAC name for each alcohol.

(d) C₃H₄O

Give a systematic (IUPAC) name for each diol

(a) CH₃CH(OH)(CH₂)₄CH(OH)C(CH₃)₃

(b) HO-(CH2)₈-OH

(c)

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)

Dimethylamine, (CH₃)₂NH, has a molecular weight of 45 and a boiling point of 7.4 °C. Trimethylamine, (CH₃)₃N, has a higher molecular weight (59) but a lower boiling point (3.5 °C). Explain this apparent discrepancy.

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 will be more acidic. Explain your answers.

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

Without looking them up, rank the following compounds in decreasing order of acidity. These examples represent large classes of compounds that differ widely in acidity.

water, ethanol, 2-chloroethanol, tert-butyl alcohol, ammonia, sulfuric acid, hexane, hex-1-yne, acetic acid

A nitro group (–NO₂) effectively stabilizes a negative charge on an adjacent carbon atom through resonance:

Two of the following nitrophenols are much more acidic than phenol itself. The third compound is only slightly more acidic than phenol. Use resonance structures of the appropriate phenoxide ions to show why two of these anions should be unusually stable.

The following compounds are only slightly soluble in water, but one of them is very soluble in a dilute aqueous solution of sodium hydroxide. The other is still only slightly soluble.

(a) Explain the difference in solubility of these compounds in dilute sodium hydroxide.

The following compounds are only slightly soluble in water, but one of them is very soluble in a dilute aqueous solution of sodium hydroxide. The other is still only slightly soluble.

(b) Show how this difference might be exploited to separate a mixture of these two compounds using a separatory funnel.

Which of the following compounds are suitable solvents for Grignard reactions?

(a) n-hexane

(b) CH₃–O–CH₃

(c) CHCl₃

(d) cyclohexane

(e) benzene

(f) CH₃OCH₂CH₂OCH₃

(g)

(h)

Predict the products of the following reactions.

(a)

(b)

Predict the products of the following reactions.

(c)

(d)

Show how you would synthesize the following primary alcohol by adding an appropriate Grignard reagent to formaldehyde.

(a)

Show how you would synthesize the following primary alcohol by adding an appropriate Grignard reagent to formaldehyde.

(b)

Show how you would synthesize the following primary alcohol by adding an appropriate Grignard reagent to formaldehyde.

(c)

Show two ways you could synthesize each of the following secondary alcohol by adding an appropriate Grignard reagent to an aldehyde.

(a)

Show two ways you could synthesize each of the following secondary alcohol by adding an appropriate Grignard reagent to an aldehyde.

(c)

Show how you would synthesize following tertiary alcohol by adding an appropriate Grignard reagent to a ketone.

b. Ph₃COH

Show how you would synthesize following tertiary alcohol by adding an appropriate Grignard reagent to a ketone.

c. 1-ethylcyclopentanol

Show how you would synthesize following tertiary alcohol by adding an appropriate Grignard reagent to a ketone.

d. 2-cyclopentylpentan-2-ol

Propose a mechanism for the reaction of acetyl chloride with phenylmagnesium bromide to give 1,1-diphenylethanol.

Show how you would add Grignard reagent to acid chloride or ester to synthesize the following alcohols.

a. Ph₃C–OH

Show how you would add Grignard reagent to acid chloride or ester to synthesize the following alcohols.

c. dicyclohexylphenylmethanol