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.

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.

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

Predict the products of the following reactions.

(a)

(b)

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)