2. Molecular Representations

Arrange the following organic compounds in order from most soluble to least soluble in water: $\mathrm{CH}{3}_{O}H$, $\mathrm{CH}{3}_{\mathrm{CH}}{2}_{\mathrm{OH}}$, $\mathrm{CH}{3}_{\mathrm{CH}}{2}_{\mathrm{CH}}{2}_{\mathrm{OH}}$, $\mathrm{CH}{3}_{\mathrm{CH}}{2}_{\mathrm{CH}}{2}_{\mathrm{CH}}{2}_{\mathrm{OH}}$.

Which of the following reactions would benefit from micellar technology (Figure 7.10), allowing them to be run in water?

(a)

(b)

(c)

Classify the following molecules as hydrophilic, hydrophobic, lipophilic, or lipophobic. Each molecule should have two classifications.

(a)

Would you expect the following molecule to be miscible in an aqueous solution?

Would you expect the following molecule to be miscible in an aqueous solution?

In which solvent would cyclohexane have the lowest solubility: 1-pentanol, diethyl ether, ethanol, or hexane?

In each pair,

(i) choose the compound that is most soluble in water.

(ii) Within each pair, which is most soluble in nonpolar solvents?

(a)

Circle the member of each pair that is more soluble in water.

a. CH₃CH₂OCH₂CH₃ or CH₃CH₂CH₂CH₂CH₃

b. CH₃CH₂OCH₂CH₃ or CH₃CH₂CH₂OH

c. CH₃CH₂NHCH₃ or CH₃CH₂CH₂CH₃

d. CH₃CH₂OH or CH₃CH₂CH₂CH₂OH

e.

Would you expect the following molecule to be miscible in an aqueous solution?

Which of the following factors is most important in determining the solubility of a compound in $H_{2}O$?

Classify the following molecules as hydrophilic, hydrophobic, lipophilic, or lipophobic. Each molecule should have two classifications.

(b)

Which of the following methods is commonly used to determine the solubility of a compound in organic chemistry?

Rank the given solvents in decreasing order of their ability to dissolve each compound.

Solutes:

(a) NaOAc

(b)

(c)

Solvents:

ethyl ether

water

ethanol

dichloromethane

Explain why amino acids, unlike most amines and carboxylic acids, are insoluble in diethyl ether.

Methoxychlor is an insecticide that was intended to take DDT’s place because it is not as soluble in fatty tissues and is more readily biodegradable. It, too, can accumulate in the environment, however, so its use was also banned—in 2002 in the European Union and in 2003 in the United States. Why is methoxychlor less soluble in fatty tissues than DDT?