1. Chapter 13 Alcohols, Phenols, and Thiols
13.3 Physical Properties of Alcohols, Phenols, and Ethers

2. Boiling Points of Alcohols
contain a strongly electronegative O in the OH groups
form hydrogen bonds between alcohol molecules
have higher boiling points than alkanes and ethers of similar mass

3. Boiling Points of Ethers
have an O atom, but no H is attached
cannot form hydrogen bonds between ether molecules
have boiling points similar to alkanes of similar mass

4. Solubility of Alcohols and Ethers in Water
Alcohols and ethers are more soluble in water than are alkanes because the oxygen atom hydrogen bonds with water.
Alcohols with 1–4 C atoms are soluble, but alcohols with 5 or more C atoms are not.

5. Comparing Solubility and Boiling Points

6. Solubility of Phenol Phenol is soluble in water
has a hydroxyl group that ionizes slightly (so is a weak acid)
is corrosive and irritating to the skin
+ H2O H3O+

7. Learning Check Which compound would have the higher boiling
point, ethyl methyl ether or 1-propanol? Explain.

8. Solution Which compound would have the higher boiling
point, ethyl methyl ether or 1-propanol? Explain.
1-propanol would have the higher boiling point because
alcohol molecules can form hydrogen bonds, but ether
molecules cannot.

9. Learning Check
Which compound would be more soluble in water, ethanol or 2-pentanol? Explain.

10. Solution
Which compound would be more soluble in water, ethanol or 2-pentanol? Explain.
Ethanol. An alcohol with two carbons in its chain
is more soluble than one with 5 carbons. The longer
alkyl chain diminishes the effect of the –OH group.