Chapter 12 Organic Compounds with Oxygen and Sulfur

Chapter 12 Organic Compounds with Oxygen and Sulfur 12. 2 Properties of Alcohols, Ethers, and Thiols Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings 1

Boiling Points of Alcohols • contain polar OH groups. • form hydrogen bonds with other alcohol molecules. • have higher boiling points than alkanes and ethers of similar mass. Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings 2

Boiling Points of Ethers • do not have a polar group. • have an O atom, but there is no H attached. • cannot form hydrogen bonds between ether molecules. Copyright © 2005 by Pearson Education, Inc. Publishing as Benjamin Cummings 3

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

Comparing Solubility and Boiling Points Compound Molar Mass Boiling Point (°C) Soluble in Water? Alkane CH 3─CH 2─CH 3 44 -42 No Ether CH 3─O─CH 3 46 -23 Yes Alcohol CH 3─CH 2─OH 46 78 Yes 5

Solubility of Phenol • is soluble in water. • has a hydroxyl group that ionizes slightly (weak acid). • is corrosive and irritating to skin. + H 2 O + H 3 O + 6