Chapter 14 ? 2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Ethers, Epoxides, and Sulfides Chapter 14 * Ethers Formula is R?O?R???where R and R? are alkyl or aryl. Symmetrical or unsymmetrical O C H 3 C H 3 O C H 3 Chapter 14 Chapter 14 * Structure and Polarity Oxygen is sp3 hybridized. Bent molecular geometry. C?O?C angles is 110?. Polar C?O bonds. Dipole moment of 1.3 D. Chapter 14 Chapter 14 * Boiling Points Similar to alkanes of comparable molecular weight. Chapter 14 Chapter 14 * Hydrogen Bond Acceptor Ethers cannot hydrogen-bond with other ether molecules. Molecules that cannot hydrogen-bond intermolecularly have a lower boiling point. Ether molecules can hydrogen-bond with water and alcohol molecules. Chapter 14 Chapter 14 *