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Chapter 13 
Ethers and Epoxides; Thiols and Sulfides 
 
Review of Concepts 
Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of 
Chapter 13. Each of the sentences below appears verbatim in the section entitled Review of Concepts and 
Vocabulary. 
 
 Ethers are often used as ____________ for organic reactions. 
 Cyclic polyethers, or __________ ethers, are capable of solvating metal ions in organic 
(nonpolar) solvents. 
 Ethers can be readily prepared from the reaction between an alkoxide ion and an 
______________________, a process called a Williamson ether synthesis. This process works 
best for _________ or ______________ alkyl halides. _____________ alkyl halides are 
significantly less efficient, and ______________ alkyl halides cannot be used. 
 When treated with a strong acid, an ether will undergo acidic _____________ in which it is 
converted into two alkyl halides. 
 When a phenyl ether is cleaved under acidic conditions, the products are _____________ and an 
alkyl halide. 
 Ethers undergo autooxidation in the presence of atmospheric oxygen to form 
________________________. 
 Substituted oxiranes are also called ________________. 
 ______________ can be converted into epoxides by treatment with peroxy acids or via halohydrin 
formation and subsequent epoxidation. 
 _____________ catalysts can be used to achieve the enantioselective epoxidation of allylic 
alcohols. 
 Epoxides will undergo ring-opening reactions in: 1) conditions involving a strong nucleophile, 
or under 2) _____-catalyzed conditions. When a strong nucleophile is used, the nucleophile 
attacks at the ______-substituted position. 
 Sulfur analogs of alcohols contain an SH group rather than an OH group, and are called 
____________. 
 Thiols can be prepared via an SN2 reaction between sodium hydrosulfide (NaSH) and a suitable 
________________________. 
 The sulfur analogs of ethers (thioethers) are called _____________. 
 Sulfides can be prepared from thiols in a process that is essentially the sulfur analog of the 
Williamson ether synthesis, involving a ____________ ion, rather than an alkoxide. 
 
 
 
Review of Skills 
Fill in the blanks and empty boxes below. To verify that your answers are correct, look in your textbook at 
the end of Chapter 13. The answers appear in the section entitled SkillBuilder Review. 
 
13.1 Naming an Ether 
 
 
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