General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.1 Chapter 13 Alcohols, Phenols, and Thiols 13.2 Ethers

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.2 Ethers  contain an ─O─ between two carbon groups  that are simple are named by listing the alkyl names in alphabetical order followed by ether CH 3 ─O─CH 3 CH 3 ─CH 2 ─O─CH 3 Dimethyl ether Ethyl methyl ether

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.3 Ethers as Anesthetics Anesthetics  inhibit pain signals to the brain  such as ethyl ether, CH 3 ─CH 2 ─O─CH 2 ─CH 3, were used for over a century but caused nausea and were flammable  developed by the1960s were nonflammable

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.4 Methyl Tert-Butyl Ether (MTBE) Methyl tert-butyl ether  is one of the most produced organic chemicals  is a fuel additive  is used to improve gasoline combustion  use is questioned since the discovery that MTBE has contaminated water supplies

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.5 Cyclic Ethers A cyclic ether  contains an O atom in a carbon ring  is called a heterocyclic compound  typically has 5 (furan) or 6 atoms (pyran) in the ring Furan Tetrahydrofuran Pyran 1,4-Dioxane

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.6 Dioxins Dioxins are  a group of ethers that are highly toxic  formed during forest fires and as industrial by-products  often carcinogenic

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.7 IUPAC Names for Ethers  In the IUPAC system, the shorter alkyl group and the oxygen are named as an alkoxy group attached to the longer alkane. Methoxy propane CH 3 —O—CH 2 —CH 2 —CH  Numbering the longer alkane gives 1-Methoxypropane

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. Guide to Naming Ethers 8

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. Example of Naming Ethers STEP 1 Write the alkane name of the longer chain: Ethane STEP 2 Name the oxygen and smaller alkyl as alkoxy: Ethoxy STEP 3 Number the longer chain and locate the alkoxy group: Ethoxy ethane 9

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.10 Learning Check Name each of the following: A. B.

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.11 Solution Name each of the following: A. Methoxy cyclopentane (cyclopentyl methyl ether) B. 1,4-Dioxane

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.12 Learning Check Draw the condensed structural formula of each of the following compounds: A. 1-Ethoxypropane B. Ethyl methyl ether C. 2-Methoxybutane

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.13 Solution Draw the condensed structural formula of each of the following compounds: A. 1-Ethoxypropane CH 3 —CH 2 —O—CH 2 —CH 2 —CH 3 B. Ethyl methyl ether CH 3 —CH 2 —O—CH 3 C. 2-Methoxybutane