Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 12 Organic Compounds with Oxygen and Sulfur 12.1 Alcohols, Phenols, Thiols, and Ethers 1

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Alcohols An alcohol contains a hydroxyl group (–OH) that replaces a hydrogen atom in a hydrocarbon. A phenol contains a hydroxyl group (–OH) attached to a benzene ring. 2

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Alcohols The names of alcohols in the IUPAC system replace the -e with -ol with common names use the name of the alkyl group followed by alcohol 3 FormulaIUPACCommon Name CH 4 methane CH 3 ─OHmethanolmethyl alcohol CH 3 ─CH 3 ethane CH 3 ─CH 2 ─OHethanolethyl alcohol

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Alcohols 4

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming of Alcohols Step 1 Name the longest carbon chain with the –OH group. Name an aromatic alcohol as a phenol. CH 3  CH 2  CH 2  OH propanol OH CH 3  CH  CH 2  CH 3 butanol CH 3 OH CH 3  CH  CH 2  CH 2  CH  CH 3 hexanol

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming of Alcohols Step 2 Number the chain starting at the end closer to the –OH. CH 3  CH 2  CH 2  OH 1-propanol OH CH 3  CH  CH 2  CH 3 2-butanol CH 3 OH CH 3  CH  CH 2  CH 2  CH  CH 3 2-hexanol

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming of Alcohols Step 3 Give the location and name of each substituent relative to the –OH group. CH 3  CH 2  CH 2  OH 1-propanol OH CH 3  CH  CH 2  CH 3 2-butanol CH 3 OH CH 3  CH  CH 2  CH 2  CH  CH 3 5-methyl-2-hexanol

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Some Typical Alcohols OH | “Rubbing alcohol”CH 3 —CH—CH 3 2-propanol (isopropyl alcohol) Antifreeze HO—CH 2 —CH 2 —OH 1,2-ethanediol (ethylene glycol) OH | GlycerolHO—CH 2 —CH—CH 2 —OH 1,2,3-propanetriol 8

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Name the following compounds: 1. CH 3 —CH 2 —CH 2 —CH 2 —OH OH CH 3 | | 2. CH 3 —CH—CH—CH 2 —CH

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Step 1 Name the longest carbon chain with the – OH group. Name an aromatic alcohol as a phenol. 1. CH 3 —CH 2 —CH 2 —CH 2 —OH butanol OH CH 3 | | 2. CH 3 —CH—CH—CH 2 —CH 3 pentanol 3.cyclopentanol 10

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Step 2 Number the chain starting at the end closer to the – OH. 1. CH 3 —CH 2 —CH 2 —CH 2 —OH 1-butanol OH CH 3 | | 2. CH 3 —CH—CH—CH 2 —CH 3 2-pentanol 3. cyclopentanol 11

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Step 3 Give the location and name of each substituent relative to the – OH group. 1. CH 3 —CH 2 —CH 2 —CH 2 —OH 1-butanol OH CH 3 | | 2. CH 3 —CH—CH—CH 2 —CH 3 3-methyl-2-pentanol 3.cyclopentanol 12

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Phenols in Medicine Phenol is the IUPAC name for benzene with a hydroxyl group used in antiseptics and disinfectants 13 Phenol Resorcinol 4-Hexylresorcinol

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Derivatives of Phenol Compounds of phenol are the active ingredients in the essential oils of cloves, vanilla, nutmeg, and mint. 14

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Phenols Step 1 Name the longest carbon chain with the – OH group. Name an aromatic alcohol as a phenol. 15 phenol phenol

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Phenols Step 2 Number the chain starting at the end closer to the – OH. 16 phenol phenol

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Phenols Step 3 Give the location and name of each substituent relative to the – OH group chlorophenol 4-bromophenol

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Write the structure of each of the following: A. 3-pentanol B. ethyl alcohol C. 4-methylphenol 18

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Write the structure of each of the following: A. 3-pentanol OH | CH 3 —CH 2 —CH—CH 2 —CH 3 B. ethyl alcohol CH 3 —CH 2 —OH C. 4-methylphenol 19 OH CH 3

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Thiols contain sulfur are similar to alcohols contain a thiol (–SH) group often have strong odors are found in cheese, onions, garlic, and oysters are used to detect gas leaks 20

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Thiols Thiols are named in the IUPAC system by adding thiol to the alkane name of the longest carbon chain. 21

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Ethers An ether contains an – O – between two carbon groups has a common name that gives the alkyl names of the attached groups, followed by ether CH 3  O  CH 3 CH 3  CH 2  O  CH 3 22

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Write the structure of the following: A. 3-pentanol B. ethanethiol C. diethyl ether 23

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution OH | A. 3-pentanol CH 3  CH 2  CH  CH 2  CH 3 B. ethanethiol CH 3  CH 2  SH C. diethyl ether CH 3  CH 2  O  CH 2  CH 3 24

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Ethers as Anesthetics Anesthetics inhibit pain signals to the brain like diethyl ether, CH 3  CH 2  O  CH 2  CH 3, were used for over a century, but caused nausea and were flammable developed by the 1960s were nonflammable Cl F F Cl F H H  C  C  O  C  HH  C  C  O  C  H F F F H F H Ethrane (enflurane) Penthrane 25