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11-1-12 Chapter 12.docx

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Boston College
CHEM 1161

Chapter 12: 11/01/2012 12.1 Alcohols, Phenols, Thiols, Ethers 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. EX: CH ­3H ­CH2­OH 2         1­propanol                        OH CH ­3H­CH ­CH 2 3 2­butanol           CH3                 CH ­3H­CH ­CH 2CH­CH2        5­3ethyl­2­hexanol Solution 12 Step 3 Give the location and name of each substituent relative to th– OH group. 1. CH —3H —CH 2CH —O2 2 1-butanol OH CH | | 3 2. CH —3H—CH—CH —CH 2 3 3-methyl-2-pentanol OH 3. cyclopentanol Chemistry: An Introduction to General, OrganiCopyright © 2012 by Pearson Education, Inc.on Phenols in Medicine  Phenol is • the IUPAC name for benzene with a hydroxyl group • used in antiseptics and disinfectants OH OH OH OH OH CH CH CH CH CH CH 2 2 2 2 2 3 Phenol Resorcinol 4-Hexylresorcinol Solution 19 Write the structure of each of the following: A. 3-pentanol OH | CH —3H —CH—2H —CH 2 3 B. ethyl alcohol CH 3CH —OH 2 OH C. 4-methylphenol CH 3 Chemistry: An Introduction to General, Organic, aCopyright © 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 • Thiols are named in the IUPAC system by addi g thiol to the alkane name of the longest carbon  chain.  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 • used as anesthetics in the past     C3 ­O­CH3 CH 3CH ­2­CH 3 EX: Write structure A. 2­hexanol  CH3­CH­CH2­CH2­CH2­CH3 B. ethanethiol CH3­CH2­SH C. diethyl ether  CH3­CH2­O­CH2­CH3 12.2 Properties of Alcohols and Ethers  Classification of Alcohols  Classification of alcohols is  determined by the number of alkyl groups attached to the carbon bonded to the hydroxyl  primary (1°)one carbon bond , secondary (2°)2 carbon bonds  , or tertiary 3 carbon  bonds       Primary (1°)          Secondary (2°)          Tertiary (3°)   1 group                      2 groups                 3 groups                       H        CH 3              CH3         |         |          |   CH —3—OH       CH —C—OH    3   CH —C—OH 3         |                     |                |        H                         H                       3    CH Learning Check 3 Classify each alcohol as primary, secondary, or tertiary. OH | A. CH —C3—CH —CH 2 3 B. CH —C3 —CH —2H 2 OH | C. CH —CH —C—CH —CH 3 2 2 3 | CH 3 Chemistry: An Introduction to General, OrganicCopyright © 2012 by Pearson Education, Inc.n Solubility of Alcohols in Water  Alcohols  contain polar ­OH groups and form hydrogen bonds with other alcohol molecules  that have one to three carbons are soluble in water  solubility in water decreases with increasing number of carbons Solubility of Ethers in Water Ethers  do not have a polar ­OH group, but have a C­O­C group  do not form hydrogen bonds  with less than four carbons are slightly soluble in water  with more than four carbons are not soluble in water  up to 4 carbons soluble, after 4 slightly soluble  Solubility of Phenols Phenols  are slightly soluble in water have an ­OH group that can form hydrogen bonds with water   can react with water to produce phenoxide ions  were once used as antiseptics   OH - O 12.3 Reactions of Alcohols and Thiols  Oxidation of 1°Alcohols 3 Alcohols undergo oxidation, increasing the number of carbon and oxygen bonds. Primary alcohols are oxidized to produce an aldehyde. 1 bond to O 2 bonds to O H OH H O | | oxidation | || H—C—C—H H—C—C—H | | | H H H 1° alcohol aldehyd
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