Alcohols are synthesized by a wide variety of methods, and the hydroxyl group may be converted to most other functional groups. For these reasons, alcohols are versatile synthetic intermediates. In this chapter, we discuss the physical properties of alcohols and summarize the methods used to synthesize them. | Chapter 10 ©2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Structure and Synthesis of Alcohols Chapter 10 Structure of Water and Methanol Oxygen is sp3 hybridized and tetrahedral. The H—O—H angle in water is °. The C—O—H angle in methyl alcohol is °. Chapter 10 Classification of Alcohols Primary: carbon with —OH is bonded to one other carbon. Secondary: carbon with —OH is bonded to two other carbons. Tertiary: carbon with —OH is bonded to three other carbons. Aromatic (phenol): —OH is bonded to a benzene ring. Chapter 10 Examples of Classifications C H 3 C C H 3 C H 3 O H * C H 3 C H O H C H 2 C H 3 * C H 3 C H C H 3 C H 2 O H * Primary alcohol Secondary alcohol Tertiary alcohol Chapter 10 IUPAC Nomenclature Find the longest carbon chain containing the carbon with the —OH group. Drop the -e from the alkane name, add -ol. Number the chain giving the —OH group the lowest number possible. Number and name all substituents and | Chapter 10 ©2010, Prentice Hall Organic Chemistry, 7th Edition L. G. Wade, Jr. Structure and Synthesis of Alcohols Chapter 10 Structure of Water and Methanol Oxygen is sp3 hybridized and tetrahedral. The H—O—H angle in water is °. The C—O—H angle in methyl alcohol is °. Chapter 10 Classification of Alcohols Primary: carbon with —OH is bonded to one other carbon. Secondary: carbon with —OH is bonded to two other carbons. Tertiary: carbon with —OH is bonded to three other carbons. Aromatic (phenol): —OH is bonded to a benzene ring. Chapter 10 Examples of Classifications C H 3 C C H 3 C H 3 O H * C H 3 C H O H C H 2 C H 3 * C H 3 C H C H 3 C H 2 O H * Primary alcohol Secondary alcohol Tertiary alcohol Chapter 10 IUPAC Nomenclature Find the longest carbon chain containing the carbon with the —OH group. Drop the -e from the alkane name, add -ol. Number the chain giving the —OH group the lowest number possible. Number and name all substituents and write them in alphabetical order. Chapter 10 Examples of Nomenclature 2-methyl-1-propanol 2-methylpropan-1-ol 2-methyl-2-propanol 2-methylpropan-2-ol 2-butanol butan-2-ol C H 3 C C H 3 C H 3 O H C H 3 C H C H 3 C H 2 O H C H 3 C H O H C H 2 C H 3 3 2 1 1 2 3 4 2 1 Chapter 10 Alkenols (Enols) Hydroxyl group takes precedence. Assign the carbon with the —OH the lowest number. End the name in –ol, but also specify that there is a double bond by using the ending –ene before -ol 4-penten-2-ol pent-4-ene-2-ol C H 2 C H C H 2 C H C H 3 O H 5 4 3 2 1 Chapter 10 Naming Priority Acids Esters Aldehydes Ketones Alcohols Amines Alkenes Alkynes Alkanes Ethers Halides Highest ranking Lowest ranking Chapter 10 Hydroxy Substituent When —OH is part of a higher priority class of compound, it is named as hydroxy. 4-hydroxybutanoic acid also known as g-hydroxybutyric acid (GHB) C H 2 C H 2 C H 2 C O O H O H carboxylic acid 4 3 2 1 Chapter 10 Common Names Alcohol can .
