© 2013 Pearson Education, Inc. Fundamentals of General, Organic, and Biological Chemistry, 7e John McMurry, David S. Ballantine, Carl A. Hoeger, Virginia E. Peterson Worked Example 14.1 Naming Organic Compounds: Alcohols First, identify the longest carbon chain, and number the carbon atoms beginning at the end nearer the —OH group. The longest chain attached to the —OH has 5 carbon atoms: Analysis Give the systematic name of the following alcohol, and classify it as primary, secondary, or tertiary: Since the —OH group is bonded to a carbon atom that has three alkyl substituents, this is a tertiary alcohol. Solution Next, identify and number the hydroxyl group and the substituents. Finally, write the name of the compound.

© 2013 Pearson Education, Inc. Fundamentals of General, Organic, and Biological Chemistry, 7e John McMurry, David S. Ballantine, Carl A. Hoeger, Virginia E. Peterson Worked Example 14.2 Organic Reactions: Dehydration Find the hydrogens on carbons next to the OH-bearing carbon, and rewrite the structure to emphasize these hydrogens: Analysis What products would you expect from the following dehydration reaction? Which product will be major and which will be minor? Then, remove the possible combinations of —H and —OH, drawing a double bond each —H and — OH could be removed: Finally, determine which alkene has the larger number of alkyl substituents on its double-bond carbons and is therefore the major product.

© 2013 Pearson Education, Inc. Fundamentals of General, Organic, and Biological Chemistry, 7e John McMurry, David S. Ballantine, Carl A. Hoeger, Virginia E. Peterson Solution Worked Example 14.2 Organic Reactions: Dehydration Continued

© 2013 Pearson Education, Inc. Fundamentals of General, Organic, and Biological Chemistry, 7e John McMurry, David S. Ballantine, Carl A. Hoeger, Virginia E. Peterson Worked Example 14.3 Organic Reactions: Dehydration The double bond in the alkene is formed by removing —H and —OH from adjacent carbons of the starting alcohol. This removal occurs in two possible ways, depending on which carbon is bonded to the —OH and to the —H. Analysis Which alcohol(s) yield 4-methyl-2-hexene on dehydration? Are there any other alkenes that arise from dehydration of these alcohols? Dehydration of 4-methyl-2-hexanol yields 4-methyl-2-hexene as the major product, along with 4-methyl-1-hexene. Dehydration of 4-methyl-3-hexanol also gives 4-methyl-2-hexene but as the minor product, along with 3-methyl-3- hexene as the major product. Solution

© 2013 Pearson Education, Inc. Fundamentals of General, Organic, and Biological Chemistry, 7e John McMurry, David S. Ballantine, Carl A. Hoeger, Virginia E. Peterson Worked Example 14.4 Organic Reactions: Oxidation The starting material is a primary alcohol, so it will be converted first to an aldehyde and then to a carboxylic acid. To find the structures of these products, first redraw the structure of the starting alcohol to identify the hydrogen atoms on the hydroxyl-bearing carbon: Analysis What is the product of the following oxidation reaction? Solution Next, remove 2 hydrogens, one from the —OH group and one from the hydroxyl-bearing carbon. In their place, make a C=O double bond. This is the aldehyde product that forms initially. Finally, convert the aldehyde to a carboxylic acid by replacing the hydrogen in the —CH=O group with an —OH group.

© 2013 Pearson Education, Inc. Fundamentals of General, Organic, and Biological Chemistry, 7e John McMurry, David S. Ballantine, Carl A. Hoeger, Virginia E. Peterson Worked Example 14.5 Molecular Structures: Drawing Ethers and Alcohols First identify the parent compound, then add numbered substituents to appropriate carbons in the parent chain. Analysis Draw the structure for 3-methoxy-2-butanol. The parent compound is a 4-carbon chain with the —OH attached to C2. Solution The 3-methoxy substituent indicates that a methoxy group (—OCH 3 ) is attached to C3. Finally, add hydrogens until each carbon atom has a total of four bonds.