Sample Problem 13.1 Naming Alcohols Give the IUPAC name for the following: Solution Step Name the longest carbon chain attached to the —OH group by replacing the e in the corresponding alkane name with ol To name the alcohol, the e in alkane name pentane is replaced by ol Step Number the chain starting at the end nearer to the —OH group This carbon chain is numbered from right to left to give the position of the —OH group as carbon 2, which is shown as a prefix in the name 2-pentanol General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Sample Problem 13.1 Naming Alcohols Continued Step Give the location and name of each substituent relative to the —OH group Study Check 13.1 Give the IUPAC name for the following: Answer 3-chloro-1-butanol General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Sample Problem 13.2 Naming Phenols Give the IUPAC and common names for the following: Solution Step Name an aromatic alcohol as a phenol The compound is a phenol because it contains an —OH group attached to a benzene ring General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Sample Problem 13.2 Naming Phenols Continued Step Number the chain starting at the end nearer to the —OH group For a phenol, the carbon atom attached to the —OH group is carbon Step Give the location and name for each substituent relative to the —OH group For the common name, use the prefix ortho (o-) General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Sample Problem 13.2 Naming Phenols Continued Study Check 13.2 Give the IUPAC and common names for the following: Answer 4-methylphenol (p-methylphenol; p-cresol) General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Sample Problem 13.3 Naming Ethers Give the IUPAC name for the following: CH3—CH2—O—CH2—CH2—CH2—CH3 Solution Step Write the alkane name of the longer carbon chain Step Name the oxygen and smaller alkyl group as an alkoxy group Step Number the longer carbon chain from the end nearer the alkoxy group and give its location General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Sample Problem 13.3 Naming Ethers Continued Study Check 13.3 What is the IUPAC name of methyl phenyl ether? Answer methoxybenzene General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Sample Problem 13.4 Classifying Alcohols Classify each of the following alcohols as primary (1°), secondary (2°), or tertiary (3°): a CH3—CH2—CH2—OH b Solution a The carbon atom bonded to the —OH group is attached to one alkyl group, which makes this a primary (1°) alcohol b The carbon atom bonded to the —OH group is attached to three alkyl groups, which makes this a tertiary (3°) alcohol Study Check 13.4 Classify the following alcohol as primary (1°), secondary (2°), or tertiary (3°): Answer secondary (2°) General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Sample Problem 13.5 Dehydration of Alcohols Draw the condensed structural formula for the major alkene produced by the dehydration of each of the following alcohols: a b Solution a The 1-butanol loses —OH from carbon and H— from carbon to form 1-butene This is the only possible product CH3—CH2—CH b CH2 For the dehydration of an asymmetrical alcohol, we use Saytzeff’s rule to remove —OH from carbon and H— from carbon 3, which has the smaller number of H atoms The major product is 2-pentene CH3—CH—CH—CH2 CH3 Study Check 13.5 What is the name of the alkene produced by the dehydration of cyclopentanol? Answer cyclopentene General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Sample Problem 13.6 Oxidation of Alcohols Draw the condensed or line-angle structural formula for the aldehyde or ketone formed by the oxidation of each of the following: a b Solution a This is a secondary (2°) alcohol, which oxidizes to a ketone b This is a primary (1°) alcohol, which oxidizes to an aldehyde Study Check 13.6 Draw the condensed structural formula for the product formed by the oxidation of 2-pentanol General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc Sample Problem 13.6 Oxidation of Alcohols Continued Answer General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake © 2016 Pearson Education, Inc ... the location and name for each substituent relative to the —OH group For the common name, use the prefix ortho (o-) General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake... 13.2 Give the IUPAC and common names for the following: Answer 4-methylphenol (p-methylphenol; p-cresol) General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C Timberlake... oxygen and smaller alkyl group as an alkoxy group Step Number the longer carbon chain from the end nearer the alkoxy group and give its location General, Organic, and Biological Chemistry: Structures