Nomenclature Review Activity The goal of this activity is to review the rules of IUPAC (International Union of Pure and Applied Chemistry) nomenclature encountered in Organic Chemistry I and II. Nomenclature of the following groups was discussed in Organic Chemistry I: alkanes (Ch. 4), alkyl halides (Ch. 7), alkenes (Ch. 7), alkynes (Ch. 9), and alcohols (Ch. 12). A short review is presented here. The following new groups will be studied in Organic Chemistry II: Ethers (Ch. 13), Benzene Derivatives (Ch. 17), Aldehydes (Ch. 19), Ketones (Ch. 19), Carboxylic Acid Derivatives (Ch. 20 - carboxylic acids, acid halides, anhydrides, esters, amides, nitriles), and Amines (Ch. 22). When naming compounds that contain multiple groups, a priority chart will become important. The following chart is not meant to be comprehensive but is meant to give you enough information to be able to solve the problems encountered in this activity. Part One: Review of IUPAC Nomenclature covered in Organic Chemistry I alkanes (Ch. 4), alkyl halides (Ch. 7), alkenes (Ch. 7), alkynes (Ch. 9), and alcohols (Ch. 12) Steps: 1. Identify and name the parent. 2. Identify and name the substituents. 3. Assign a locant to each substituent. 4. Assemble the substituents alphabetically. Here is a worked example of an alkene. Here is a worked example of a compound with more than one group. For more examples, refer to your textbook. Problems: Provide an IUPAC name for each of the following compounds. Part Two: IUPAC Nomenclature of Functional Groups covered in Organic Chemistry II I. Ethers (Ch. 13) Ethers can be named using two methods: Common Name and Systematic Name. 1. Common Name: A common name can be assigned if the oxygen atom is attached to two simple alkyl groups. The alkyl groups are listed in alphabetical order followed by the word “ether”. Identical alkyl groups are given the “di” prefix. 2. Systematic Name: The larger group is the parent and the smaller group is the alkoxy substituent. The parent is named as an alkane. Here is a worked example: Problems: Provide an IUPAC name for each of the following compounds. II. Benzene Derivatives (Ch. 17) Benzene is generally the parent name for monosubstituted derivatives: The following common names are accepted by IUPAC as parent names, and are frequently used. The common name for dimethyl benzene derivatives is xylene. Ortho, meta, and para are used for the location of substituents on disubstituted benzene rings. More examples: Another worked example: Problems: Provide an IUPAC name for each of the following compounds. III. Aldehydes and Ketones (Ch. 19) – For aldehydes, replace the “e” ending with an “-al”. For ketones, replace the “e” ending with an “-one” – The parent chain must include the carbonyl carbon. For ketones, the C=O carbon is given the lowest #, and can be expressed before the parent name or before the suffix. For aldehydes, the C=O carbon is always locant number 1. – Aldehydes have a higher priority than ketones. The keto group is called an “oxo” group when it is considered a substituent. Diketones are called “diones”. Problems: Provide an IUPAC name for each of the following compounds. IV. Carboxylic Acid Derivatives (Ch. 20 - carboxylic acids, acid halides, anhydrides, esters, amides, nitriles) – Monocarboxylic acids are named with the suffix “oic acid” – The carbon of the carboxylic acid moiety is assigned locant position 1 – There are many common names for carboxylic acids – Dicarboxylic acids are named with the suffix “dioic acid” – Some dicarboxylic acids have common names – To name an acid halide, replace - ic acid with - yl halide – Acid anhydrides are named by replacing “acid” with “anhydride” – Asymmetrical anhydrides are named by listing the acids alphabetically, followed by “anhydride” – Esters are named by naming the alkyl group attached to the oxygen followed by the carboxylic acid’s name with the suffix –ate – Amides are named by replacing the suffix -ic acid or -oic acid with –amide – If the nitrogen atom of the amide group bears alkyl substituents, their names are placed at the beginning of the name with N as their locant – Nitriles are named by replacing the suffix -ic acid or -oic acid with –onitrile Problems: Provide an IUPAC name for each of the following compounds. V. Amines (Ch. 22) IUPAC nomenclature allow for two different ways for naming 1° amines – Name the alkyl group ending in “yl” followed by the suffix “amine” – More complicated 1˚ amines are named as alkanamines. They are named the same as alcohols, but the suffix –amine is used instead of –ol – Use the term “amino” for the group as a substituent – If the amine is directly attached to an aromatic ring, the parent name is “aniline” There are multiple methods for naming 2˚ and 3˚ amines – Name the alkyl groups, followed by –amine suffix. Use “di” and “tri” if there are more than one of the same group. – Find the carbon parent chain, and use the suffix, amine. Smaller groups attached to the amine should be named as alkyl groups with the N-locant Problems: Provide an IUPAC name for each of the following compounds.
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