IUPAC Rules for Naming Organic Compounds (Biochemistry 2210) – Part II I. Amines (6) 1. IUPAC names for aliphatic amines use the same system as used for alcohols. a. Drop the final “‐e” of the parent alkane and replace it by “–amine”. 2. Use a number to locate the amino group on the parent chain. Number the parent alkane so that the amino group has the lowest number. 3. Name and number each substituent on the parent chain and use a hyphen to connect the number to the name. List them in alphabetical order. 4. IUPAC nomenclature retains the common name aniline for C6H5NH2, the simplest aromatic amine. 5. Name simple derivatives of aniline by using numbers to locate substituents relative to the amino group or, alternatively, use the prefixes ortho (o), meta (m), and para (p) as was done for benzene derivatives. 6. Name unsymmetrical secondary and ter tiary amines as N‐substituted primary amines. a. Take the largest group bonded to nitrogen as the parent amine. b. Name the smaller group(s) bonded to nitrogen, and show their location on nitrogen by using the prefix N‐. Common names: 1. For most aliphatic amines, list the common alkyl groups bonded to nitrogen in alphabetical order in one word ending in the suffix “‐amine”. 2. For amine salts, replace the ending “‐amine” (or “aniline” or “pyridine” or the like) by “‐ammonium” (or “aniliniu m” or “pyridinium” or the like) and add the name of the anion J. Aldehydes (3): 1. To name an aldehyde, change the suffix “‐e” of the parent alkane to “‐al”. 2. The carbonyl carbon for an aldehyde on the parent alkane is always given the number “1”. 3. For unsaturated aldehydes, indicate the presence of a carbon‐carbon double bond by changing the ending of the parent alkene from “‐ene” to “‐enal”. a. Numbering the carbon chain begins with the aldehyde carbonyl carbon. b. Show the location of the carbon‐carbon double bond by the number of its first carbon. K. Ketones (4): 1. To name a ketone, the parent alkane is the longest chain that contains the carbonyl group. 2. Indicate the presence of the carbonyl group by changing the “‐e” of the parent alkane to “‐one”. 3. Number the parent chain from the dire ction that gives the carbonyl carbon the smaller number 4. To name an aldehyde or ketone that also contains a hydroxyl or amino group: a. Number the parent chain to give the carbonyl carbon the lower number. b. Hydroxyl and amino substituents are numbered and alphabetized along with other substituents on the parent alkane chain Common names 1. The common name for a ketone is derived from the name of each common alkyl or aryl group bonded to the carbonyl carbon as a separate word, followed by the word "ke tone”. 2. Alkyl or aryl groups are generally listed in order of increasing molecular weight. L. Carboxylic acids (3): 1. For an acyclic carboxylic acid, choose the longest carbon chain tha t contains the carboxyl group as the parent alkane. Drop the final “‐e” from the name of the parent alkane and replace it by “‐oic acid”. 2. Number the chain beginning with the carbon of the carboxyl group which must always be “1”. 3. To name a dicarboxylic acid, add the suffix “‐dioic acid” to the name of the parent alkane that contains both carboxyl groups; thus, “‐ane” becomes –“anedioic acid”. Again, the numbers of the carboxyl carbons are not indicated because they can be only at the ends of the chain (Note: Common naming of carboxylic acids will not be required in this course unless otherwise specified.) M. Anhydrides (3): 1. To name an anhydride, dro p the word "acid" from the name of the carboxylic acid from which the anhydride is derived and add the word "anhydride”. 2. For mixed anhydrides, name the parent carboxylic acids involved alphabetically, again by adding the word “anhydride” after. N. Esters (1): 1. IUPAC names of esters are derived from the names of the parent carboxylic acids. Name the alkyl or aryl group bonded to oxygen first, followed by the name of the acid; replace the suffix “‐ic acid” by “‐ate”. (Note: We will not be systematically naming lactones in this course.) O. Amides (3): 1. IUPAC names of amides are derived by dropping the suffix “‐oic acid” from the IUPAC name of the parent acid and add “‐amide”. Example: Ethanamide 2. Common names of amides are derived by dropping the suffix “‐ic acid” from its common name, and add “‐amide”. Example: Acetamide (Acetamide = Ethanamide) 3. If the amide nitrogen is also bonded to an alkyl or aryl group, name the group and show its location on nitrogen by “N‐“; two alkyl or aryl groups by “N,N‐di‐“. (Note: We will not be systematically naming lactams in this course.)