Important Rules for Naming Organic Compounds: NITIN VERMA
1) Identify the longest carbon chain in the molecule.
2) If there’s more than one carbon chain, the chain with greater number of substituents is selected as the parent chain. 3) The chain is numbered in such a way that the substituents get the lowest possible positions. 4) In case of equivalent positions, the substituent that comes first alphabetically is given the lower number. 5) In case of complex substituents, the C of the substituent joined to the parent chain is numbered 1. 6) Complex substituents are put in small brackets. 7) If a cycloalkane has two substituents, the numbering is done so as to give lower number to the substituent that comes first alphabetically. 8) If a cycloalkane has more than two substituents, the ring is numbered in such a way that the substituents get the lowest possible positions. GOC BY Important Rules for Naming Organic Compounds: NITIN VERMA
9) If a compound has one functional group, the longest carbon chain is selected such that it includes the functional group at the lowest possible position. 10) A functional group is written as suffix to the word root (parent alkane). If the suffix begins with a vowel, the ending –e of the alkane is dropped. 11) If a compound contains more than one functional group of the same type (e.g., 2 –OH groups), the ending –e of the alkane is retained. 12) If a compound contains two or more functional groups of different types (e.g., –OH and –COOH), the functional group that comes first in the priority order given below is selected as the principal functional group; it is written as suffix to the word root. The other functional group(s) is (are) written as prefix(es). Priority in decreasing order: –COOH, –SO3H, (RCO)2O –COOR (R = alkyl group), COCl, –CONH2, –CN, –HC=O, >C=O, –OH, –NH2, >C=C<, –C≡C– GOC BY Important Rules for Naming Organic Compounds: NITIN VERMA
13) If the carbon atom of a functional group is not included in the parent chain, the prefix “carb” is used for the functional group suffix. —CHO : carbaldehyde —COOH : carboxylic acid —CONH2 : carboxamide —COCl : carbonyl chloride —CN : carbonitrile 14) The –R, C6H5–, halogens (F, Cl, Br, I), –NO2, alkoxy (–OR), etc. are always written as prefixes. 15) In case a compound contains >C=C< and/or –C≡C– bonds, the chain is numbered to give these bonds lowest possible positions. 16) In case of equivalent positions, >C=C< is given lower number than –C≡C– bond. 17) If a compound contains more than one carbon–carbon multiple bonds of the same type, the word root alka is used (and NOT alk). GOC BY Important Rules for Naming Organic Compounds: NITIN VERMA
18) In case of substituted benzenes, if the side chain contains more than 6 carbon atoms or functional group(s), the side chain is taken as the parent chain. Otherwise, benzene is treated as the parent chain. 19) If benzene contains any functional group, it is given priority while numbering the ring carbon atoms. 20) In case of only substituents, i.e., no functional group, the lowest locants rule is obeyed. 21) In bicyclo compounds, the numbering of parent chain is started at a bridge-head carbon and then the bridges are numbered from longest to the shortest bridge. The name is written as “bicyclo(x.y.z)alkane”, where x, y, and z are the number of atoms in the bridges, respectively, in the decreasing order. 22) In spiro compounds, C1 next to the bridge-head carbon in the smaller ring is chosen for numbering and completed on the larger ring. The name is written as “spiro(x.y)alkane, where x and y are the number of atoms in the rings, respectively, in the increasing order. GOC BY Nomenclature of Alkanes: NITIN VERMA
• di, tri, tetra, sec, and tert are ignored in
alphabetizing, whereas iso, neo, and cyclo are NOT ignored in alphabetizing. GOC BY Some Common Alkyl Groups: NITIN VERMA
• n–Alkyl: all carbon atoms are in a straight chain.
Examples: n–butyl, n–pentyl, etc.
• sec–Alkyl: bonding occurs through a secondary (2°) carbon atom.
Examples: sec–butyl (the only sec– group)
• tert–Alkyl: bonding occurs through a tertiary (3°) carbon atom.
Examples: tert–butyl and tert–pentyl
• Neoalkyl: a structural unit having a carbon atom surrounded by four other carbon atoms. Examples: neopentyl and neohexyl
• Isoalkyl: a structural unit having (CH3)2CH— group at one end of the chain. Examples: isopropyl, isobutyl, etc. GOC BY Some Common Alkyl Groups: NITIN VERMA
• Vinyl: CH2=CH– (vinylic C is sp2 hybridized carbon atom)
• Allyl: CH2=CH–CH2– (allylic C is sp3 hybridized carbon atom joined to a sp2 hybridized carbon atom)
• Benzyl: PhCH2– (benzylic C is a sp3 hybridized carbon atom joined to benzene ring)
Note: allylic and benzylic compounds can be 1°, 2° and 3 in nature.
Table 12.4 Some Functional Groups and Classes of Organic Compounds GOC BY NITIN VERMA
