Advanced Level Organic Chemistry: Naming and structure of aromatic compounds
Part 7.1 What are they? How do you name them?
Notes on the Molecular Structure and Nomenclature -the naming of Aromatic Compounds - Arenes and substituted products
Doc Brown's Chemistry Advanced Level Pre-University Chemistry Revision Study Notes for UK KS5 A/AS GCE IB advanced level organic chemistry students US K12 grade 11 grade 12 organic chemistry Revising Advanced A Level Organic Chemistry Revision Notes
Sub-index for aromatic compound nomenclature
Introduction and then fast track to naming examples of
How do you name aromatic compounds e.g. arenes - aromatic hydrocarbons. Examples of displayed formula of aromatic compounds, graphic formula, molecular formula, skeletal formula, structural formula of aromatic hydrocarbons (arenes like benzene and methylbenzene), aromatic halides, phenols, aromatic aldehydes, aromatic ketones, aromatic carboxylic acids and derivatives, primary aromatic amine, secondary aromatic amines, tertiary aromatic amines, aromatic amides, diazonium Salts and azo dyes , nitro-aromatics, aromatic sulfonic/sulfonic acids . Please note that some 'old' names are quoted in () though their use should be avoided if possible, however, many are still used - just put one into Google! However, most names are based on the generic hexagonal 'benzene' ring with modifications to this based on the highest functional group attached to the ring (i.e. a ring substituent replacing a hydrogen)
Introduction to naming aromatic compounds
Aromatic/aryl Hydrocarbons (Arenes)
The simplest aromatic hydrocarbon is benzene,
The structures of benzene on the left and right are presented in 'old fashioned' Kekule style.
benzene molecular formula C6H6, skeletal formula , structural/displayed formula
methylbenzene (toluene) C7H8, C6H5CH3 , the simplest molecule where an alkyl groups has replaced a hydrogen atom in the benzene ring.
propylbenzene, C9H12 and isomeric 2-phenylpropane,1-methylethyl)benzene
phenylethene ('styrene'), C8H8, is usually named as a derivative of ethene, even though it is also technically an aromatic compound,
the C6H5- aromatic ring grouping is called a phenyl group when quoted as a substituent prefix.
So phenylethene is named as a derivative of ethene.
1,2-dimethylbenzene, C8H10, , 1,3-dimethylbenzene, 1,4-dimethylbenzene
Three positional structural isomers of C8H10 (once called xylenes, ortho, meta and para-xylene)
1-ethyl-2-methylbenzene, C9H12, and the two other positional structural isomers
1-ethyl-3-methylbenzene, C9H12, and
1,2-diethylbenzene, C10H14, , 1,3-diethylbenzene, 1,4-diethylbenzene
1,2-dipropylbenzene , 1,3-dipropylbenzene , 1,4-dipropylbenzene
1-methyl-2-propylbenzene, C10H14, and the two other positional structural isomers
4-ethyl-1,2-dimethylbenzene, C10H14, (uses lower numbers than 1-...-3,4-...)
Examples of fused ring systems of arene hydrocarbon compounds - polynuclear aromatic ring compounds
Two aromatic rings that share a pair of carbon atoms are said to be fused.
OLYMPICENE molecular structure, shape and bond angles
Olympicene (caught my imagination in 2012!), C19H12, (Mr = 240, bpt 512oC), was one of the latest arrivals of a polynuclear aromatic hydrocarbon compound from synthetic organic chemistry in 2011. It was conceived and synthesised by a British research group for the London 2012 Olympic Games. The Olympicene molecule consists of five 'fused' hexagonal rings of carbon atoms (the official Olympic symbol consists of five 'interlocking rings' - can't show due to copyright law!).
Halo-arenes - aryl/aromatic 'halides'
chlorobenzene, C6H5Cl, and
1,2 or 1,3 or 1,4-dichlorobenzene, C6H4Cl2, ,,
C7H7Cl, (chloromethyl)benzene (benzyl chloride). It is not a true aryl halogen compound, the halogen atom is in a non-aromatic side chain, so it is a primary aliphatic halogenoalkane.
Three positional structural isomers of C7H7Cl
1-chloro-2-methylbenzene, 1-chloro-3-methylbenzene and 1-chloro-4-methylbenzene,or 1-chloro-2-methylbenzene, 1-chloro-3-methylbenzene and 1-chloro-4-methylbenzene (old names 0-chlorotoluene, m-chlorotoluene and p-chlorotoluene). These are true aryl halides with the halogen attached directly to the benzene ring and they are isomeric with (chloromethyl)benzene above.
C7H6Cl2, dichloro-2,3-methylbenzene, dichloro-2,4-methylbenzene, dichloro-2,5-methylbenzene
or 1,2-dichloro-3-methylbenzene, 2,4-dichloro-1-methylbenzene and 2,5-dichloro-1-methylbenzene
dichloro-2,6-methylbenzene, dichloro-3,4-methylbenzene, dichloro-3,5-methylbenzene,
or 1,3-dichloro-2-methylbenzene, 1,2-dichloro-4-methylbenzene and 3,5-dichloro-1-methylbenzene (1,3-dichloro-5-methylbenzene)
C8H9Cl, 1-chloro-2,4-dimethylbenzene , 1-chloro-2,3-dimethylbenzene,
1-chloro-3,4-dimethylbenzene (4-chloro-1,2-dimethylbenzene), 2-chloro-1,3-dimethylbenzene
1-chloro-2,4-dimethylbenzene, 1-chloro-3,5-dimethylbenzene, 2-chloro-1,4-dimethylbenzene
Phenols - aryl/aromatic hydroxy compounds - aromatic alcohols
C6H5OCl, 2-chlorophenol (o-chlorophenol), 3-chlorophenol (m-chlorophenol),
C7H8O, 2-methylphenol (o-methylphenol, ortho-cresol)
If the OH is not attached to a benzene ring you get an aliphatic alcohol which is isomeric with a phenols or an ether.
C6H7NO, 2-aminophenol, 3-aminophenol, 4-aminophenol
2-nitrophenol, 3-nitrophenol, 4-nitrophenol
These molecules can also be called: 2-hydroxynitrobenzene, 3-hydroxynitrobenzene and 4-hydroxynitrobenzene
These molecules have two functional groups: phenol and primary aromatic amine and phenol and aromatic-nitro functional groups.
C7H6O3, 3-hydroxybenzoic acid and 2-hydroxybenzoic acid
C6H6O2, or 1,4-dihydroxybenzene (benzene-1,4-diol, 1,4-benzenediol, 'quinol')
which is oxidised to
C6H4O2, or 2,5-cyclohexadiene-1,4-dione (cycohexa-2,5-diene-1,4-dione, 'p-quinone')
C8H10O,1-phenylethanol, which is isomeric with the ether
C8H10O, ethoxybenzene (phenetole) and the ethylphenols or dimethylphenols.
Aromatic aldehydes and ketones
The 'aldehyde' part of the name is usually the suffix in an aromatic aldehyde's name (as in aliphatic aldehydes).
True aromatic aldehydes, R-CHO, have the aldehyde group -CHO directly attached to the ring e.g.
C7H6O, orbenzaldehyde, and
The 'ketone' part of the name, one, is usually the suffix in an aromatic ketone's name (as in aliphatic ketones).
Ketones, R2C=O, R = alkyl or aryl. aromatic ketones are often 'mixed' aliphatic-aromatic in the sense that one R group is alkyl and the other R group is aryl e.g.
Aromatic carboxylic acids and their derivatives
Note: quite a few of the 'old' names are still used and accepted
The name ends in ...carboxylic acid or ...oic acid, in salts and esters the suffix is ...oate
The derivative names are similar for aliphatic carboxylic acids and their derivatives e.g.
C7H6O2, , , , , benenecarboxylic acid, benzoic acid
C7H5OCl, , , , , benzenecarbonyl chloride, benzoyl chloride
C7H7ON, , , , , benzenecarboxamide, benzamide
C8H8O2, , , , , methyl benzenecarboxylate, methyl benzoate
C8H8O3, methyl 2-hydroxybenzoate
C9H10O2, , , , ethyl benzenecarboxylate, ethyl benzoate
C10H12O2, , , , propyl benzenecarboxylate, propyl benzoate
C7H5O3, 2-, 3- or 4-hydroxybenzenecarboxylic acid, 2-, 3- or 4-hydroxybenzoic acid
C7H5ClO2 , 2-, 3- and 4-chlorobenzoic acid
5g. C7H5NO3 , 2-, 3- and 4-nitrobenzoic acid
5h. C7H7NO2 , 2-, 3- and 4-aminobenzoic acid
5i. 2-methylbenzoic acid , 3-methylbenzoic acid , 4-methybenzoic acid
5j. C8H6O4, benzene-1,2-dicarboxylic acid (or -1,3- or -1,4-)
(primary, 2 H's and only one R group attached to the N of the amine group, R-NH2 where R = alkyl or aryl)
The amino (prefix) or amine (suffix) group is directly attached to the aromatic benzene ring
e.g. C6H7N, the simplest is C6H5NH2, phenylamine (technically it is aminobenzene, but this name is rarely used.
C6H6NCl, 2- or 3- or 4-chlorophenylamine
C6H8N2, 1,3-diaminobenzene, ,
C7H9N, 2-methylphenylamine, methyl-2-phenylamine, 1-amino-2-methylbenzene
This is isomeric with benzylamine which is a primary aliphatic amine because the amine group is not directly attached to the ring.
Secondary AROMATIC amines
(secondary, one H and two R groups attached to the N of the amine group, R2NH where R = alkyl or aryl)
C7H9N, N-methylphenylamine, and C8H11N, N-ethylphenylamine
and C10H11N, diphenylamine
Aromatic TERTIARY AMINES and quaternary ammonium salts
(tertiary, no H and three R groups attached to the N of the amine group, R3N where R = alkyl or aryl)
N,N-dimethylphenylamine, C8H11N, , N,N-diethylphenylamineC10H15N,
The quaternary ammonium salts would have the formulae [C6H5NH(CH3)2]+ and [C6H5NH(CH2CH3)2]+
and C18H15N, triphenylamine
The quaternary ammonium salt would have the formula [(C6H5)3NH]+
Aromatic PRIMARY ACID AMIDES
(primary, no alkyl/aryl R group and 2H's on the N of amide group)
The simplest primary aromatic acid amide is
benzamide or benzenecarboxamide, C7H7NO,, ,
Aromatic SECONDARY ACID AMIDES
(secondary, 1 alkyl/aryl R group and 1H on the N of amide group)
N-phenylethanamide, C8H9NO, (this is really a phenyl derivative of the aliphatic amide, ethanamide)
N-methylbenzamide, C8H9NO, , and
N-phenylbenzamide, C13H11NO, (both true secondary aromatic amide)
Are secondary amides formed in a condensation polymerisation reaction between a carboxylic acid and an amine.
Water is eliminated between the two 'monomers' to give the secondary, polyamide (polymer) linkage ...
-COOH + H2N- ==> -CO-NH- + H2O
KEVLAR is an aromatic polyamide formed from benzene-1,4-dicarboxylic acid and 1,4-diaminobenzene
Aromatic TERTIARY ACID AMIDES
Tertiary amides would have no H and 2 aryl/alkyl groups on N of amide group.
DIAZONIUM SALTS and AZO DYES:
Diazonium salts are formed when primary aromatic amines reaction with nitrous acid
e.g. C6H5NH2(aq) + HNO2(aq) + H+(aq) ==> C6H5N2+(aq) + 2H2O(l)
The diazonium cation has a nitrogen-nitrogen triple bond system directly attached to the benzene ring e.g.
(1) from phenylamine
(2) from 4-methylphenylamine
(3) from 2-aminobenzoic acid.
In alkaline solution these diazonium salts couple with phenols and aromatic amines to form azo dyes.
These dyes have benzene rings linked with an azo -N=N- bond system e.g.
reacting (1) with phenol gives
reacting (1) with phenylamine gives
reacting (2) with phenol gives
reacting (2) with phenylamine gives
These have the nitro -NO2 group directly attached to the ring. On reduction they form primary aromatic amines.
nitrobenzene, C6H5NO2, and , C6H4N2O4, 1,3-dinitrobenzene,
3 isomers of C6H4NO2Cl, 1-chloro-2-nitrobenzene , 1-chloro-3-nitrobenzene , 1-chloro-4-nitrobenzene
C7H7NO2, methyl-2-nitrobenzene, or 1-methyl-2-nitrobenzene (o-nitrotoluene, ortho nitrotoluene)
and the two other positional structural isomers
Aromatic Sulfonic Acids (sulfonic acids)
These molecules have a strongly mono-basic acidic group -SO2OH directly attached to the benzene ring e.g.
benzenesulfonic acid, C6H6SO3, C6H5SO3H, C6H5SO2OH, (benzenesulfonic acid)
2-, 3- or 4-methylbenzenesulfonic acid, C7H8SO3, CH3C6H5SO2OH,, ,
KEYWORDS: fast track to nomenclature examples of ... Hydrocarbons (Arenes) ... Halo-Aromatics ... Phenols ... Aldehydes and Ketones ... Carboxylic Acids and Derivatives ... Amines (prim/sec/tert) ... Amides ... Diazonium Salts and azo dyes ... Nitro-Aromatics ... Sulfonic Acids
formula keywords: how to name naming nomenclature empirical molecular formula graphic formula displayed formula skeletal formula structural isomers isomerism for aromatics aromatic compounds Hydrocarbons arenes) ... Halo-Aromatics ... Phenols ... Aldehydes and Ketones ... Carboxylic Acids and Derivatives ... primary prim secondary sec tertiary tert Amines (prim/sec/tert) ... Amides ... Diazonium Salts and azo dyes ... Nitro-Aromatics ... Sulfonic Acids C6H6 C7H8 C6H5CH3 C8H10 CH3C6H4CH3 C6H5CH2CH3 C8H18 C6H5CH=CH2 C9H12 C10H14 C11H16 C6H5Cl C6H4Cl2 ClC6H4Cl C7H7Cl C6H5CH2Cl CH3C6H4Cl C7H6Cl2 C8H9Cl C6H6O C6H5OH C6H5OCl C6H5ClO ClC6H4OH C7H8O CH3C6H4OH HOC6H4NH2 NH2C6H4OH H2NC6H4OH C6H7ON C6H7NO C7H6O3 HOC6H4COOH C7H6OCl2 C7H6Cl2O C6H6O2 HOC6H4OH C6H4O2 C6H5CH2OH C6H5OCH3 C8H10O C6H5OCH2CH3 C6H5OCH2CH7H6O2 C6H5COOH C7H6O C6H5CHO C7H6O2 HOC6H4CHO C8H8O C6H5COOCH3 C8H8O2 C13H10O C7H6O2 C6H5COOH C7H5OCl C7H5ClO C68H11N C6H5NHCH2CH3 C6H5COCl C7H7ON C7H7NO C6H5CONH2 C8H8O2 C6H5COOCH3 C8H8O3 C9H10O2 C6H5COOCH2CH3 C9H10O2 C10H12O2 C6H5COOCH2CH2CH3 C7H6O3 HOC6H4COOH C7H5ClO2 C7H5O2Cl ClC6H4COOH C8H6O4 HOOCC6H6COOH C6H7N C6H5NH2 C6H6NCl C6H6ClN C6H8N2 H2NC6H4NH2 NH2C6H4NH2 C7H9N CH3C6H4NH2 C6H5CH2NH2 C6H5NHCH3 C8H11N C6H5NHCH2CH3 C10H11N C6H5NHC6H5 C9H11N C10H15N C18H15N C7H7NO C7H7ON C6H5CONH2 C8H9NO C8H9ON CH3CONHC6H5 C6H5CONHCH3 C13H11NO C13H11ON C6H5CONHC6H5 C9H11NO C9H11ON C6H5NO2 C6H5ON2 C6H4N2O4 C6H4O4N2 C6H4NO2Cl C6H4O2NCl C6H4O2ClN C6H4ClNO2 C6H4ClO2N C6H4NClO2 ClC6H4NO2 O2NC6H4Cl NO2C6H4Cl C7H7NO2 C7H7O2N CH3C6H4NO2 O2NC6H4CH3 NO2C6H4CH3 C7H5NO3 O2NC6H4COOH NO2C6H4COOH C6H6O3S C6H6SO3 C6H5SO3H C6H5SO2OH C7H8SO3 CH3C6H4SO2OH C10H8 C14H10 C19H12 These detailed notes on the structure and naming of aromatic compounds include the general formula of aromatic compound molecules, empirical formula of aromatic compound molecules, structural formula of aromatic compound molecules, skeletal formula of aromatic compound molecules, displayed formula of aromatic compound molecules, shapes of aromatic compound molecules, isomers of aromatic compound molecules IUPAC rules for aromatic nomenclature. Students should be able to draw structural formula of aromatic, displayed and skeletal formulas for aromatic organic compounds apply IUPAC rules for nomenclature to name aromatic acid organic compounds including chains and rings and be able to apply IUPAC rules for nomenclature to draw the structural, displayed or skeletal structure of aromatic organic compounds from the aromatic IUPAC name from the homologous series of aromatics
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