Aromatic Nomenclature

Naming substituted benzenes

Monosubstituted Benzenes
Most monosubstituted aromatics are named using -benzene as the parent name preceded by the substituent name (as a prefix; all one word):
fluoro
F

nitro
NO2

ethyl
CH2CH3

fluorobenzene

nitrobenzene

ethylbenzene

Alkyl-substituted Benzenes
Alkyl substituted benzenes are named according to the length of the carbon chain of the alkyl group. With six carbons or fewer in the alkyl chain, they are named as alkylbenzene. e.g., propylbenzene:
CH2CH2CH3

Alkyl-substituted Benzenes
With more than six carbons in the alkyl chain, they are named as a phenylalkane, where the benzene ring is named as a substituent (phenyl) on the alkane chain e.g., 4-phenylnonane
CH2CH2CH3 CHCH2CH2CH2CH2CH3 =

CH 3CH 2CH 2

CHCH 2CH 2CH 2CH 2CH 3

CH3CH2CH2CHCH2CH2CH2CH2CH3

4-phenylnonane

Common Names of Subs. Benzenes

There are a number of nonsystematic (common) names commonly used for certain monosubstituted benzenes (see next slide) These ten common names should be memorized. These common names are used as base names when naming more their more highly substituted derivatives. Examples of these will be given later.

Common Names of Subs. Benzenes

CH3 OH NH2 tolue ne OCH3 phenol H C CH2 O C CH3 aniline

O C H

anisole

O C OH

styre ne

be nzalde hyde C N

be nzoic acid

CH3 CHCH3

ace tophe none

be nzonitrile

cume ne

The Benzyl Group

The benzyl group is a common name for a methyl substituted benzene (toluene) having substitution for one of the hydrogens on the methyl group.

CH2

CH2Br

CH2OH

CH 2Br

the benzyl group

benzyl bromide

benzyl alcohol

Disubstituted Benzenes
Disubstituted benzenes can be named in one of two ways. Each method describes the relative positions of the two groups on the benzene ring. Systematic numbering of the aromatic ring. Using the prefixes ortho-, meta-, or para-. When numbering the ring carbons, carbon # 1 is always a substituted carbon. The substituents are listed alphabetically.

Disubstituted Benzenes
ortho- (abbreviated o- ) = 1,2-disubstituted (two groups on adjacent carbons on the ring)
F F CH2CH3 Br o-difluorobe nze ne or 1,2-difluorobe nze ne o-bromoe thylbe nze ne or 1-bromo-2-e thylbe nze ne

Disubstituted Benzenes
meta- (abbreviated m- ) = 1,3-disubstituted (two groups having one unsubstituted carbon between them)
Br Br Br NO2

m-dibromobe nze ne or 1,3-dibromobe nze ne

m-bromonitrobe nze ne or 1-bromo-3-nitrobe nze ne

Disubstituted Benzenes
para- (abbreviated p- ) = 1,4-disubstituted (two groups on opposite sides of the ring)
Br Cl Cl p-dichlorobe nze ne or 1,4-dichlorobe nze ne Cl p-bromochlorobe nze ne or 1-bromo-4-chlorobe nze ne

Disubstituted Benzenes
When one of the substituents changes the base name, either o-, m-, and p- or numbers may be used to indicate the position of the other substituent. Carbon # 1 is always the carbon bearing the substituent that changes the base name.
Br

OH

3 2

1 2 Cl

NH2

p-bromoaniline or 4-bromoaniline

o-chlorophenol or 2-chlorophenol

Common Names of Disubs. Benzenes

There are a few nonsystematic (common) names for disubstituted benzenes that you should be familiar with:
CH3 CH3 CH3 m-xyle ne CH3 OH CH3 OH m-cre sol OH p-cre sol CH3 CH3 CH3 p-xyle ne

o-xyle ne CH3

o-cre sol

Polysubstituted Benzenes
Polysubstituted benzenes must be named by numbering the position of each substituent on the ring (with more than two substituents, o-, m-, and pcan NOT be used.) The numbering is carried out to give the substituents the lowest possible numbers. Carbon #1 always has a substituent. CH2CH3 List the substitutents 2 F 1 3 alphabetically with 4 their appropriate #s. NO2
2-ethyl-1-fluoro-4-nitrobenzene

Polysubstituted Aromatics having a Common base name

Common names of the monosubstituted benzenes are used as parent names for polysubstituted aromatics when one of the substituents changes the base name. For such rings with common names, the carbon bearing the substituent responsible for the common name is always carbon #1. toluene CH3 The substitutents are 1 Cl chloro listed in alphabetical 2 order. bromo
4 5-bromo-2-chlorotoluene
Br 5

Polysubstituted Benzenes
Br OH

Cl

2
Br 5

2 CH2CH3

3 4

NO2

4-bromo-2-ethyl-1-nitrobenzene

5-bromo-2-chlorophenol

Polysubstituted Benzenes
Br Br

2 3
O2N 4

1 CH3 6 6 Cl
O2N 5

1 2 CH2CH3 3 4
Cl

2-bromo-6-chloro-4-nitrotoluene

1-bromo-3-chloro-2-ethyl-5-nitrobenzene

Polycyclic Aromatic Hydrocarbons (PAH)

naphthalene

anthracene phenanthrene

pyrene

benzo [a] pyrene

Metabolic byproducts of benzo [a] pyrene react with DNA to form adducts, leading to carcinogenesis (cancer).