CHAPTER 13: AROMATIC COMPOUNDS

1. Give IUPAC names for the following compounds (one substituent)

O F NH 2
C OH

benzoic acid florobenzene aniline(aminobenzene)

OH Br C HO

phenol(hydroxybenzene bromobenzene benzaldehyde

NO2 C H3 Cl

nitrobenzene toluene(methylbenzene) clorobenzene

O C(CH
CH( C H3)3)3
CH2CH3
C C H3

tert-butylbenzene
ethylbenzene acetophenone
(1,1-dimethylethyl)benzene
 2. Ortho- / meta- / para- disubstituted (two substituents)

Cl
Cl Cl
Cl

Cl Cl
o-dichlorobenzene m-dichlorobenzene p-dichlorobenzene

Br
C H3 NO2
O2N

C H3 Br
m-dimethylbenzene p-dibromobenzene o-dinitrobenzene

3. Names based on priority (2 different substituents) :

Cl NO2
NO2
Br
NH2 NH2
1-chloro-2-nitrobenzene 2-bromoaniline 2-nitroaniline
(o-bromoaniline) (o-nitroaniline)

Br COOH
Cl CH2CH2CH3

Cl Cl
1-bromo-4-chlorobenzene 1-chloro-3-propylbenzene 3-chlorobenzoic acid
 C OOH OH
CH3

OH Br C H2C H 3
4-bromotoluene
3-hydroxybenzoic acid 3-ethylhydroxybenzene
(3-ethylphenol)

O
CHO
C OH

NH2 Br
3-aminobenzoic acid 4-bromobenzaldehyde 3-methylphenol

4. Give IUPAC names for the following compounds (phenyl)

CH2 CH2 CH3

CH3 CH CH
C H3 C H3 HC C
C H3 C C H 2 C H C H2
C H3

(1-methylpentyl)benzene (1,1,3-trimethylpentyl)benzene phenylethene

H2C CH2 CH2OH C H3 C C H C H3

OH
3-phenyl-1-propanol 2-phenylcyclopropanol
2-phenyl-2-butene
5. Draw a structure corresponding to the following IUPAC nameclature:

(a) 3-fluoroaniline (b) 2-phenyl-2-pentene

(c) 3-phenylcyclooctene (d) o-chlorophenol

(e) 4-isopropylnitrobenzene (f) 2,4-dimethylphenol

(g) m-bromotoluene (h) 2-chloro-2-phenylcyclopentanol

(i) 3-phenyl-2-butanol (j) p-nitroaniline