Nomenclature of

Hydrocarbons
1. Introduction to Alkanes &
Cycloalkanes
 Alkanes and cycloalkanes are
hydrocarbons in which all the carbon-
carbon (C–C) bonds are single bonds

 Hydrocarbons that contain

C═C: Alkenes
Hydrocarbons that contain
C≡C: Alkynes
Ch. 4 - 2
 Alkanes: CnH2n+2
5 3 1
e.g.
6 4 2
hexane (C6H14)

 Cycloalkanes: CnH2n

e.g.
cyclohexane (C6H12)

Ch. 4 - 3
1A. Sources of Alkanes: Petroleum

 Petroleum is the primary source of

alkanes. It is a complex mixture of
mostly alkanes and aromatic
hydrocarbons with small amounts of
oxygen-, nitrogen-, and sulfur-
containing compounds

Ch. 4 - 4
 Petroleum refining

● Distillation is the first step in

refining petroleum. Its components
are separated based on different
volatility

● More than 500 different compounds

are contained in petroleum
distillates boiling below 200oC

Ch. 4 - 5
 Petroleum refining (Cont’d)

● The fractions taken contain a

mixture of alkanes of similar boiling
points

● Mixture of alkanes can be used as

fuels, solvents, and lubricants

Ch. 4 - 6
 Gasoline
● The demand of gasoline is much
greater than that supplied by the
gasoline fraction of petroleum
● Converting hydrocarbons from other
fractions of petroleum into gasoline
by “catalytic cracking”

mixture of alkanes catalysts highly branched

(C12 and higher) ~ 500oC hydrocarbons
(C5 - C10)
Ch. 4 - 7
 Gasoline (Cont’d)
CH3 CH3
CH3 C CH2 C CH3
CH3 H
2,2,4-Trimethylpentane (isooctane)
(C12H18)
● Isooctane burns very smoothly
(without knocking) in internal
combustion engines and is used as
one of the standards by which the
octane rating of gasoline is
established Ch. 4 - 8
 Gasoline (Cont’d)

isooctane heptane

"octane
rating" 100 0

● e.g. a gasoline of a mixture:

87% isooctane and 13% heptane
 Rated as 87-octane gasoline

Ch. 4 - 9
 Typical Fractions Obtained by
Distillation of Petroleum
Boiling Range of # of Carbon Use
Fraction (oC) Atoms per
Molecule
Below 20 C1 – C4 Natural gas, bottled
gas, petrochemicals
20 – 60 C5 – C6 Petroleum ether,
solvents
60 – 100 C6 – C7 Ligroin, solvents

40 – 200 C5 – C10 Gasoline (straight-

run gasoline)
175 – 325 C12 – C18 Kerosene and jet
fuel
Ch. 4 - 10
 Typical Fractions Obtained by
Distillation of Petroleum
(Cont’d)
Boiling Range of # of Carbon Use
Fraction (oC) Atoms per
Molecule
250 – 400 C12 and higher Gas oil, fuel oil, and
diesel oil
Nonvolatile liquids C20 and higher Refined mineral oil,
lubricating oil, and
grease
Nonvolatile solids C20 and higher Paraffin wax,
asphalt, and tar

Ch. 4 - 11
2. Shapes of Alkanes

 All carbon atoms in alkanes and

cycloalkanes are sp3 hybridized, and
they all have a tetrahedral geometry

 Even “straight-chain” alkanes are not

straight. They have a zigzag geometry

Ch. 4 - 12
 “Straight-chain” (unbranched) alkanes

Butane Pentane
CH3CH2CH2CH3 CH3CH2CH2CH2CH3

Ch. 4 - 13
 Branched-chain alkanes
Isobutane Neopentane
CH3
CH3 CH CH3 CH3 C CH3
CH3 CH3

Ch. 4 - 14
 Butane and isobutane have the same
molecular formula (C4H10) but different
bond connectivities. Such compounds
are called constitutional isomers

Butane Isobutane

Ch. 4 - 15
 C4 and higher alkanes exist as
constitutional isomers. The number of
constitutional isomers increases rapidly
with the carbon number
Molecular # of Possible Molecular # of Possible
Formula Const. Isomers Formula Const. Isomers
C4H10 2 C9H20 35

C5H12 3 C10H22 75

C6H14 5 C20H42 366,319

C7H16 9 C40H82 62,481,801,147,341

C8H18 18
Ch. 4 - 16
 Constitutional isomers usually have
different physical properties
Hexane Isomers (C6H14)
Formula M.P. B.P. Density Refractive
(oC) (oC) (g/mL) Index
-95 68.7 0.6594 1.3748

-153.7 60.3 0.6532 1.3714

-118 63.3 0.6643 1.3765

-128.8 58 0.6616 1.3750

-98 49.7 0.6492 1.3688

Ch. 4 - 17
3. IUPAC Nomenclature of Alkanes,
Alkyl Halides, & Alcohols
 One of the most commonly used
nomenclature systems that we use
today is based on the system and rules
developed by the International Union
of Pure and Applied Chemistry (IUPAC)

 Fundamental Principle: Each different

compound shall have a unique name

Ch. 4 - 18
 Although the IUPAC naming system is
now widely accepted among chemists,
common names (trivial names) of
some compounds are still widely used
by chemists and in commerce. Thus,
learning some of the common names
of frequently used chemicals and
compounds is still important

Ch. 4 - 19
 The ending for all the names of
alkanes is –ane

 The names of most alkanes stem from

Greek and Latin

one two three four five

meth- eth- prop- but- pent-

Ch. 4 - 20
 Unbranched alkanes

Name Structure Name Structure

Methane CH4 Hexane CH3(CH2)4CH3
Ethane CH3CH3 Heptane CH3(CH2)5CH3
Propane CH3CH2CH3 Octane CH3(CH2)6CH3
Butane CH3CH2CH2CH3 Nonane CH3(CH2)7CH3
Pentane CH3(CH2)3CH3 Decane CH3(CH2)8CH3

Ch. 4 - 21
3A. Nomenclature of Unbranched
Alkyl Groups

 Alkyl group
● Removal of one hydrogen atom
from an alkane

Ch. 4 - 22
 Alkyl group (Cont’d)
● For an unbranched alkane, the
hydrogen atom that is removed is a
terminal hydrogen atom
CH3 H CH3CH2 H CH3CH2CH2 H
Methane Ethane Propane

CH3 CH3CH2 CH3CH2CH2

Methyl Ethyl Propyl
(Me) (Et) (Pr)
Ch. 4 - 23
3B. Nomenclature of Branched-Chain
Alkanes
 Rule
1. Use the longest continuous carbon
chain as parent name
7 6 5 4 3 6 5 4 3 2 1
CH3CH2CH2CH2CHCH3 CH3CH2CH2CH2CHCH3
2CH2 CH2
NOT
1 CH3 CH3
(3-Methylheptane) (2-Ethylhexane)

Ch. 4 - 24
 Rule (Cont’d)
2. Use the lowest number of the
substituent
3. Use the number obtained by
Rule 2 to designate the location of
the substituent
7 6 5 4 3 1 2 3 4 5
CH3CH2CH2CH2CHCH3 CH3CH2CH2CH2CHCH3
2CH2 6 CH2
NOT
1 CH3 7 CH3
(3-Methylheptane) (5-Methylheptane)
Ch. 4 - 25
 Rule (Cont’d)
4. For two or more substituents, use
the lowest possible individual
numbers of the parent chain
The substitutents should be listed
alphabetically. In deciding
alphabetical order, disregard
multiplying prefix, such as “di”,
“tri” etc.

Ch. 4 - 26
 Rule (Cont’d)

2 4 6 8
1 3 5 7
(6-Ethyl-2-methyloctane)

NOT NOT

7 5 3 1 2 4 6 8
8 6 4 2 1 3 5 7
(3-Ethyl-7-methyloctane) (2-Methyl-6-ethyloctane)
Ch. 4 - 27
 Rule (Cont’d)
5. When two substituents are present
on the same carbon, use that
number twice

2 4 6 8
1 3 5 7
(4-Ethyl-4-methyloctane)

Ch. 4 - 28
 Rule (Cont’d)
6. For identical substituents, use
prefixes di-, tri-, tetra- and so on
5 3 1
6 4 2 7 5 3 1
6 4 2

(2,4-Dimethylhexane) (2,4,5-Trimethylheptane)

NOT NOT
2 4 6
1 3 5 1 3 5 7
2 4 6

(3,5-Dimethylhexane) (3,4,6-Trimethylheptane)
Ch. 4 - 29
 Rule (Cont’d)
7. When two chains of equal length
compete for selection as parent
chain, choose the chain with the
greater number of substituents
7 1 1
6 4 2 4 2
5 3 3

5
NOT 6
7
(2,3,5-Trimethyl- (only three substituents)
4-propylheptane)
Ch. 4 - 30
 Rule (Cont’d)
8. When branching first occurs at an
equal distance from either end of
the longest chain, choose the
name that gives the lower number
at the first point of difference

6 1
NOT
5 3 1 2 4 6
4 2 3 5

(2,3,5-Trimethylhexane) (2,4,5-Trimethylhexane)

Ch. 4 - 31
 Example 1

● Find the longest chain as parent

4 2 4 6
3 1 5 7
or
5 7 3 1
6 2

Ch. 4 - 32
 Example 1 (Cont’d)
● Use the lowest numbering for
substituents
4 6 4 2
5 7 3 1
instead of
3 1 5 7
2 6

● Substituents: two methyl groups

 dimethyl 4 6
5 7

3 1
2
Ch. 4 - 33
 Example 1 (Cont’d)
● Complete name
4 6
5 7

3 1
2

(3,4-Dimethylheptane)

Ch. 4 - 34
 Example 2

Ch. 4 - 35
 Example 2 (Cont’d)
● Find the longest chain as parent

6-carbon chain 8-carbon chain 8-carbon chain

Ch. 4 - 36
 Example 2 (Cont’d)
● Find the longest chain as parent

9-carbon chain
(correct!)

⇒ Nonane as parent
Ch. 4 - 37
 Example 2 (Cont’d)
● Use the lowest numbering for
substituents
8 2
7 3
9 1
6 4
5 instead of 5
2 8
3 7 6
4
1 9

(3,4,7) (3,6,7)

Ch. 4 - 38
 Example 2 (Cont’d)
● Substituents
 3,7-dimethyl
 4-ethyl
8
7
9
6
5
2
3
4
1

Ch. 4 - 39
 Example 2 (Cont’d)
● Substituents in alphabetical order
 Ethyl before dimethyl
(recall Rule 4 – disregard “di”)
● Complete name
8
7
9
6
5
2
3
4
1

(4-Ethyl-3,7-dimethylnonane)
Ch. 4 - 40
3C. Nomenclature of Branched Alkyl
Groups
 For alkanes with more than two carbon
atoms, more than one derived alkyl
group is possible
 Three-carbon groups

Propyl Isopropyl
(or 1-methylethyl)
Ch. 4 - 41
 Four-carbon groups

Butyl Isobutyl

sec-butyl tert-butyl
(1-methylpropyl) (or 1,1-dimethylethyl)
Ch. 4 - 42
 A neopentyl group

neopentyl
(2,2,-dimethylpropyl)

Ch. 4 - 43
 Example 1

Ch. 4 - 44
 Example 1 (Cont’d)
● Find the longest chain as parent
(a) (b)

6-carbon 7-carbon
chain chain

(c) (d)

8-carbon 9-carbon
chain chain
Ch. 4 - 45
 Example 1 (Cont’d)
● Find the longest chain as parent
(d)

⇒ Nonane as parent

1 3 4 5 6 7 8 9 9 7 6 5 4 3 2 1
2 or 8

Ch. 4 - 46
 Example 1 (Cont’d)
● Use the lowest numbering for
substituents

1 3 4 5 6 7 8 9 9 7 6 5 4 3 2 1
2 or 8

5,6 4,5
(lower numbering)

⇒ Use 4,5
Ch. 4 - 47
 Example 1 (Cont’d)
● Substituents
 Isopropyl
 tert-butyl

9 8 7 6 5 4 3 2 1

⇒ 4-isopropyl and 5-tert-butyl

Ch. 4 - 48
 Example 1 (Cont’d)
● Alphabetical order of substituents
 tert-butyl before isopropyl

● Complete name

9 8 7 6 5 4 3 2 1

5-tert-Butyl-4-isopropylnonane
Ch. 4 - 49
 Example 2

Ch. 4 - 50
 Example 2 (Cont’d)
● Find the longest chain as parent
(a) (b)

8-carbon 9-carbon
chain chain

(c)
⇒ Octane as parent

10-carbon
chain
Ch. 4 - 51
 Example 2 (Cont’d)

1 2 3 4 5 6 7 8 9 10

or

10 9 8 7 6 5 4 3 2
1

Ch. 4 - 52
 Example 2 (Cont’d)
● Use the lowest numbering for
substituents
5,6
1 2 3 4 5 6 7 8 9 10

or 5,6
10 9 8 7 6 5 4 3 2
1
⇒ Determined using
the next Rules
Ch. 4 - 53
 Example 2 (Cont’d)
● Substituents
 sec-butyl
 Neopentyl

But is it
● 5-sec-butyl and 6-neopentyl or
● 5-neopentyl and 6-sec-butyl ?
Ch. 4 - 54
 Example 2 (Cont’d)
● Since sec-butyl takes precedence
over neopentyl
 5-sec-butyl and 6-neopentyl

● Complete name

10 9 8 7 6 5 4 3 2
1

5-sec-Butyl-6-neopentyldecane Ch. 4 - 55
3D. Classification of Hydrogen Atoms

1o hydrogen atoms

CH3
CH3 CH CH2 CH3

3o hydrogen atoms 2o hydrogen atoms

Ch. 4 - 56
3E. Nomenclature of Alkyl Halides
 Rules
● Halogens are treated as
substituents (as prefix)
F: fluoro Br: bromo
Cl: chloro I: iodo

● Similar rules as alkyl substituents

Ch. 4 - 57
 Examples
3 1
4 2
Cl
Br
2-Bromo-1-chlorobutane

Cl
2 6
Cl 1 3 4 5

CH3
1,4-Dichloro-3-methylhexane

Ch. 4 - 58
3F. Nomenclature of Alcohols
 IUPAC substitutive nomenclature:
a name may have as many as four
features
● Locants, prefixes, parent compound,
and suffixes

6 5 4 3 2 1 OH
4-Methyl-1-hexanol

Ch. 4 - 59
 Rules
● Select the longest continuous carbon
chain to which the hydroxyl is directly
attached. Change the name of the
alkane corresponding to this chain by
dropping the final –e and adding the
suffix –ol
● Number the longest continuous carbon
chain so as to give the carbon atom
bearing the hydroxyl group the lower
number. Indicate the position of the
hydroxyl group by using this number as
a locant Ch. 4 - 60
 Examples
OH
OH
2 1
3 1 4 3 2 OH
2-Propanol OH
(isopropyl alcohol) 1,2,3-Butanetriol
5 1
4 3 2
OH

4-Methyl-1-pentanol
(or 4-Methylpentan-1-ol)
(NOT 2-Methyl-5-pentanol)
Ch. 4 - 61
 Example 4

OH

Ch. 4 - 62
 Example 4 (Cont’d)
● Find the longest chain as parent
8
7
6
3 1 or 1 5 7
4 2 2 4 6
5 3

OH OH
Longest chain but 7-carbon chain
does not contain containing the
the OH group OH group

⇒ Heptane as parent
Ch. 4 - 63
 Example 4 (Cont’d)
● Use the lowest numbering for the
carbon bearing the OH group

1 5 7 7 3 1
2
3
4 6 or 6
5
4 2

OH 2,3 OH 5,6
(lower numbering)

⇒ Use 2,3
Ch. 4 - 64
 Example 4 (Cont’d)
● Parent and suffix
 2-Heptanol
1 5 7
2 4 6
3
● Substituents
OH
 Propyl

● Complete name
 3-Propyl-2-heptanol

Ch. 4 - 65
4. How to Name Cycloalkanes

4A. Monocyclic Compounds

 Cycloalkanes with only one ring
● Attach the prefix cyclo-

H2C CH2 = H2C CH2 =

C H2C CH2
H2 C
Cyclopropane H2
Cyclopentane
Ch. 4 - 66
 Substituted cycloalkanes

Isopropylcyclopropane Methylcyclopropane

tert-Butylcyclopentane
Ch. 4 - 67
 Example 1

4 3 2
1-Ethyl-3-methyl-
1
cyclopentane
5

NOT NOT
3 4 5 5 1 2
2 1 4 3

1-Ethyl-4-methyl- 3-Ethyl-1-methyl-
cyclopentane cyclopentane
Ch. 4 - 68
 Example 2
Br
5 4 3 4-Bromo-2-ethyl-1-methyl
6 1
2 cyclohexane

NOT Br
6 1 2 1-Bromo-3-ethyl-4-methyl
5 4
3 cyclohexane
(lowest numbers of substituents
are 1,2,4 not 1,3,4)
Ch. 4 - 69
 Example 3

4
3 2 4-Ethyl-3-methyl
5 6
1 cyclohexanol
OH

NOT

1
2 3 1-Ethyl-2-methyl
6 5
4 cyclohexan-4-ol
OH

(the carbon bearing the OH should have the lowest

numbering, even though 1,2,4 is lower than 1,3,4)
Ch. 4 - 70
 Cycloalkylalkanes
● When a single ring system is
attached to a single chain with a
greater number of carbon atoms

1-Cyclobutylpentane

● When more than one ring system

is attached to a single chain

1,3-Dicyclohexylpropane
Ch. 4 - 71
5. Nomenclature of Alkenes &
Cycloalkenes
 Rule
1. Select the longest chain that
contains C=C as the parent name
and change the name ending of
the alkane of identical length from
–ane to
–ene

Ch. 4 - 72
 Rule
2. Number the chain so as to include
both carbon atoms of C=C, and
begin numbering at the end of the
chain nearer C=C. Assign the
location of C=C by using the
number of the first atom of C=C
as the prefix. The locant for the
alkene suffix may precede the
parent name or be placed
immediately before the suffix
Ch. 4 - 73
● Examples
1 2 3 4
CH2 CHCH2CH3
1-Butene
(not 3-Butene)

1 2 3 4 5 6
CH3CH CHCH2CH2CH3
2-Hexene
(not 4-Hexene)

Ch. 4 - 74
 Rule
3. Indicate the locations of the
substituent groups by the numbers
of the carbon atoms to which they
are attached
● Examples
4
3
2
1
2-Methyl-2-butene
(not 3-Methyl-2-butene)
Ch. 4 - 75
● Examples (Cont’d)
4 6
3 5
2
1
2,5-Dimethyl-2-hexene

3 1
NOT 4 2
5
6
2,5-Dimethyl-4-hexene

Ch. 4 - 76
 Rule
4. Number substituted cycloalkenes
in the way that gives the carbon
atoms of C=C the 1 and 2
positions and that also gives the
substituent groups the lower
numbers at the first point of
difference

Ch. 4 - 77
● Example
1
6 2

5 3
4
3,5-Dimethylcyclohexene

2
NOT 3 1

4 6
5
4,6-Dimethylcyclohexene
Ch. 4 - 78
 Rule
5. Name compounds containing a
C=C and an alcohol group as
alkenols (or cycloalkenols) and
give the alcohol carbon the lower
number
● Examples OH
6 1
2
5
3
4
2-Methyl-2-cyclohexen-1-ol
(or 2-Methylcyclohex-2-en-1-ol)
Ch. 4 - 79
● Examples (Cont’d)

OH
4 2
5 3 1
4-Methyl-3-penten-2-ol
(or 4-Methylpent-3-en-2-ol)

Ch. 4 - 80
 Rule
6. Vinyl group & allyl group
Vinyl group Allyl group

ethenyl prop-2-en-1-yl
OH
6 1 2

5
Ethenylcyclopropane 3
4
(or Vinylcyclopropane) 3-(Prop-2-en-1-yl)
cyclohexan-1-ol
(or 3-Allylcyclohexanol)
Ch. 4 - 81
 Rule
7. Cis vs. Trans
● Cis: two identical or substantial
groups on the same side of C=C
● Trans: two identical or
substantial groups on the
opposite side of C=C
Cl

Cl Cl Cl
cis-1,2-Dichloroethene trans-1,2-Dichloroethene
Ch. 4 - 82
 Example

Ch. 4 - 83
 Example (Cont’d)

6 (a) (b)
5 7
6
4 2 4 2
3 1 5 3 1

(c) (d)

6 2
4 2 4 6
7 5 3 1 1 3 5 7

Ch. 4 - 84
 Example (Cont’d)
● Complete name

2
4 6
1 3 5 7

4-tert-Butyl-2-methyl-1-heptene

Ch. 4 - 85
6. Nomenclature of Alkynes

 Alkynes are named in much the same

way as alkenes, but ending name with
–yne instead of –ene

 Examples
6 4 3 2 1 2 3
Br
1
7 5 4

2-Heptyne 4-Bromo-1-butyne
Ch. 4 - 86
 Examples (Cont’d)

3 4
I Br
2
5 6 7 8 9
1 10

9-Bromo-7-iodo-6-isopropyl-8-methyl-3-decyne

Ch. 4 - 87
 OH group has priority over C≡C
4 3 1 2
2 3
OH NOT OH
1 4
3-Butyn-1-ol

OH 5 6 7 OH 4 3 2
2 4 7 5
1 3 8 8 6 1
2-Methyl-5-octyn-2-ol NOT

Ch. 4 - 88
7. Physical Properties of
Alkanes & Cycloalkanes
 Boiling points & melting points

Ch. 4 - 89
C6H14 Isomer Boiling Point (oC)

68.7

63.3

60.3

58

49.7
Ch. 4 - 90
1. The Discovery of Benzene

 Benzene: or

 In 1825, Faraday isolated benzene

from a compressed illuminating gas
that had been made by pyrolyzing
whale oil

Ch. 14 - 91
 In 1834, a German chemist, Eilhardt
Mitscherlich, synthesized benzene by
heating benzoic acid with calcium oxide

COOH

heat
+ CaO + CaCO3

Ch. 14 - 92
 In 19th century, organic compounds
were classified as being either
aliphatic or aromatic
 Aliphatic
● The chemical behavior of a
compound was “fatlike”
 Aromatic
● The compound had a low
hydrogen-to-carbon ratio and it was
“fragrant”

Ch. 14 - 93
2. Nomenclature of Benzene
Derivatives
 Naming monosubstituted benzenes
● In many simple compounds, benzene is
the parent name and the substituent is
simply indicated by a prefix
F Cl Br NO2

Fluorobenzene Chlorobenzene Bromobenzene Nitrobenzene

Ch. 14 - 94
 ● For other simple and common
compounds, the substituent and the
benzene ring taken together may form a
commonly accepted parent name
H H H CH3
CH3 O N SO3H O

Toluene Phenol Aniline Benzene- Anisole

sulfonic acid
O O

OH
Benzoic acid Acetophenone
Ch. 14 - 95
 Naming disubstituted benzenes
● When two substituents are present,
their relative positions are indicated by
the prefixes ortho-, meta-, and para-
(abbreviated o-, m-, and p-) or by the
use of numbers
Br
Br Br

Br Br Br

1,2-Dibromobenzene 1,3-Dibromobenzene 1,4-Dibromobenzene

(o-dibromobenzene) (m-dibromobenzene) (p-dibromobenzene)
ortho meta para
Ch. 14 - 96
 ● Other examples
CH3
NO2 Cl

COOH OH CH3

2-Nitrobenzoic acid 3-Methylphenol 4-Chlorotoluene

(o-Nitrobenzoic acid) (m-Methylphenol) (p-Chlorotoluene)
(1-Chloro-4-methyl-
benzene)

Ch. 14 - 97
 ● The dimethylbenzenes are often
called xylenes

CH3
CH3 H3C

CH3 CH3 CH3

1,2-Dimethylbenzene 1,3-Dimethylbenzene 1,4-Dimethylbenzene

(o-xylene) (m-xylene) (p-xylene)

Ch. 14 - 98
  Naming benzene rings with more than
two groups
● If more than two groups are present on
the benzene ring, their positions must
be indicated by the use of numbers
● The benzene ring is numbered so as to
give the lowest possible numbers to
the substituents
Cl Br
1 1
2 Cl 2 Br
6 6

5
3
5
3 1,2,4-Tribromobenzene
4 Cl 4 (not 1,3,4-Tribromobenzene)
1,2,3-Trichlorobenzene Br Ch. 14 - 99
● When more than two substituents
are present and the substituents
are different, they are listed in
alphabetical order
Cl
1
2 F
6

3
5
4

Br
4-Bromo-1-chloro-2-fluorobenzene
Ch. 14 - 100
 ● When a substituent is one that,
together with the benzene ring
gives a new base name, that
substituent is assumed to be in
position 1 and the new parent
name is used
Cl COOH
3 1
H3C 2
4 2 6

5 1
3
5
Cl 6 OH 4 Br
3,5-Dichlorophenol 5-Bromo-2-methylbenzoic acid
Ch. 14 - 101
● When the C6H5 group is named as a
substituent, it is called a phenyl
group
● A hydrocarbon composed of one
saturated chain and one benzene
ring is usually named as a
derivative of the larger structural
unit. However, if the chain is
unsaturated, the compound may be
named as a derivative of that chain,
regardless of ring size
Ch. 14 - 102
 ● Examples

Butylbenzene Isopropylbenzene

2 4
1 3 5 7
1 3 2 4 6 8
trans-1-Phenyl-1-butene (R)-3-Phenyloctane
Ch. 14 - 103
 ● Benzyl is an alternative name for
the phenylmethyl group. It is
sometimes abbreviated Bn

Cl

The benzyl group Benzyl chloride

(the phenylmethyl group) (phenylmethyl chloride
or BnCl)

Ch. 14 - 104
8. Other Aromatic Compounds
8A. Benzenoid Aromatic Compounds
 Benzenoid polycyclic aromatic hydrocarbons
consist of molecules having two or more
benzene rings fused together
8 1 8 9 1
2 2
Naphthalene 7 7 Anthracene
C10H8 3 3
C14H10
6 6
5 4 5 10 4

6 9 8
5 7 10 7

4
8 6
3
Phenanthrene 1 Pyrene
C14H10 C16H10
2 9 2 5
1 10 3 4 Ch. 14 - 105
9. Heterocyclic Aromatic Compounds

 Cyclic compounds that include an

element other than carbon are called
heterocyclic compounds
4 4 3 4 3 4 3
5 3
5 2 5 2 5 2

6 2 N1 O1 S1
N
1 H
Pyridine Pyrrole Furan Thiophene
(electronically
related to
benzene) (electronically related to
cyclopentadienyl anion)
Ch. 14 - 106
 NH2
 Examples of useful heterocyclic
aromatic compounds HO
HOOC H
N N
S
Serotonin H
O N (neurotransmitter)
S O O
Penicillin COOH H
(antibiotic) N
O N
N
O
N
N H
N N
O2N
O
Nitrofurantoin O O S N N
(urinary antibacterial) "Viagra"
O Ch. 14 - 107