340 Chapter 11 Unsaturated Hydrocarbons

Recycled HDPE is converted to Tyvek, an insulating wrap used in new housing construction, and
recycled PET is used to make fibers for fleece clothing and carpeting. Currently about 23% of all
plastics are recycled in the United States.

11.8 Aromatic Compounds

Aromatic compounds represent another example of unsaturated hydrocarbons. Aromatic com-
pounds were originally named because many simple compounds in this family have characteris-
tic odors. Today, the word aromatic refers to compounds that contain a benzene ring, or rings
that react in a similar fashion to benzene.

HEALTH NOTE Benzene, the simplest and most widely known aromatic compound, contains a six-membered
ring and three double bonds. Since each carbon of the ring is also bonded to a hydrogen atom,
the molecular formula for benzene is C6H6. Each carbon is surrounded by three groups, making
it trigonal planar. Thus, benzene is a planar molecule, and all bond angles are 120°.

H
H C H
C C
= = 120°
C C
H C H

Tamoxifen, a potent anticancer drug H

sold under the trade name of Novaldex, benzene planar molecule
contains three benzene rings. C6H6

OCH2CH2N(CH3)2
Although benzene is drawn with a six-membered ring and three double bonds, there are two dif-
ferent ways to arrange the double bonds so that they alternate with single bonds around the ring.
Each of these representations is equivalent.

C C tamoxifen
CH3CH2 or

This bond is a single bond in one structure

and a double bond in the second structure.

The physical properties of aromatic hydrocarbons are similar to other hydrocarbons—they have
low melting points and boiling points and are water insoluble.

11.9 Nomenclature of Benzene Derivatives

Many organic molecules contain a benzene ring with one or more substituents, so we must learn
how to name them.

11.9A Monosubstituted Benzenes

To name a benzene ring with one substituent, name the substituent and add the word benzene.
Carbon substituents are named as alkyl groups. When a halogen is a substituent, name the
halogen by changing the -ine ending of the name of the halogen to the suffix -o; for example,
chlorine → chloro.

CH2CH3 CH2CH2CH2CH3 Cl

ethyl group butyl group chloro group

ethylbenzene butylbenzene chlorobenzene

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 11.9 Nomenclature of Benzene Derivatives 341

Many monosubstituted benzenes, such as those with methyl (CH3–), hydroxyl (–OH), and amino
(–NH2) groups, have common names that you must learn, too.

CH3 OH NH2

toluene phenol aniline

(methylbenzene) (hydroxybenzene) (aminobenzene)

11.9B Disubstituted Benzenes

There are three different ways that two groups can be attached to a benzene ring, so a prefix—
ortho, meta, or para—is used to designate the relative position of the two substituents. Ortho,
meta, and para are generally abbreviated as o, m, and p, respectively.

1,2-Disubstituted benzene 1,3-Disubstituted benzene 1,4-Disubstituted benzene

ortho isomer meta isomer para isomer

CH2CH3 CH2CH3 CH2CH3

CH2CH3

CH2CH3
CH2CH3
o-diethylbenzene m-diethylbenzene p-diethylbenzene
or or or
1,2-diethylbenzene 1,3-diethylbenzene 1,4-diethylbenzene

If the two groups on the benzene ring are different, alphabetize the name of the substituents
The pain reliever acetaminophen preceding the word benzene. If one of the substituents is part of a common root, name the mol-
(trade name Tylenol) contains a para- ecule as a derivative of that monosubstituted benzene.
disubstituted benzene ring.
H Alphabetize two different substituent names: Use a common root name:
N CH3 Br CH2CH3 toluene phenol
C Cl
Cl
O
HO
Br CH3 OH
acetaminophen
F
(Trade name: Tylenol)
o-bromochloro- m-ethylfluoro-
benzene benzene p-bromotoluene o-chlorophenol

11.9C Polysubstituted Benzenes

For three or more substituents on a benzene ring:

1. Number to give the lowest possible numbers around the ring.

2. Alphabetize the substituent names.
3. When substituents are part of common roots, name the molecule as a derivative of that
monosubstituted benzene. The substituent that comprises the common root is located at C1,
but the “1” is omitted from the name.

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 342 Chapter 11 Unsaturated Hydrocarbons

Examples of naming polysubstituted benzenes

1
NH2
CH2CH3 Cl 1
2

Cl CH2CH2CH3 Cl

4 2
• Assign the lowest set of numbers.
• Alphabetize the names of all the
substituents.
4-chloro-1-ethyl-2-propylbenzene
5
• Name the molecule as a derivative of the
common root aniline.
• Designate the position of the NH2 group as “1,”
and then assign the lowest possible set of
numbers to the other substituents.
2,5-dichloroaniline

SAMPLE PROBLEM 11.7

Name each of the following aromatic compounds.
CH3CH2 CH2CH2CH3 CH3 Cl
a. b.
Br
Analysis
Name the substituents on the benzene ring. With two groups, alphabetize the substituent names and
use the prefix ortho, meta, or para to indicate their location. With three substituents, alphabetize the
substituent names, and number to give the lowest set of numbers.

Solution
a. CH3CH2 CH2CH2CH3 • The two substituents are located 1,3- or meta to
each other.
ethyl propyl
group group • Alphabetize the e of ethyl before the p of propyl.
Answer: m-ethylpropylbenzene
1
b. CH3 Cl • Since a CH3– group is bonded to the ring, name the
3
molecule as a derivative of toluene.
4
Br • Place the CH3 group at the “1” position, and
number to give the lowest set of numbers.
toluene
Answer: 4-bromo-3-chlorotoluene

PROBLEM 11.18
Give the IUPAC name of each compound.
OH
CH2CH2CH3
a. c.
CH2CH2CH2CH3

CH3
CH2CH3 Br
b. d.
I Cl

PROBLEM 11.19
Draw the structure corresponding to each name.
a. pentylbenzene c. m-bromoaniline
b. o-dichlorobenzene d. 4-chloro-1,2-diethylbenzene

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 11.10 FOCUS ON HEALTH & MEDICINE: Sunscreens and Antioxidants 343

11.10 FOCUS ON HEALTH & MEDICINE

Sunscreens and Antioxidants
HEALTH NOTE 11.10A Sunscreens
All commercially available sunscreens contain a benzene ring. A sunscreen absorbs ultraviolet
radiation and thus shields the skin for a time from its harmful effects. Two sunscreens that have
been used for this purpose are p-aminobenzoic acid (PABA) and Padimate O.
O O
H2N C (CH3)2N C
OH OCH2CHCH2CH2CH2CH3

p-aminobenzoic acid Padimate O CH2CH3

(PABA)

PROBLEM 11.20
Identify the functional groups in each sunscreen: (a) PABA; (b) Padimate O.

PROBLEM 11.21
Which of the following compounds might be an ingredient in a commercial sunscreen? Explain why
or why not.
O O

a. b.

Commercial sunscreens are given an CH3O OH

SPF rating (sun protection factor),
according to the amount of sunscreen
present. The higher the number, the
greater the protection.
11.10B Phenols as Antioxidants
A wide variety of phenols, compounds that contain a hydroxyl group bonded to a benzene ring,
occur in nature. Vanillin from the vanilla bean is a phenol, as is curcumin, a yellow pigment
isolated from turmeric, a tropical perennial in the ginger family and a principal ingredient in
curry powder. Curcumin has long been used as an anti-inflammatory agent in traditional eastern
medicine. In some preliminary research carried out with mice, curcumin was shown to correct the
defect that causes cystic fibrosis, a fatal genetic disease that afflicts 30,000 children and young
adults in the United States.

vanilla bean turmeric

OH H
H O O H
OCH3
C C C C
C C C

H H H
HO OH
CHO
OCH3 OCH3
vanillin curcumin

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 344 Chapter 11 Unsaturated Hydrocarbons

HEALTH NOTE Many phenols are antioxidants, compounds that prevent unwanted oxidation reactions from
occurring. Two examples are naturally occurring vitamin E and synthetic BHT. The OH group
on the benzene ring is the key functional group that prevents oxidation reactions from
taking place.
CH3
OH
HO
(CH3)3C C(CH3)3

(CH2)3CH(CH2)3CH(CH2)3CH(CH3)2
CH3 O
CH3 CH3 CH3
CH3 CH3
BHT
vitamin E (butylated hydroxy toluene)
The purported health benefits of
antioxidants have made them a popular Vitamin E is a natural antioxidant found in fish oil, peanut oil, wheat germ, and leafy greens.
component in anti-aging formulations. Although the molecular details of its function remain obscure, it is thought that vitamin E pre-
vents the unwanted oxidation of unsaturated fatty acid residues in cell membranes. In this way,
vitamin E helps retard the aging process.
HEALTH NOTE
Synthetic antioxidants such as BHT—butylated hydroxy toluene—are added to packaged and
prepared foods to prevent oxidation and spoilage. BHT is a common additive in breakfast cereals.

PROBLEM 11.22
Which of the following compounds might be antioxidants?

a. CH3 CH(CH3)2 b. curcumin c. CH3 CH3

OH p-xylene
Nuts are an excellent source of vitamin
(gasoline additive)
E. menthol

KEY TERMS
Addition reaction (11.5) Fatty acid (11.3) Para isomer (11.9)
Alkene (11.1) Hydration (11.5) Partial hydrogenation (11.6)
Alkyne (11.1) Hydrogenation (11.5) Polymer (11.7)
Antioxidant (11.10) Meta isomer (11.9) Polymerization (11.7)
Aromatic compound (11.8) Monomer (11.7) Stereoisomer (11.3)
Cis isomer (11.3) Oil (11.3) Trans isomer (11.3)
Fat (11.3) Ortho isomer (11.9) Unsaturated hydrocarbon (11.1)

KEY CONCEPTS
❶ What are the characteristics of alkenes, alkynes, and
aromatic compounds?
• Alkenes are unsaturated hydrocarbons that contain a carbon–
carbon double bond and have molecular formula CnH2n. Each
carbon of the double bond is trigonal planar. (11.1)
• Alkynes are unsaturated hydrocarbons that contain a carbon–
carbon triple bond and have molecular formula CnH2n – 2. Each
carbon of the triple bond is linear. (11.1)
• Benzene, molecular formula C6H6, is the most common
aromatic hydrocarbon. Benzene contains a six-membered ring
with three double bonds, and each carbon is trigonal planar.
(11.8)
❷ How are alkenes, alkynes, and substituted benzenes named?
• An alkene is identified by the suffix -ene, and the carbon chain
is numbered to give the C C the lower number. (11.2)

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