Chapter 10

Alkanes and Aromatic

Hydrocarbons

Cycloalkanes
Aromatic Hydrocarbons

  Timberlake LecturePLUS 1999 1
 Cycloalkanes
Cyclopropane CH2

CH2 CH2

Cyclobutane
CH2 CH2

CH2 CH2

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 More Cycloalkanes

Cyclopentane CH2

CH2 CH2
CH2 CH2
Cyclohexane
CH2
CH2 CH2

  Timberlake LecturePLUS 1999
CH2 CH2 3
 Naming Cycloalkanes with
Side Groups
Number of Naming
side groups
One Side group name goes in front
of the cycloalkane name.
Two Number the ring in the direction
that gives the lowest numbers
to the side groups.

  Timberlake LecturePLUS 1999 4
Cycloalkanes with Side Groups
CH3

methylcyclopentane

CH3
CH3
1,2-dimethylcyclopentane

CH3
CH3

1,2,4-trimethylcyclohexane

CH3
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 Learning Check Alk8
CH3

CH3
CH3

CH3

CH3
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 Solution Alk8

CH3

1,2-dimethylcyclobutane
CH3
CH3

methylcyclopentane

CH3

1,3-dimethylcyclohexane

CH3

  Timberlake LecturePLUS 1999 7
 Aromatic Compounds and
Benzene
Aromatic compounds contain benzene.
Benzene, C6H6 , is represented as a six
carbon ring with 3 double bonds.
Two possible can be drawn to show benzene
in this form. H H
H H H H

H H H H

H H
  Timberlake LecturePLUS 1999 8
 Benzene Structure
The structures for benzene can also be
written as a single structure where the
alternating double bonds are written as a
circle within the ring.

Benzene
structure

  Timberlake LecturePLUS 1999 9
 Aromatic Compounds in Nature
and Health
Many aromatic compounds are common in nature
and in medicine.
CHO
COOH
COOCH3 CH3 CH3
CH3CHCH2 CHCOOH
OCH3
OH

Aspirin Vanillin Ibuprofen

  Timberlake LecturePLUS 1999 10
 Naming Aromatic Compounds
Aromatic compounds are named with
benzene as the parent chain. One side group
is named in front of the name benzene.

CH3 Cl

methylbenzene chlorobenzene
(toluene)
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 Naming Aromatic Compounds

When two groups are attached to benzene, the

ring is numbered to give the lower numbers to the
side groups. The prefixes ortho (1,2), meta (1,3-)
and para (1,4-) are also used.
Cl
CH 3 Cl
CH 3

Cl CH 3

1,2-dimethylbenzene 1,3-dichlorobenzene 1-chloro-4-methylbenzene

(ortho-dimethylbenzene) (meta-dichlorobenzene) (para-chloromethylbenzene)

  Timberlake LecturePLUS 1999 12
 Some Common Names

Some substituted benzene rings also use a

common name. Then naming with additional more
side groups uses the ortho-, meta-, para- system.
CH3 CH3 OH

Cl
Toluene meta-chlorotoluene phenol
(Methylbenzene) (meta-chloromethylbenzene) (hydroxybenzene)

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 Learning Check Alk9
Select the names for each structure:
Cl
1. Chlorocyclohexane
2. Chlorobenzene
3. 1-chlorobenzene
CH3
1. Meta-methyltoluene
2. Meta-dimethylbenzene
3. 1,3-dimethylbenzene
CH3
  Timberlake LecturePLUS 1999 14
 Solution Alk9
Select the names for each structure:
Cl
2. Chlorobenzene

CH3 1. Meta-methyltoluene
2. Meta-dimethylbenzene
3. 1,3-dimethylbenzene
CH3
  Timberlake LecturePLUS 1999 15
 Learning Check Alk10

Write the structural formulas for each of the

following:
A. 1,3-dichlorobenzene

B. Ortho-chlorotoluene

  Timberlake LecturePLUS 1999 16
 Solution Alk10

Write the structural formulas for each of the

following: Cl

A. 1,3-dichlorobenzene

Cl
CH 3
B. Ortho-chlorotoluene Cl

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