Chapter 11
Haloalkanes, Alkenes, and Alkynes
Functional Groups
Haloalkanes
Timberlake LecturePLUS 1999
1
Functional Groups
 Part of an organic molecule where



chemical reactions take place
Composed of an atom or group of atoms
Replace a H in the corresponding alkane
Provide a way to classify organic
compounds
Timberlake LecturePLUS 1999
2
Some Types of Functional Groups
Haloalkane
Alcohol
-F, -Cl, -Br CH3Cl
-OH
CH3OH
Ether
-O-
CH3-O-CH3
O
O
Aldehyde
Ketone
C H
O
CH3CH
C
CH3CCH3
O
Timberlake LecturePLUS 1999
3
More Functional Groups
Carboxylic acid -COOH
CH3COOH
Ester
-COO-
CH3COOCH3
Amine
-NH2
CH3NH2
Amide
-CONH2
CH3CONH2
Timberlake LecturePLUS 1999
4
Haloalkanes
An alkane in which one or more H atoms is
replaced with a halogen (F, Cl, Br, or I)
CH3Br
1-bromomethane
(methyl bromide)
Br
CH3CH2CHCH3
2-bromobutane
Cl
chlorocyclobutane
Timberlake LecturePLUS 1999
5
Learning Check HA1
Name the following:
Br
Cl
Cl
Timberlake LecturePLUS 1999
6
Solution HA1
Name the following:
Br
bromocyclopentane
Cl
1,3-dichlorocyclohexane
Cl
Timberlake LecturePLUS 1999
7
Substituents
List other attached atoms or group in
alphabetical order
Br = bromo, Cl = chloro
Cl
Br
CH3CHCH2CHCH2CH2CH3
4-bromo-2-chloroheptane
Timberlake LecturePLUS 1999
8
Learning Check HA2
The name of this compound is:
Cl
CH3
CH3CH2CHCH2CHCH3
1)
2,4-dimethylhexane
2)
3-chloro-5-methylhexane
3)
4-chloro-2-methylhexane
Timberlake LecturePLUS 1999
9
Solution HA2
The name of this compound is:
Cl
CH3
CH3CH2CHCH2CHCH3
3) 4-chloro-2-methylhexane
Timberlake LecturePLUS 1999
10
Haloalkanes as Anesthetics
Halothane (Fluothane)
F Cl
F
C
C
Br
F
H
Fluothane is a haloalkane that is widely used
as an anesthetic, which is a compound that
decreases the ability of the nerve cells to
conduct pain.
Timberlake LecturePLUS 1999
11
Ozone Layer
Ozone layer
Stratosphere
(10-30 miles
Above Earth)
Timberlake LecturePLUS 1999
12
Chlorofuorocarbons (CFCs and
the Ozone Layer
ozone O3 layer absorbs most of the
sun’s harmful radiation.
CFCs - chlorofluorocarbons - are
depleting that ozone layer.
CFCs are used as Freons in
refrigeration,
air conditioning, and foam insulation.
Their use in spray cans is no longer
allowed.
Timberlake LecturePLUS 1999
13
Chlorofuorocarbons and the
Ozone Layer
In the stratosphere, the CFCs react with
the high-energy UV radiation from the sun
CF2Cl2
Freon-12
UV light
CF2Cl + Cl
free radical
Timberlake LecturePLUS 1999
14
Chlorofuorocarbons and the
Ozone Layer
To become stable, the Cl acquires an electron
from ozone O3 and produces ClO.
Cl
+
O3
ClO + O2
The presence of ClO in the atomosphere is an
indicator of the disappearance of ozone.
Timberlake LecturePLUS 1999
15
Impact of Loss of Ozone Layer
According to the National Academy of
Sciences, each 1% loss of ozone increases
by 2% the amount of UV radiation reaching
the earth. More UV radiation means more
skin cancer and cataracts in humans, more
intense photochemical smog, and lower crop
yields.
Timberlake LecturePLUS 1999
16