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Timberlake LecturePLUS 19 99 1 Chapter 11 Haloalkanes, Alkenes, and Alkynes Functional Groups Haloalkanes

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Page 1: Timberlake LecturePLUS 19991 Chapter 11 Haloalkanes, Alkenes, and Alkynes Functional Groups Haloalkanes

Timberlake LecturePLUS 1999 1

Chapter 11Haloalkanes, Alkenes, and Alkynes

Functional Groups

Haloalkanes

Page 2: Timberlake LecturePLUS 19991 Chapter 11 Haloalkanes, Alkenes, and Alkynes Functional Groups Haloalkanes

Timberlake LecturePLUS 1999 2

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

Page 3: Timberlake LecturePLUS 19991 Chapter 11 Haloalkanes, Alkenes, and Alkynes Functional Groups Haloalkanes

Timberlake LecturePLUS 1999 3

Some Types of Functional Groups

Haloalkane -F, -Cl, -Br CH3Cl

Alcohol -OH CH3OH

Ether -O- CH3-O-CH3

Aldehyde

KetoneC

O

CH3CH

O

C H

O

CH3CCH3

O

Page 4: Timberlake LecturePLUS 19991 Chapter 11 Haloalkanes, Alkenes, and Alkynes Functional Groups Haloalkanes

Timberlake LecturePLUS 1999 4

More Functional Groups

Carboxylic acid -COOH CH3COOH

Ester -COO- CH3COOCH3

Amine -NH2 CH3NH2

Amide -CONH2 CH3CONH2

Page 5: Timberlake LecturePLUS 19991 Chapter 11 Haloalkanes, Alkenes, and Alkynes Functional Groups Haloalkanes

Timberlake LecturePLUS 1999 5

Haloalkanes

An alkane in which one or more H atoms is replaced with a halogen (F, Cl, Br, or I)

CH3Br 1-bromomethane

Br (methyl bromide)

CH3CH2CHCH3 2-bromobutane

Cl

chlorocyclobutane

Page 6: Timberlake LecturePLUS 19991 Chapter 11 Haloalkanes, Alkenes, and Alkynes Functional Groups Haloalkanes

Timberlake LecturePLUS 1999 6

Learning Check HA1

Name the following:

Br

Cl

Cl

Page 7: Timberlake LecturePLUS 19991 Chapter 11 Haloalkanes, Alkenes, and Alkynes Functional Groups Haloalkanes

Timberlake LecturePLUS 1999 7

Solution HA1

Name the following:

bromocyclopentane

1,3-dichlorocyclohexane

Br

Cl

Cl

Page 8: Timberlake LecturePLUS 19991 Chapter 11 Haloalkanes, Alkenes, and Alkynes Functional Groups Haloalkanes

Timberlake LecturePLUS 1999 8

Substituents

List other attached atoms or group in alphabetical order

Br = bromo, Cl = chloro

Cl Br

CH3CHCH2CHCH2CH2CH3

4-bromo-2-chloroheptane

Page 9: Timberlake LecturePLUS 19991 Chapter 11 Haloalkanes, Alkenes, and Alkynes Functional Groups Haloalkanes

Timberlake LecturePLUS 1999 9

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

Page 10: Timberlake LecturePLUS 19991 Chapter 11 Haloalkanes, Alkenes, and Alkynes Functional Groups Haloalkanes

Timberlake LecturePLUS 1999 10

Solution HA2

The name of this compound is:

Cl CH3

CH3CH2CHCH2CHCH3

3) 4-chloro-2-methylhexane

Page 11: Timberlake LecturePLUS 19991 Chapter 11 Haloalkanes, Alkenes, and Alkynes Functional Groups Haloalkanes

Timberlake LecturePLUS 1999 11

Haloalkanes as Anesthetics

Halothane (Fluothane) F Cl

F C C Br

F HFluothane 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.

Page 12: Timberlake LecturePLUS 19991 Chapter 11 Haloalkanes, Alkenes, and Alkynes Functional Groups Haloalkanes

Timberlake LecturePLUS 1999 12

Ozone Layer

Ozone layer

Stratosphere

(10-30 miles

Above Earth)

Page 13: Timberlake LecturePLUS 19991 Chapter 11 Haloalkanes, Alkenes, and Alkynes Functional Groups Haloalkanes

Timberlake LecturePLUS 1999 13

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.

Page 14: Timberlake LecturePLUS 19991 Chapter 11 Haloalkanes, Alkenes, and Alkynes Functional Groups Haloalkanes

Timberlake LecturePLUS 1999 14

Chlorofuorocarbons and the Ozone Layer

In the stratosphere, the CFCs react with

the high-energy UV radiation from the sun

UV light

CF2Cl2 CF2Cl + Cl

Freon-12 free radical

Page 15: Timberlake LecturePLUS 19991 Chapter 11 Haloalkanes, Alkenes, and Alkynes Functional Groups Haloalkanes

Timberlake LecturePLUS 1999 15

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 atmosphere is an indicator of the disappearance of ozone.

Page 16: Timberlake LecturePLUS 19991 Chapter 11 Haloalkanes, Alkenes, and Alkynes Functional Groups Haloalkanes

Timberlake LecturePLUS 1999 16

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.