4
organic halide a compound of carbon and hydrogen in which one or more hydrogen atoms have been replaced by halogen atoms
Organic Halides
Organic halides are a group of compounds that includes many common products such as Freons (chlorofluorocarbons, CFCs) used in refrigerators and air conditioners, and Teflon (polytetrafluoroethene), the nonstick coating used in cookware and labware. While we use some organic halides in our everyday lives, many others are toxic and some are also carcinogenic, so their benefits must be balanced against potential hazards. Two such compounds, the insecticide DDT (dichlorodiphenyltrichloroethane) and the PCBs (polychlorinated biphenyls) used in electrical transformers, have been banned because of public concern about toxicity. In Section 1.3 you learned that when H atoms in an alkane are replaced by halogen atoms, the resulting organic halide is more specifically referred to as an alkyl halide.
1,2-dichloroethane
SAMPLE problem
C
1
C
2
C
3
C
4
C
5
C
6
Next, add two Br atoms to carbon 2, one Br atom to carbon 5, and a methyl group to carbon 5.
Br C
1
Br C
3
C
2
C
4
C
5
C
6
Br Br
1 2 3 4
CH3 Br
5 6
CH3CCH2CH2CCH3 Br CH3
32
Chapter 1
NEL
Section 1.4
Example 1
Write the IUPAC name for CH3CH2CH2CH(Cl)CH2CH(Br)CH3.
Solution
This compound is 2-bromo-4-chloroheptane.
Example 2
Draw a structural diagram of 1,2-dichlorobenzene.
Solution
Cl Cl
Practice
Understanding Concepts
1. Draw structural diagrams for each of the following alkyl halides:
1,2-dichloroethane (solvent for rubber) tetrafluoroethene (used in the manufacture of Teflon) 1,2-dichloro-1,1,2,2-tetrafluoroethane (refrigerant) 1,4-dichlorobenzene (moth repellent)
(a) CHI3 (antiseptic) C CH2 Cl (b) CH2 CH3 (insecticide) (c) CH2Cl2 (paint remover) (d) CH2Br CHBr CH2Br (soil fumigant)
NEL
Organic Compounds
33
more polar than the less halogenated molecules, and thus have higher boiling points (Table 1). This difference in boiling points conveniently enables us to separate the components of a mixture by procedures such as fractional distillation.
Table 1 Boiling Points of Some Hydrocarbons and Corresponding Organic Halides Hydrocarbon CH4 C2H6 C3H8 C4H10 Boiling point (C) 164 89 42 0.5 Alkyl halide CH3Cl C2H5Cl C3H7Cl C4H9Cl Boiling point (C) 24 12 46 78
Figure 1 An ozone hole (blue) forms over the Antarctic every spring (September and October).
34
Chapter 1
Section 1.4
Practice
Understanding Concepts
3. Create a flow chart outlining the effects of an accidental leak of refrigerant from a
years.
5. (a) Write chemical equations predicting the decomposition of HCFCs and HFCs.
(b) Why might HCFCs and HFCs decompose more quickly than CFCs? (c) Why might this make them less damaging than CFCs?
EXPLORE an issue
Decision-Making Skills Define the Issue Analyze the Issue Identify Alternatives Defend the Position Research Evaluate
assessing cost and collect and sort information to help you decide whether the costs of automobile air conditioners are justified. (b) Select a role for yourselfsomeone who would be concerned about the kinds of costs that you have researched. Consider how this person might feel about the issue of air conditioning. (c) Role-play the meeting, with everyone taking a turn to put forward his/her position on whether the new car model should have air conditioning. (d) After the meeting, discuss and summarize the most important points made. If possible, come to a consensus about the issue.
GO
www.science.nelson.com
Br C H
1,2-dibromoethene
NEL
Organic Compounds
35
LEARNING
TIP
(b) H
Br C
Br C H + Br Br H
Br C Br
Br C Br H
Learning Tip
Several letter symbols are commonly used in general formulas to represent constituents of organic compounds: R represents any alkyl group R , R , etc. (R-prime, R-double prime) represent any alkyl group different from other Rs X represents any halogen atom represents a phenyl group
1,2-dibromoethene + bromine
1,1,2,2-tetrabromoethane
If we wanted to produce a halide of a benzene ring, we would need to arrange a substitution reaction with a halogen. The following example illustrates the chlorination of benzene in the presence of a catalyst. Further substitution can occur in the benzene ring until all hydrogen atoms are replaced by halogen atoms. Cl Cl
benzene
Cl
FeCl3 chlorobenzene
Cl
chlorine
hydrogen chloride
Alkyl halides can eliminate a hydrogen and a halide ion from adjacent carbon atoms, forming a double bond in their place, thereby becoming an alkene. The presence of a hydroxide ion is required, as shown in the example below. This type of reaction, in which atoms or ions are removed from a molecule, is called an elimination reaction. Elimination reactions of alkyl halides are the most commonly used method of preparing alkenes. H H C Br H C H
+ hydroxide ion
DID YOU
KNOW
C H
H + OH
Mustard Gas Mustard gas is a toxic alkyl halide that was used as a chemical weapon in World War I. When this compound is inhaled, it reacts rapidly with water molecules in the lungs, releasing HCl. The high concentrations of hydrochloric acid destroy lung tissue, leading to death. Mustard gas was banned in the 1980s as a result of international treaties, but nevertheless has been used since.
2-bromopropane
H H C
H C
H C H H + H O + Br H
+ water + bromide ion
propene
ClCH2
CH2
CH2
CH2Cl
SUMMARY
Preparation:
Organic Halides
Functional group: RX alkenes and alkynes organic halides addition reactions with halogens or hydrogen halides alkanes and aromatics organic halides substitution reactions with halogens or hydrogen halides Pathway to other groups: alkyl halides alkenes elimination reactions, removing hydrogen and halide ions
36 Chapter 1
NEL
Section 1.4
Practice
Understanding Concepts
6. Classify the following as substitution or addition reactions. Predict all possible prod-
ucts for the initial reaction only. Complete the word equation and the structural diagram equation in each case. You need not balance the equations. (a) trichloromethane chlorine (b) propene bromine (c) ethylene hydrogen iodide (d) ethane chlorine (e) Cl C C Cl F F (excess) H H H H (f)
C Cl Cl
C H
C H Cl
Cl
(g)
Extension
7. Why are some organic halides toxic while others are not? And why are some organ-
isms affected more than others? Use the Internet to find out, using the following key words in your search: bioaccumulation; fat soluble; food chain. Report on your findings in a short article for a popular science magazine or web site.
GO
www.science.nelson.com
Draw structural diagrams to represent the elimination reaction of 2-chloropentane to form an alkene. Include reactants, reaction conditions, and all possible products and their IUPAC names. lowing organic reactions: (a) propane chlorine 1-chloropropane 2-chloropropane hydrogen chloride (b) propene bromine 1,2-dibromopropane (c) benzene iodine iodobenzene hydrogen iodide
write a report or present one such case study. Examples of topics include: leaded and unleaded gasoline, use of solvents in dry cleaning, use of aerosol propellants, and use of pesticides and fertilizers.
5. Why was mustard gas such an effective weapon, both
during World War 1 and more recently? Research its properties and effects, and what defences have been developed against it.
GO
www.science.nelson.com
series of reactions, for example, some substitutions and some additions. (a) Plan a reaction beginning with a hydrocarbon to prepare 1,1,2-trichloroethane. (b) What experimental complications might arise in attempting the reactions suggested in part (a)? Making Connections
4. Research examples of the use of organic chemistry to
in the ozone layer and the release of chlorofluorocarbons, many manufacturers stopped using CFCs as propellants in aerosol cans. (a) Research what alternatives were developed, and the effectiveness of each in the marketplace. Are the alternatives still in use? Have any of them been found to cause problems? (b) Design a product (one that must be sprayed under pressure) and its packaging. Plan a marketing strategy that highlights the way in which your product is sprayed from the container.
GO
www.science.nelson.com
NEL
Organic Compounds
37