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Alkanes: Molecules Lacking Functional Groups
Alkanes: Molecules Lacking Functional Groups
Different blends of alkanes and other additives give rise to gasolines with different octane number ratings.
urn to page 90 of this book and look at the structures of the molecules illustrated in Problem 29. Each one contains a variety of types of bonds between various el-ements. Can we predict what kinds of chemical reactivity will be displayed by these substances? This chapter will begin to answer this question with a brief description of functional groups: the places in molecules where reactions tend to occur. Next we shall examine in depth the simplest class of organic molecules, the alkanes. If you have an appropriate kit, make a model of the structure shown at the top of this page. Does your model look exactly like the picture? Can it adopt other shapes by rotation of the atoms about bonds? This molecule is called 2,2,4-trimethylpentane, an alkane used in gasoline. As we proceed through this chapter, we shall explore the names,
physical properties, and structural mobility of the members of the alkane family.
52 Chapter 2 ALKANES
called alkanes. Molecules such as cyclohexane, whose carbons form a ring, are called cycloalkanes. Alkanes lack functional groups; as a result, they are relatively nonpo-lar and unreactive. The properties and chemistry of the alkanes are described in this chapter and in Chapters 3 and 4. Alkanes H2 C CH H2C H2C
C
2
CH
2
CH4
Methane
CH3OCH3
Ethane
CH3OCH2 OCH3
Propane
H2
Cyclohexane
Double and triple bonds are the functional groups of alkenes and alkynes, respec-tively. Their properties and chemistry are the topics of Chapters 11 through 13. Alkenes and Alkynes H
CH2 PCH2
Ethene (Ethylene) G
D
HCqCH
CH3OCqCH
CPCH2
Ethyne (Acetylene) Propyne
CH3
Propene
A special hydrocarbon is benzene, C6H6, in which three double bonds are incor-porated into a six-membered ring. Benzene and its derivatives are traditionally called aromatic, because some substituted benzenes do have a strong fragrance. Aromatic compounds are discussed in Chapters 15, 16, 22, and 25. Aromatic Compounds H H C C
C
H C C C H
Benzene
H C C
CH3 C C C C H
Methylbenzene (Toluene)
those in some ethers can be converted into a large variety of other functionalities and are therefore important in synthetic transformations. This chemistry is the subject of Chapters 8 and 9. Haloalkanes CH3Cl
Chloromethane (Methyl chloride)
Alcohols CH3CH2Cl
Chloroethane (Ethyl chloride)
Ethers CH3CH2OH
Ethanol
(Grain alcohol)
CH3OH
Methanol
(Wood alcohol)
CH3OCH3
Methoxymethane (Dimethyl ether)
(A refrigerant)
CH3CH2OCH2CH3
Ethoxyethane (Diethyl ether)
(An inhalation anesthetic)
(Topical anesthetics)
The carbonyl function, CPO, is found in aldehydes, in ketones, and, in con-junction with an attached OH, in thecarboxylic acids. Aldehydes and ketones are discussed in Chapters 17 and 18, the carboxylic acids and their derivatives in Chap-ters 19 and 20. Aldehydes O B HCH
Formaldehyde
(A disinfectant)
Ketones O B CH3CCH3
Propanone (Acetone)
O B CH3CH or CH3CHO
Acetaldehyde
(A hypnotic)
O B CH3CH2CCH3
Butanone (Methyl ethyl ketone)
(Common solvents)
Other elements give rise to further characteristic functional groups. For example, alkyl nitrogen compounds are amines. The replacement of oxygen in alcohols by sul-fur furnishes thiols. Amines H A CH3NCH3 or (CH3)2NH
N-Methylmethanamine (Dimethylamine)
(Used in tanning)
A Thiol
CH3NH2
Methanamine (Methylamine)
CH3SH
Methanethiol
(Excreted after we eat asparagus)