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.

2-1 Functional Groups: Centers of Reactivity

Many organic molecules consist predominantly of a backbone of carbons linked by single bonds, with only hydrogen atoms attached. However, they may also contain doubly or triply bonded carbons, as well as other elements. These atoms or groups of atoms tend to be sites of comparatively high chemical reactivity and are referred to as functional groups or functionalities. Such groups have characteristic proper-ties, and they control the reactivity of the molecule as a whole.

Hydrocarbons are molecules that contain only hydrogen and carbon

We begin our study with hydrocarbons, which have the general empirical formula Cx Hy. Those containing only single bonds, such as methane, ethane, and propane, are
51

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)

Many functional groups contain polar bonds

Polar bonds determine the behavior of many classes of molecules. Recall that polar-ity is due to a difference in the electronegativity of two atoms bound to each other (Section 1-3). Chapters 6 and 7 will introduce the haloalkanes, which contain polar carbonhalogen bonds as their functional groups. Another example is thehydroxy group, OH, characteristic ofalcohols. The characteristic functional unit of ethers is an oxygen atom

bonded to two carbon atoms. The functional group in alcohols and

2-1 Functional Groups: Centers of Reactivity 53

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)

Carboxylic Acids O B HCOH or HCOOH or HCO2H

Formic acid
(Strong irritant)

(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

O B CH3COH or CH3COOH or CH3CO2H

Acetic acid
(In vinegar)

CH3NH2
Methanamine (Methylamine)

CH3SH
Methanethiol
(Excreted after we eat asparagus)

R represents a part of an alkane molecule

Table 2-1 depicts a selection of common functional groups, the class of to which they give rise, a general structure, and an example. In the general we commonly use the symbol R (for radical or residue) to represent an alkyl a molecular fragment derived by removal of one hydrogen atom from an alkane tion 2-3). Therefore, a general formula for a haloalkane is RX, in which R for any alkyl group and X for any halogen. Alcohols are similarly represented RO H. In structures that contain multiple alkyl groups, we add a prime9) ( ble prime (0) to R to distinguish groups that differ in structure from one another. Thus aThe alkanes C29H60 general formula for an ether in which both alkyl groups are the same (a symmet-ricaland C31H64 ether) is ROR, whereas an ether with two dissimilar groups (anunsymmet-ricalconstitute the waxy, water-repellent ether) is represented by RO9R.
coatings on these wild lupine leaves.

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