Organic Chemistry

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The three chaptersin Part III discuss

the reactions of compounds that have an

electron-withdrawing atom or group—a

potential leaving group—bonded to an

hybridized carbon. These compounds

can undergo substitution and/or elimina-

tion reactions.

Chapter 10discusses the substitution reactions of alkyl
halides. Of the different compounds that undergo substi-
tution and elimination reactions, alkyl halides are exam-
ined first because they have relatively good leaving
groups. You will also see the kinds of compounds biolog-
ical organisms use in place of alkyl halides, since alkyl
halides are not readily available in nature.

Chapter 11covers the elimination reactions of alkyl
halides. Because alkyl halides can undergo both substitu-
tion and elimination reactions, this chapter also discusses
the factors that determine whether a given alkyl halide
will undergo a substitution reaction, an elimination reac-
tion, or both substitution and elimination reactions.

Chapter 12 discusses compounds other than alkyl
halides that undergo substitution and elimination reac-
tions. You will see that because alcohols and ethers have
relatively poor leaving groups compared with the leaving
groups of alkyl halides, alcohols and ethers must be acti-
vated before the groups can be substituted or eliminated.
Several methods commonly used to activate leaving
groups will be examined. The reactions of thiols and sul-
fides will be compared with those of alcohols and ethers.
By looking at the reactions of epoxides, you will see how
ring strain can affect leaving ability. You will also see
how the carcinogenicity of arene oxides is related to car-
bocation stability. Finally, this chapter will introduce you
to organometallic compounds, a class of compounds that
is very important to synthetic organic chemists.

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3

Substitution

and Elimination

Reactions

PART THREE

Chapter 10

Substitution Reactions

of Alkyl Halides

Chapter 11

Elimination Reactions of Alkyl

Halides; Competition Between

Substitution and Elimination

Chapter 12

Reactions of Alcohols,

Ethers, Epoxides, and

Sulfur-Containing Compounds •

Organometallic Compounds