PART 2. MONOFUNCTIONAL ORGANIC COMPOUNDS OF BIOLOGICAL INTERESTS.

Chapter 7. ORGANIC HALIDES, ALCOHOLS, PHENOLS, ETHERS, AMINES, AND ORGANOSULFUR COMPOUNDS

Organic halides are hydrocarbon derivatives in which one or more halogen at oms replace hydrogen atom(s).

In this section the main attention will be paid to alkyl halides in which a halogen is attached to saturated, sp³-hybridized carbon. Other types of organic halides, such as aryl halides and vinyl halides, RCH=CHHal, also exist. Halogen in these compounds is bonded to sp²-hybridized carbon, therefore they differ greatly in their chemistry from alkyl halides.

Before discussing the chemistry of alkyl halides, let us consider reactive sites in a structure of the saturated compound of the general formula R-X, where × is an electron-withdrawing group. Polarization of a C-X bond results in the formation of an electrophilic site (the α carbon) that can be attacked by a nucleophilic reagent. The bonds C_a-C_β and C_β-H are also polarized due to the -/ effect of a substituent X. This results in the formation of CH-acidic site that can react with bases.

Both sites define the reactivity of the compound. They will be discussed below.