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  Alkyl Halides General Reactivity Homework Help - K-12 Grade Level, College Level Chemistry

Introduction to Alkyl Halide General Reactivity

A carbon-halogen bond is the functional group of alkyl halides, the general halogens being fluorine, iodine, chlorine, and bromine. By the exception of iodine, these halogens have electronegativities considerably greater than carbon. Subsequently, this functional group is polarized thus that the carbon is electrophilic and the halogen is nucleophilic, as displayed in the diagram. Two features other than electronegativity also have a significant effect on the chemical behaviour of these compounds. The 1st of these is covalent bond strength. Strongest of the carbon-halogen covalent bonds is that to fluorine. Surprisingly, this is the strongest general single bond to carbon, being than a carbon-carbon bond, approximately 30 kcal/mole stronger and about 15 kcal/mole stronger than a carbon-hydrogen bond. Due to this, fluorocarbons and alkyl fluorides generally are chemically and thermodynamically quite stable and do not distribute any of the reactivity patterns displayed by the other alkyl halides.

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The carbon-chlorine covalent bond is little weaker than a carbon-carbon bond, and the bonds to another halogens are weaker yet, the bond to iodine being about 33% weaker. The second factor to be referred is the relative stability of the corresponding halide anions, which is probably the type in which these electronegative atoms will be replaced. From the relative acidities of the H-X acids, this stability might be estimated, presuming that the strongest acid releases the most stable conjugate base (halide anion). With the exception of HF (pKa = 3.2), all hydrohalic acids are very strong, small variations being in the direction HCl < HBr < HI.

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