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Reactivity

The reactivity of alcohols can be understood by examining the electron distribution within the C-OH group. It is similar to that of the haloalkanes, but the result is very different. Why?

In an alkyl halide the carbon is electrophilic and electron deficient and is attacked by nucleophiles, because the halide is a good leaving group

Alkyl Halide

The halogen atom is very electronegative and heavily polarizes the C-X bond.

Furthermore, the halide is a very good leaving group and can be expelled by a good nucleophile.

This does not happen with alcohols.

In the alcohol, the electron-deficient carbon is not attacked by nucleophiles because hydroxide is a very bad leaving group; the OH hydrogen is weakly acidic

Alcohol

The electronegative oxygen polarizes the C-O bond in a similar way the halogen does.

But, unlike the halide, the hydroxide is an extremely bad leaving group.

Hence, alcohols don't directly react with nucleophiles.

In addition, alcohols display acidity, a property not shown by the corresponding halides. The weak acidity of the OH group makes alcohols give reactions not possible with the alkyl halides.