Illustrative of their alkylating activity are reactions with potassium iodide in acetone, chloroacetone reacts faster than 1-chloropropane by a factor of 36,000. Halo ketones react with phosphites in the Perkow reaction.
The halo group can be removed in reductive dehalogenation of halo ketones. α-Halo ketones can also be converted to alkenes by treatment with hydrazine.
Due to the presence of two electron withdrawing groups (carbonyl and halide), the α-hydrogen is acidic. This property is exploited in the Favorskii rearrangement, where base abstracts first an acidic α-hydrogen and the resulting carbanion then displaces the halogen.
In crossed aldol reactions between halo ketones and aldehydes, the initial reaction product is a halohydrin which can subsequently form an oxirane in the presence of base.
α-Halo ketones can react with amines to form an α-halo imine, which can be converted back to the parent halo ketone by hydrolysis, so that halo imines may be used as masked versions of halo ketones. This allows some chemical transformations to be achieved that are not possible with the parent halo ketones directly.