Problems with Chlorination

From WikidChem

Dualistic radical theory insisted that radicals either have a positive or negative charge character (they were not talking ions that could move around independently - JMM). However, in the case of C7H5O-H, both the radicals C7H5O and H have positive charges. So they should fly apart according to Coulomb's law (not exactly, because not ions, they should just not constitute a compound - it's hard to put ourselves in their mental shoes - JMM). Dualistic theory runs into problems.

An alternative theory is the substition/unitary/type theory.

The ball at the Tuileries palace was interrupted due to fumes from the candles. Dumas suspects the problem to be the result of bleaching the candle wax. Organic compounds can apparently fix (i.e. grab hold of) chlorine.

When chlorine is added to an alkene, the double bond becomes a single bond, and each of the atoms originally connected by the double bond forms a bond with one of the chlorine atoms. This occurs because Cl2 has a low LUMO and CH2=CH2 has a high HOMO. First, the chlorine dimer breaks during attack by the alkene, and one Cl atom forms a cyclocation-structure with the CH2=CH2 (called "chloronium"). Then the other chlorine comes and reacts with the temporary, or "intermediate", structure to form Cl-CH2-CH2-Cl.