The Electronic Conception of Valence And the Constitution of Benzene

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Ter 120 THE ELECTRONIC CONCEPTION OF VALENCE + Li . OH. In Holleman's formula for the ortho addition com- pound, the hydrogen atom of position 2 or 6 is eliminated with the hydroxyl radical of position I ; and in the para addition com- pound the hydrogen atom of position 4 is likewise eliminated with hydroxyl of position I. Since the elimination of water is the + union of H and OH, it follows that the hydrogen atoms of positions 2, 4, and 6 of the ortho and para nitro-compounds of Holleman are ...positive. Consequently, from the symmetry standpoint, the hydrogen atoms or substituents of position I, 3, and 5 are negative. As a matter of fact, the ortho and para nitro-compounds, in which X = Cl or Br, readily exchange X for hydroxyl on treatment with aqueous potassium hydroxide ; since OH is negative, X is accordingly negative.
Having correlated Holleman's ortho and para compounds with the electronic formulae, consider, on the other hand, his formula for the meta addition compound. Here, HO unites + with the free valences of carbon 'atoms 2 or 6, while NO 2 com- bines with those of atoms 3 or 5.


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