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Extra resources for Organic Chemistry II
Figure 3-1 illustrates the effect of electronegativity differences on bond polarity. C δ+ X δ− Figure 3-1 Electrons in the overlap region between the carbon and the halogen atoms are attracted to the more electronegative halogen atom. The carbon atom, which now has less of a share of the bonding electrons, becomes partially positive, and the halogen atom, which has a greater share of these electrons, becomes partially negative. Remember that a nucleophile is a substance that has a pair of electrons that it can donate to another atom.
NO2 H NO2 + + + H ORGANIC CHEMISTRY II 21 REACTIONS OF AROMATIC COMPOUNDS The sulfonation of benzene The reaction of benzene with concentrated sulfuric acid at room temperature produces benzenesulfonic acid. SO3H 25ϒ + H2SO4 The mechanism for the reaction that produces benzenesulfonic acid occurs in the following steps: 1. The sulfuric acid reacts with itself to form sulfur trioxide, the electrophile. + − SO3 + H3O + HSO4 2 H2SO4 This reaction takes place via a three-step process: a. 22 H2SO4 + − H + HSO4 CLIFFSQUICKReview REACTIONS OF AROMATIC COMPOUNDS b.
In the Birch reduction, benzene, in the presence of sodium metal in liquid ammonia and methyl alcohol, produces a nonconjugated diene system. This reaction provides a convenient method for making a wide variety of useful cyclic dienes. H H H H Na NH3 CH3OH The production of the less stable nonconjugated diene instead of the more stable conjugated diene occurs because the reaction is kinetically controlled rather than thermodynamically controlled. In general, reactions that aren’t easily reversible are kinetically controlled because equilibrium is rarely established.