1933 
The reactions of 1,3-butadiene are reasonably typical of conjugated dienes. The compound undergoes the usual reactions of alkenes, such as catalytic hydrogenation or radical and polar additions, but it does so more readily than most alkenes or dienes that have isolated double bonds. Furthermore, the products frequently are those of 1,2 and 1,4 addition:
Formation of both 1,2- and 1,4-addition products occurs not only with halogens, but also with other electrophiles such as the hydrogen halides. The mechanistic course of the reaction of 1,3-butadiene with hydrogen chloride is shown in Equation 13-1. The first step, as with alkenes, is formation of a carbocation. However, with 1,3-butadiene, if the proton is added to C1 (but not C2), the resulting cation has a substantial delocalization energy, with the charge distributed over two carbons due to type IV resonance. Attack of Cl⊖ as a nucleophile at one or the other of the positive carbons yields the 1,2- or the 1,4- addition product:
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