Dolbier HW Solutions 251

Dolbier HW Solutions 251 - 245 CONJUGATION IN ALKADIENES...

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vinyl cation for which two Lewis structures may be written. Capture of this cation gives the prod- ucts of 1,2 and 1,4 addition. The 1,2 addition product is more stable because of its conjugated sys- tem. The observations of the experiment tell us that the 1,4 addition product is formed faster, although we could not have predicted that. 10.32 ( a ) The two equilibria are: For ( E )-1,3-pentadiene: For ( Z )-1,3-pentadiene: ( b ) The s -cis conformation of ( Z )-1,3-pentadiene is destabilized by van der Waals strain involv- ing the methyl group. The equilibrium favors the s -trans conformation of ( Z )-1,3-pentadiene more than it does that
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