| Abstract: | The prototropic rearrangement of 3-phenyl-1-propenes to the corresponding 1-phenyl-1-propenes was investigated in basic media utilizing 0.1M sodium ethoxide in absolute ethanol at 81°C. It was found that the effect of substituents on the rate of such isomerizations follows the order: p-NO2 > o-Cl > m-Cl ≥ m-F > p-Br > o-CH3 > m-CH3 > m-CH(CH3)2 > p-CH(CH3)2 ≥ p-C(CH3)3 > o-OCH3. This is consistent with first-order kinetics and “BS ” mechanism. Quantitative treatment in terms of Hammett's equation showed a straight line, with a slope (p value) of +2.25. An increase in the strength of the base was also found to cause an increase in the rate of isomerization. |
