The Partitioning of Tetrahedral Intermediates
Predict the "partitioning" of the tetrahedral intermediate shown on the left, predicting which group around the central carbon is most likely to leave, and give the structure of the major organic product.Click the mouse on the intermediate to view the answer;
click on the pKa button to view approximate pKa values for the conjugate acids of the potential leaving groups.
In general, leaving group ability will parallel basicity, so that the most stable anion (formed from the strongest conjugate acid) will be the best leaving group (this is called a Bronsted relationship). In this intermediate, the chlorine (conjugate acid HCl) is a better leaving group than the phenolate anion (conjugate acid, phenol).
In general, leaving group ability will parallel basicity, so that the most stable anion (formed from the strongest conjugate acid) will be the best leaving group (this is called a Bronsted relationship).