Kinetic Study on Solvolysis of 2‐Methylfuran‐3‐carbonyl Chloride in Binary Solvent Mixtures

Rate constants for solvolysis of 2‐methylfuran‐3‐carbonyl chloride ( 1 ) in ethanol, methanol, and aqueous binary mixtures incorporating ethanol, methanol, acetone, 2,2,2‐trifluoroethanol, and 1,1,1,3,3,3‐hexafluoro‐2‐propanol are reported. The 34 solvents give an extended Grunwald–Winstein correlation with l = 0.26 ± 0.05, m = 0.71 ± 0.04, and correlation coefficient R 2 = 0.963. Activation parameters calculated from the rate constants measured at three different temperatures in five different solvents are presented. In the deuterated methanol, a solvent kinetic isotope effect of 1.15 was observed at 0°C. The kinetic features observed indicate that the reaction proceeds through an S N 1 mechanism with a little S N 2 character. The reactivity–selectivity principle is also followed in alcohol‐water mixtures.