Vol. 3, Issue 1, Part E (2017)

Abstract
The rate constants for the reaction of p-Toluenesulfonyl Chloride with α-Hydroxy acids in the presence of Pyridine in various polar aprotic, protic and nonpolar solvents have been investigated. The rate constants of the reaction are 3 – 50 times higher in polar aprotic solvents than in protic solvents. The solvent effects can be explained on the basis of solvation of anions in polar aprotic and protic solvents. The contributions of hydrogen bonding in solvation are discussed. Solvation of SN2 transition state anions depends on the nature of entering and leaving group. The transition state for these reactions is greatly solvated by methanol than Acetonitrile or DMF. Transition states for SN2 reactions of similar reactions respond in much similar way to the solvents.