Search ECL

Browse ECL
Internet ResourcesACS ResourcesDemonstrationVisualizationData SetsProblem SetCourse Home PageModelingLabsCase StudiesTextbooksHome


Case Study in Environmental Chemistry....

Case Study 4: Kinetics of Carbaryl Hydrolysis

Author: Sarunya Hengpraprom and Cindy M.Lee, Environmental Engineering and Science, Clemson University.

For further detail choose the appropriate section

Hydrolysis mechanism for carbaryl

Acid-catalyzed hydrolysis is not an important mechanism for carbaryl because as a carbamate the central carbon atom is surrounded by two electron-withdrawing atoms (oxygen and nitrogen).  See Figure 3.  The protonation of the carboxyl oxygen would not greatly improve the appeal of the central carbon atom to a nucleophile. Very little research has been conducted on the neutral hydrolysis mechanism for carbamates, although it could be important at pH values found in the environment.

Alkaline hydrolysis is an important mechanism for carbaryl and other carbamates.  For carbaryl, which has hydrogen as the R1 substituent (see Figure 3), an elimination step is the slow step and determines the rate of hydrolysis.  For other carbamates that have an alkyl group as the R1 substituent, formation of a tetrahedral intermediate is the rate-determining step.  The alkyl group at R1 also makes the rate much slower than if hydrogen were present.