RELATIVE REACTIVITIES OF METHANOL AND METHOXIDE ION IN ADDITION TO 4-CHLOROBENZYNE

The relative reactivities of CH3O- and CH3OH toward 4-chlorobenzyne can be reckoned from the variation of the chloroanisole para/meta ratio with NaOCH3 concentration. The necessary mathematical expression is derived, and a set of experimental determinations gives the expected linear plot. Methoxide ion is estimated to be 157 times as reactive as methanol toward the carbon in 4-chlorobenzyne meta to chlorine, and 70 times as reactive toward the position para to chlorine. © 1969, American Chemical Society. All rights reserved.