Chapter 10, Problem 10.46P

Interpretation Introduction

Interpretation:

Whether diazomethane is expected to react with a compound of formula ${\text{C}}_6{\text{H}}_{\text{12}}{\text{O}}_2$ with ${\text{pK}}_{\text{a}}\text{ = 25}$, is to be explained.

Concept introduction:

Diazomethane is a weak base that reacts only with moderately acidic species specifically carboxylic acids. The rate-determining step in this reaction is a proton transfer to diazomethane. Therefore, the reaction becomes unfavorable as the ${\text{pK}}_{\text{a}}$ value of the acidic species increases.