Abstract
Abstract The rates of the reaction of acetophenone, ring-substituted acetophenones, propiophenone and isobutyrophenone with nitrous acid in 98.6% sulfuric acid have been measured by means of spectrophotometry. The rates have been expressed as ν=k [ketone] [NO+] with acetophenones and propiophenone, while they are ν=k [ketone] with isobutyrophenone. The electron-attracting groups in acetophenone accelerate the reaction with Hammett’s ρ value of +2.6. A probable mechanism has been suggested which involves a rate-determining nitrosation of enolized ketone for acetophenone and propiophenone, and a rate-determining enolization of ketone for isbutyrophenone.
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