a) The pKa of p-chlorobenzoic acid is 3.98; that of benzoic acid is 4.19.
i)
Calculate σ for p-Cl.
b) If ρ value for the alkaline saponification of methyl esters of substituted benzoic acids is 2.38, and the rate constant for saponification of methyl benzoate under the conditions of interest is 2.0 x 10-4
L mol-1 s-1, Calculate the rate constant of methyl m-nitrobenzoate.
c) Match the ρ values with the appropriate reactions. Explain your reasoning.
Reaction constants: + 2.45, +0.75, -2.3`9, -7.29
Reactions are:
i)
Nitration of substituted benzenes
ii)
Ionization of substituted benzenthiols
iii)
Ionization of substituted benzenephosphonic acids
iv)
Reaction of substituted N,N-dimethylaniline with methyl iodide
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