(a) The resonance structures shown in part (a) of Fig. P22.76 can be written for an

Chapter 22, Problem 22.74

(choose chapter or problem)

(a) The resonance structures shown in part (a) of Fig. P22.76 can be written for an a,b-unsaturated carboxylic acid. Would this type of resonance interaction increase or diminish the acidity of an a,b- unsaturated carboxylic acid relative to that of an ordinary carboxylic acid? Explain. (b) Consider the pKa data given in part (b) of Fig. P22.76. Show how these data are consistent with both the polar effect of the double bond and the resonance effect in part (a).

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