MT2-8 - 12(4 minutes 10 ngintg Answer the following a Which...

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Unformatted text preview: 12. (4 minutes, 10 ngintg! Answer the following: a. Which of the following represents the correct order of relative reactivities in a nucleophilic acyl substitution reaction? esters > acid anhydrides > acyl halides > amides acyl halides > acid anhydrides > esters > amt . es acid anhydrides > acyl halides > esters > amides acyl halides > esters > acid anhydrides > amides amides > carboxylic acids > acid anhydrides > acyl halides b. Which of the following statements best explains why protonation increases the rate of ester hydrolysis? The carbonyl carbon in the protonated ester is less positive than the carbonyl carbon in the unprotonated ester and therefore more susceptible to electrophilic attack, and the protonated leaving group is a stronger base. The carbonyl carbon in the protonated ester is more positive than the carbonyl carbon in the unprotonated ester and therefore more susceptible to nucleophilic attack, and the protonated leaving group is a stronger base. The carbonyl carbon in the protonated ester is less positive than the carbonyl carbon in the unprotonated ester and therefore more susceptible to nucleophilic attack, and the protonated leaving group is a weaker base. The carbonyl carbon in the protonated ester is more positive than the carbonyl carbon in the unprotonated ester and therefore more susceptible to nucleophilic attack, and the protonated leavin group is a weaker bas c. A carboxylic acid derivative will undergo a nucleophilic acyl substitution reaction provided that the incoming nucleophile is not a much stronger base than the substituent attached to the acyl group in the reactant. the substituent attached to the acyl group in the reactant is a very strong base. the incoming nucleophile is not a much weaker base than the substituent attached to the acyl group in reactant. the incoming nucleophile and the substituent attached to the acyl group in the reactant have similar basicities. the incoming nucleophile is not a much larger base than the substituent attached to the acyl group in the reactant. ...
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