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Rank the carboxylic acid derivative in order of increasing reactivity towards hydrolysis (most reactive on the right)

a. Acid chloride < Ester < Amide < Carboxylic acid
b. Ester < Acid chloride < Amide < Carboxylic acid
c. Amide < Ester < Acid chloride < Carboxylic acid
d. Carboxylic acid < Amide < Ester < Acid chloride

User Jeriho
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1 Answer

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Final answer:

The correct order of reactivity towards hydrolysis for carboxylic acid derivatives from least to most reactive is amide < carboxylic acid < ester < acid chloride, reflecting factors such as the ability of the leaving group and resonance stabilization.

Step-by-step explanation:

To rank carboxylic acid derivatives in order of increasing reactivity towards hydrolysis, recalling the reactivity order is crucial. The order for carboxylic acid derivatives, most stable to least stable (which correlates with least reactive to most reactive towards hydrolysis), is as follows: amides < carboxylic acids < esters < acid chlorides. Hence, by this order, the correct ranking from least reactive to most reactive towards hydrolysis (most reactive on the right) is:

  • Amide < Carboxylic acid < Ester < Acid chloride

This matches with the reactivity order because of factors such as the strength of the leaving group and the stability of the intermediate. Acid chlorides, with the best leaving group (chloride ion), react most readily, while amides, with poor leaving groups and resonance stabilization, are the least reactive.

User Steward
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