Carboxylic Acid Derivative Reactions | Summary and Q&A

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April 18, 2021
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Carboxylic Acid Derivative Reactions

TL;DR

Acid chlorides are the most reactive, followed by acid anhydrides, esters, amides, and carboxylate ions. Reactions with water produce carboxylic acids, with acid chlorides and acid anhydrides producing two carboxylic acids. The reactions can be driven forward by adjusting reactant concentrations or using heat as a dehydrating reagent.

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Questions & Answers

Q: Which acid derivative is the most reactive?

Acid chlorides are the most reactive among carboxylic acid derivatives.

Q: What happens when water reacts with acid chlorides?

Water reacts with acid chlorides to produce carboxylic acids, with the byproduct being hydrogen chloride.

Q: How can the reaction between acid anhydrides and water be driven forward?

The reaction can be driven forward by adding heat or a dehydrating reagent, which decreases the concentration of water.

Q: How are anhydrides formed from acid chlorides and carboxylic acids?

Anhydrides can be formed by reacting acid chlorides with carboxylic acids, with the byproduct being hydrogen chloride.

Summary & Key Takeaways

  • Acid chlorides are more reactive than acid anhydrides, which are more reactive than esters. Carboxylic acids and esters have similar reactivity, while amides are less reactive than esters.

  • Adding water to acid chlorides or acid anhydrides produces carboxylic acids, with acid anhydrides producing two carboxylic acids. The reactions favor the formation of carboxylic acids due to the lower reactivity of the product.

  • The reaction between acid chlorides and water involves water attacking the carbonyl group, forming a tetrahedral intermediate. A weak base, such as another water molecule, removes a hydrogen, and the leaving group, chloride, is expelled to form the carboxylic acid.

  • Acid anhydrides can be formed by removing water from two carboxylic acid molecules. Adding heat or a dehydrating reagent drives the reaction forward by decreasing the concentration of water.

  • Anhydrides can also be formed by reacting acid chlorides with carboxylic acids. The reaction is favorable as hydrogen chloride is a gas and leaves the solution, decreasing the concentration of the product.

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