Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook

Bruice 8th Edition

Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Problem 46a

Chapter 16, Problem 46a

Propose a mechanism for the formation of succinic anhydride from succinic acid in the presence of acetic anhydride at neutral pH.

Verified step by step guidance

Identify the functional groups in succinic acid and acetic anhydride. Succinic acid contains two carboxylic acid groups (-COOH), while acetic anhydride is a reactive anhydride that can act as an acylating agent.

Recognize the role of acetic anhydride in the reaction. Acetic anhydride reacts with one of the carboxylic acid groups of succinic acid to form an intermediate mixed anhydride. This step involves nucleophilic attack by the carboxylate oxygen of succinic acid on the carbonyl carbon of acetic anhydride, followed by the departure of an acetate ion.

Propose the cyclization step. The second carboxylic acid group of succinic acid acts as a nucleophile, attacking the carbonyl carbon of the mixed anhydride intermediate. This intramolecular nucleophilic acyl substitution leads to the formation of a five-membered ring structure, which is succinic anhydride.

Account for the neutral pH condition. At neutral pH, the reaction proceeds without the need for additional acid or base catalysts because acetic anhydride is sufficiently reactive to facilitate the formation of the mixed anhydride and subsequent cyclization.

Conclude the mechanism by noting the byproduct. The reaction releases acetic acid as a byproduct when the acetate ion from acetic anhydride combines with a proton from the reaction intermediates.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Carboxylic Acids and Anhydrides

Carboxylic acids, like succinic acid, contain a carboxyl group (-COOH) that can undergo dehydration to form an anhydride. Anhydrides are formed when two carboxylic acid molecules lose a water molecule, resulting in a compound with two acyl groups. Understanding the structure and reactivity of these functional groups is essential for proposing a mechanism for the transformation.

Nucleophilic Acyl Substitution

Nucleophilic acyl substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks the carbonyl carbon of an acyl compound, leading to the substitution of a leaving group. In the case of succinic acid and acetic anhydride, the hydroxyl group of succinic acid can be replaced by an acetic group, facilitating the formation of succinic anhydride. This concept is crucial for understanding how the reaction proceeds.

Dehydration Reactions

Dehydration reactions involve the removal of water from a molecule, often leading to the formation of a double bond or a cyclic structure. In the context of succinic acid and acetic anhydride, the dehydration step is key to forming succinic anhydride, as it involves the elimination of water during the reaction. Recognizing the role of dehydration in organic transformations is vital for grasping the proposed mechanism.

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Related Practice

Textbook Question

How could you synthesize the following compounds starting with a carboxylic acid?

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Textbook Question

Draw a structure for each of the following:

a. N,N-dimethylhexanamide

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Textbook Question

Propose a mechanism for the reaction of acetic anhydride with water.

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Textbook Question

How does acetic anhydride make it easier to form the anhydride?

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Textbook Question

We saw that acid anhydrides react with alcohols, water, and amines. In which of these reactions can the tetrahedral intermediate eliminate the carboxylate ion even if it does not lose a proton before the elimination step? Explain.

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Textbook Question

Which alkyl halides form the carboxylic acids listed here after reaction with sodium cyanide followed by heating the product in an acidic aqueous solution?

a. butyric acid

b. isovaleric acid

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