Textbook Question
Write a mechanism for each of the following reactions:
b. the aminolysis of phenyl formate, using methylamine.
22. Carboxylic Acid Derivatives: NAS
Nucleophilic Acyl Substitution
7:33 minutesProblem 46a
Textbook Question
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 guidance1
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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7mKey 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.
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Anhydride Nomenclature
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.
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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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