Textbook Question
Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.
(c) isobutylamine → N-isobutylformamide
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22. Carboxylic Acid Derivatives: NAS
Nucleophilic Acyl Substitution
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Determine the major product for the following reaction.
A
B
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D
Verified step by step guidance1
Identify the reactants: The reaction involves a carboxylic acid (propanoic acid) and a cyclic alcohol (cyclopentanol) in the presence of an acid catalyst (H+).
Recognize the type of reaction: This is an esterification reaction, where a carboxylic acid reacts with an alcohol to form an ester and water.
Protonation of the carboxylic acid: The acid catalyst (H+) protonates the carbonyl oxygen of the carboxylic acid, increasing the electrophilicity of the carbonyl carbon.
Nucleophilic attack by the alcohol: The hydroxyl group of cyclopentanol attacks the electrophilic carbonyl carbon, forming a tetrahedral intermediate.
Formation of the ester: The intermediate collapses, expelling a water molecule and forming the ester linkage between the carboxylic acid and the alcohol, resulting in the major product, an ester.
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