The reactivity of carboxylic acids and derivatives toward nucleophiles is similar to the reactivity of aldehydes and ketones. The carbonyl carbon possesses a partial positive charge due to the polarity of the carbon-oxygen bond. There is also the contribution of a resonance form which introduces a partial positive charge to the carbon, making it susceptible to attack by nucleophiles. Furthermore, protonation of the carbonyl portion of the carboxyl group under conditions of acid catalysis (which also can occur with aldehydes and ketones), increases the susceptibility of the group toward attack by the nucleophile. Acyl transfer reactions as a class begin by formation of a tetrahedral intermediate which generally resolves by an elimination step that restores the carbonyl group. Addition-elimination has occurs with the original group bound to the carbonyl portion having been substituted by another. The acyl transfer mechanism of addition-elimination among the carboxylic acid derivatives is one of the most important in chemistry.












The WikiPremed MCAT Course is a comprehensive course in the undergraduate level general sciences. Undergraduate level physics, chemistry, organic chemistry and biology are presented by this course as a unified whole within a spiraling curriculum. Please read our policies on Privacy and Shipping & Returns.  Contact Us. MCAT is a registered trademark of the Association of American Medical Colleges, which does not endorse the WikiPremed Course. WikiPremed offers the customers of our publications or our teaching services no guarantees regarding eventual performance on the MCAT.


Creative Commons License
WikiPremed is a trademark of Wisebridge Learning Systems LLC. The work of WikiPremed is published under a Creative Commons Attribution NonCommercial ShareAlike License. There are elements of work here, such as a subset of the images in the archive from WikiPedia, that originated as GNU General Public License works, so take care to follow the unique stipulations of that license in printed reproductions.