1) Nucleophilic attack on the carbonyl. The LibreTexts libraries are Powered by MindTouch® and are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. 1H-benzo[4,5]cyclohepta[1,2-c]furan-1,3,4-trione, 3-(3,5-dimethoxybenzyl)dihydro-2,5-furandione, 3-methyl-3-veratryl-tetrahydrofuran-2,5-quinone, 3,4-diisopropylidene-tetrahydro-furan-2,5-dione, 5,6,7,8-tetrahydro-1H-cyclohepta[c]furan-1,3(4H)-dione, 1,1,5,5-tetramethyl-1,5-dihydro-3-benzoxepine-2,4-dione, 7-phenyl-4,5,8,8a-tetrahydro-1H-cyclohepta[c]furan-1,3(3aH)-dione, acetic 2-anilino-2-phenylpropanoic anhydride, 5,7-diethoxy-3a,4-dihydro-2-benzofuran-1,3-dione, 3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione, 7-methoxy-4,6,7,7a-tetrahydro-3aH-isobenzofuran-1,3,5-trione, 5,5-dimethyl-4,5-dihydro-2-benzoxepine-1,3-dione, 3,4-Dihydro-1,2-naphthalenedicarboxylic anhydride, 3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1,3-dione, 4,6-dimethoxy-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione, 7H-[1,3]dioxolo[4,5-h]isochromene-7,9(6H)-dione, (3Z)-3-[(benzylamino)methylene]-2H-pyran-2,6(3H)-dione, methyl 1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2-benzofuran-5-carboxylate, 1,3-dioxo-1,3-dihydro-2-benzofuran-5-carbonyl chloride, 4-acetyl-6-chloro-1H,3H-benzo[de]isochromene-1,3-dione, 5,6-bis(chloromethyl)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione, 1,3-dioxo-1,3-dihydro-2-benzofuran-4-carbaldehyde dimethylhydrazone, (3E)-3-(1-naphthylmethylene)dihydro-2,5-furandione, 4-(4-methylphenoxy)-2-benzofuran-1,3-dione, 3,3,4,4,5,5-hexamethyl-tetrahydro-pyran-2,6-dione, 5-chloro-4,6,7-trimethyl-2-benzofuran-1,3-dione, 4-anilino-5,7-diethyl-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione, 3-isopropylidene-tetrahydro-furan-2,5-dione, furo[3,4-c]pyrrolo[1,2-a]quinoline-1,3-dione, 3a,4,8,8a-tetrahydro-1H,3H-thieno[3,4-f][2]benzofuran-1,3-dione, 5,6,7,8-tetramethyl-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1,3-dione. Some cyclic anhydrides can be synthesized from the corresponding dicarboxylic acid with gentle heating. G. Bartoli, M. Bosco, A. Molecular Formula: C 13 H 6 O 4; Molecular Weight: 226.188 g/mol; Cas Number:- ... acetic 2-anilino-2-phenylpropanoic anhydride. General mechanism. Acid chlorides react with carboxylic acids to form anhydrides as shown in the reaction below. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. Acid anhydrides - Synthesis and Properties. For more information contact us at info@libretexts.org or check out our status page at https://status.libretexts.org. Although aldehydes and ketones also contain a carbonyl their chemistry is distinctly different because they do not contain a suitable leaving group. Although there are many types of carboxylic acid derivatives known we will be focusing on just four: Acid halides, Acid anhydrides, Esters, and Amides.

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