University Chemistry ›› 2016, Vol. 31 ›› Issue (8): 76-80.doi: 10.3866/PKU.DXHX201511014

• Chemistry Laboratory • Previous Articles     Next Articles

Preparation and Analysis of cis-Cyclohex-4-ene-1,2-dicarboxylic Acid via Diels-Alder Reaction: a Proposed Advanced Chemistry Experiment

Hua-Rong ZHAO*(),Bai-Le WU,Xiu-Ling LI,Min-Rui QIN,Huang-Ju CAI   

  • Published:2016-08-31
  • Contact: Hua-Rong ZHAO
  • Supported by:


An advanced chemistry experiment involving organic synthesis and chemical analysis is proposed. This experiment is suitable for both chemistry major and non-chemistry major students. ciscyclohex-4-ene-1,2-dicarboxylic acid can be prepared by Diels-Alder reaction with 1,3-butadiene generated readily in situ by means of chelotropic extrusion of sulfur dioxide from 2,5-dihydrothiophene-1,1-dioxide. The Diels-Alder adduct formed in this instance is readily hydrolysed to the dicarboxylic acid by heating with water. The purity of product is analyzed using acid-base titration, and the structure of product is characterized by M.P., IR and 1H NMR.

Key words: Diels-Alder reaction, cis-Cyclohex-4-ene-1,2-dicarboxylic acid, Synthesis, Purity analysis


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