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 E-mail:zhr0103@zju.edu.cn
  • Supported by:
    浙江省2013年高等教育课堂教学改革项目(kg2013005);浙江大学2015年探究性实验教学改革项目

Abstract:

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

MSC2000: 

  • O6