引用本文:
赵华绒, 吴百乐, 李秀玲, 秦敏锐, 蔡黄菊. 用Diels-Alder反应合成顺-4-环己烯-1,2-二羧酸及产品纯度分析——小综合实验推荐[J]. 大学化学,
2016, 31(8): 76-80.
doi:
10.3866/PKU.DXHX201511014
Citation: ZHAO Hua-Rong, WU Bai-Le, LI Xiu-Ling, QIN Min-Rui, CAI Huang-Ju. Preparation and Analysis of cis-Cyclohex-4-ene-1,2-dicarboxylic Acid via Diels-Alder Reaction: a Proposed Advanced Chemistry Experiment[J]. University Chemistry, 2016, 31(8): 76-80. doi: 10.3866/PKU.DXHX201511014
Citation: ZHAO Hua-Rong, WU Bai-Le, LI Xiu-Ling, QIN Min-Rui, CAI Huang-Ju. Preparation and Analysis of cis-Cyclohex-4-ene-1,2-dicarboxylic Acid via Diels-Alder Reaction: a Proposed Advanced Chemistry Experiment[J]. University Chemistry, 2016, 31(8): 76-80. doi: 10.3866/PKU.DXHX201511014
用Diels-Alder反应合成顺-4-环己烯-1,2-二羧酸及产品纯度分析——小综合实验推荐
摘要:
推荐了一个适合在化学及非化学专业开设的涉及有机合成、化学分析等操作的小综合实验。采用环丁烯砜加热分解释放出的丁二烯与顺丁烯二酸酐进行Diels-Alder反应来制备六元环化合物顺-4-环己烯-1,2-二酸酐，再经水解得到顺-4-环己烯-1,2-二羧酸。采用酸碱滴定法分析产品纯度，测定产物熔点，并通过红外光谱、核磁共振谱进行化合物结构表征。
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关键词:
- Diels-Alder反应
- / 顺-4-环己烯-1,2-二羧酸
- / 合成
- / 纯度分析
English
Preparation and Analysis of cis-Cyclohex-4-ene-1,2-dicarboxylic Acid via Diels-Alder Reaction: a Proposed Advanced Chemistry Experiment
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.
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