Upenn Diels-Alder Reaction and Hydrolysis Prelab

Pre-Lab 6 Part #1

Expt#6

Date: 07/06/10 TA: Scott

Diels-Alder Reaction and Hydrolysis

Introduction

Diels-Alder reaction of 1,3-butadiene and maleic anhydride will produce cyclohexene-cis-1,2-dicarboxylic anhydride. The product will be hydrolyzed to the diacid. Both the anhydride and the diacid will be tested via melting point determination and unsaturation tests (bromine test and Baeyer test). The purpose of this experiment is to conduct diels alder reaction and subsequent hydrolysis.

Main Reaction and Mechanism

Diels-Alder reaction:

Hydrolysis:

Table of Reactants

Diels-Adler Reaction:

Compound | Structure | Molt. Wt.(g/mol) | Theoretical Amounts Used(ml) grams | Moles used required | Theoretical physical properties |

| | | ml | grams | used | required | |

1,3-butadiene | 2 | 54.0914 | - | 1.25 | 0.0231 | 0.0153 | Colorless gas |

maleic anhydride | 3 | 98.058 | - | 1.5 | 0.0153 | 0.0153 | Colorless, white solid with penetrating odor, causes burns |

Petroleum ether | - | - | ~5 | 3.28 | - | - | b.p. = 60-80℃density = 0.656g/ml |

Xylene | | 318.501 | 11 | 9.48 | - | - | Water insolubleSolvent for reactionb.p.=140℃density- 0.862g/ml |

3-sulfolene | 1 | 118.150 | - | 2.5 | 0.0211 | 0.0153 | White, pale yellow crystal |

Limiting reagent = maleic anhydride

Hydrolysis Reaction:

Compound | Structure | Molt. Wt.(g/mol) | Theoretical Amounts Used(ml) grams | Moles used required | Theoretical physical properties |

| | | ml | grams | used | required | |

cyclohexene-cis-1,2-dicarboxylic anhydride | 4 | 152.088 | - | 2.75 | 0.0181 | 0.0181 | m.p.=103-104℃ |

H2O | - | 18.0 | - | excess | - | - | - |

Limiting reagent = anhydride

Table of Products

Compound | Structure | Molt. Wt.(g/mol) |...