Vernier Software and Technology
Vernier Software & Technology

The Diels-Alder Reaction of Anthracene with Maleic Anhydride

Introduction

The Diels-Alder reaction is a member of a class of reactions called cycloadditions. The reaction involves three π bonds, two from the diene and one from the dienophile in a concerted reaction to form a six-membered ring. Since the reaction involves four π electrons in the diene and two π electrons from the dienophile, it is sometimes referred to as a 4 + 2 cycloaddition.

Normal Diels-Alder reactions are favored by electron donating groups on the diene and electron withdrawing groups on the dienophile. The diene must be capable of achieving an s-cis conformation to generate the cis double bond in the cyclohexene product. Acyclic dienes may rotate around a single bond, but dienes locked in the s-trans conformation do not react.

The purpose of this experiment is to form 9,10-dihydroanthracene-9,10-α,β-succinic anhydride by way of a Diels Alder reaction between anthracene and maleic anhydride, as shown in the reaction below. Anthracene acts as the diene and maleic anhydride functions as the dienophile. Xylene (dimethylbenzene) is used as a high boiling temperature solvent so that the reaction will proceed quickly. Melting temperature analysis will be used to characterize the product.

Objectives

In this experiment, you will

  • Synthesize 9,10-dihydroanthracene-9,10-α,β-succinic anhydride.
  • Isolate the product.
  • Measure the melting temperature of your product.

Sensors and Equipment

This experiment features the following Vernier sensors and equipment.

Option 1

Option 2

Additional Requirements

You may also need an interface and software for data collection. What do I need for data collection?

Organic Chemistry with Vernier

See other experiments from the lab book.

1Determining Melting Temperature
2Recrystallization of Benzoic Acid and Aspirin
3Determination of a Boiling Point: Simple and Fractional Distillation
4Identifying an Unknown Analgesic by Melting Temperature and Thin-Layer Chromatography
5Separation of Organic Compounds by Acid-Base Extraction Techniques
6Understanding Polarimetry
7Identification of Organic Unknowns Using Polarimetry
8Investigating Gas Chromatography
9Fractional Distillation of Esters
10Understanding Intermolecular Forces Using a Gas Chromatograph: Enthalpy of Vaporization
11Investigating Thermodynamic Relationships of Substituted Hydrocarbons
12Extraction of Spinach Pigments and Analysis by Electronic Absorption Spectroscopy
13SN1: Synthesis of t-butyl chloride
14SN2: Synthesis of 1-bromobutane
15Observing the Reaction Kinetics of Sucrose with Polarimetry
16The Synthesis and Analysis of Aspirin
17Isolation and Epoxidation of a Natural Product: Limonene
18Synthesizing Ethyl Acetate by Fisher Esterification
19Synthesis of Dibenzalacetone by Aldol Condensation
20The Diels-Alder Reaction of Anthracene with Maleic Anhydride
21Friedel-Crafts Acylation of Ferrocene
22Grignard Formation of Crystal Violet
23Synthesis of Fluorescein
24Synthesis of Methyl Orange and Its Application to Textiles
25Analysis of Natural Products
26Using a Gas Chromatograph: Identifying an Unknown Compound

Experiment 20 from Organic Chemistry with Vernier Lab Book

<i>Organic Chemistry with Vernier</i> book cover

Included in the Lab Book

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