The Diels-Alder Reaction & Acetylation of Aniline

Aldol Condensation Reaction

* Finish this experiment by taking final masses and melting points of the crude and recrystallized 3-nitrochalcone.

Synthesis of β-Benzopinacolone

* Take a 25mL RB flask and add 5mL of 0.015 M solution of iodine that’s dissolved in glacial acetic acid.

* Add 1g of benzpinacol. Then attach the RB flask to a water-cooled condenser. Use a heating mantel as the heat source, and then perform a reflux for 5 mins. There might be crystals that appear while the solution is heating.

* Take away the heating mantel and let the solution cool. The product will crystallize as it cools.

* When the product is cooled till room temp, gather the crystals by vacuum filtration using a small Buchner funnel.

* Wash the crystals with three 2mL portions of cold acetic acid.

* Let the crystals dry overnight. Mass and determine the melting pt.(Pure β-Benzopinacolone melts at 182°C), Also do an IR using dry film(one plate), and an NMR in carbon tetrachloride.

* Calculate percent yield, turn in product to instructor, in a vial. Also turn in the spectra, identify how they prove that the product undergoes rearrangement.

Synthesis of Acetanilide

* Measure and mass 1.4-mL aniline in a 10-mL graduated cylinder and add to 50-mL RBF.

* While in the hood, add 1.4-mL acetic anhydride to RBF measured in the unwashd 10-mL graduated cylinder to help transfer all the aniline.

* Take a small heating mantle & cooling condenser to reflux for 30 minutes.  (Don’t clean cooling condenser from previous reflux.)  During reflux perform Diels-Alder Reaction.

* Transfer the hot solution into 100-mLs cold DI water in a 250-mL beaker.

* Let it cool on ice for 10 minutes.

* Vacuum filter using NaOH traps, and then rinse with cold water. 

* Let the product dry on labeled watch glass until next week.  This is next week’s starting material.

The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride

Prep of the...