CHM 207 Experiment 11

does the two carboxylic acids effect the location of where the C=O peaks are?

YES, one will be ~ 1790 and the other ~1693

why is the temperature controlled around 60-70?

because the diene is very volatile

what is so important about diol-alder reactions?

they build rings very efficiently and easily and is stereospecific

what does the IR look like?

two C=O bond seen

If the hydrolysis to the diacid is not complete, how could you separate the desired diacid from the unhydrolyzed anhydride by extraction?

If the hydrolysis of the diacid was not completed the diacid could be separated by adding a base and an acid. First, the base would need to be strong in order to make the desired acid soluble in water and create an aqueous layer to remove. After this is done, the acid would need to be added to help separate the desired diacid from the unhydrolyzed anhydride.

Which side reaction could occur in this experiment if the toluene were not completely dry? Show reaction.

If the toluene was not completely dry in the reaction, the side reaction that would occur would involve maleic anhydride turning into maleic acid.

In the Diels-Alder reactions shows in Equation 8-1, the number of sigma bonds and the pi bonds have:

Increased by two and decreased by two, respectively

Experiment 11

The Diels Alder reaction

Draw the exo and endo product for the reaction of cyclopentadiene and maleic anhydride. Which one will be favored?

The endo product will be favored for this reaction because it is the more stable product.