[jlko0221]

I have hw from my Organic chem lab dealing with a Diels-Alder reaction we synthesized in class and was wondering if anyone could help me. It's only a couple of questions, im going to the chem lab to review them as well. I'm giving a recap of the lab cause i can't find pictures to describe the reaction.

In the lab, we started with 180-220mg maleic anhydride, then added 1mL of toluene followed by an equimolar amount of 2,3-dimethyl-1,3 butadiene (Under euimolar conditions). We heated for 30 min and added 2mL of hexanes. Then cooled and dried the product and added 10mL of water and 3 drops of HCL as a catalyst. Heated till dissolved and then cooled and dried it.

so here are the questions:

1.which side reaction could occur in this experiment if the toluene were not completely dry? Show reaction (I dont know if anyone could show the reaction on a comp)

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

3. Assuming we start with 200mg of cyclopentadiene and 300mg of maleic anhydride, and 375mg of the cycloadduct anhydride is obtained:

a. which is the limiting reagent?

b. calculate percent yeild for the anhydride

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

5. Complete the following reactions. Indicate stereochemistry when appropriate: its the 4 figures of the attached picture

[nj_bartel]

You need to show your attempts.

[jlko0221]

what do you mean show attempts?

[nj_bartel]

at solving your questions

[orgopete]

You also have questions with different kinds of answers. That makes it difficult to understand what you don't understand. What did you get for the yield?

Here is an example of a reaction that gives an endo product as the major isomer. You could also use it as a model for your other Diels-Alder reactions. You should use similar curved arrows to draw the other reaction products even if they do not have an endo stereochemical descriptor. That is, maintain all other bond stereochemistry, trans to trans, etc.


_{This example is excerpted from A Handbook of Organic Chemistry Mechanisms©.}