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Exp. 1 Report / Diels Alder
1) Draw the product of your synthesis clearly indicating the stereochemistry (cis, trans) about the cyclohexane
ring for each substituent. Note that all four cyclohexane substituents are cis.
2) Provide mechanisms for each reaction in the synthesis and discuss the reactivity of the diene and the
dienophile. (Hint: Consult your text for the impact of electron withdrawing and electron donating groups on
Diels Alder reactions).
3) Report the yield for the synthesis in both grams and percent and show your calculations.
4) Attach, interpret and discuss all data relating to the identification / verification of the product.
5) Predict the product in each of the following Diels-Alder reactions.
a.
MeO 2C
CO 2Me
b.
+
O
+
O
O
c.
+
CN
6) Cyclopentadiene reacts as a diene in the Diels-Alder reaction a great deal more readily than does 1,3butadiene. Explain.
7) Predict the reactant diene and dienophile that would lead to each of the following products.
a.
b.
O
CH3
c.
O
CO 2Et
CO 2Et
Me
Me
8) Two regioisomers are formed when 2-methyl-1,3-butadiene reacts with ethyl acrylate. Draw structures for
these isomers and the mechanism for the formation of each.
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