Question
Norbornadiene (Problem 14.46 ) can be prepared by reaction of chloroethylene with 1,3 -cyclopentadiene, followed by treatment of the product with sodium ethoxide. Write the overall scheme, and identify the two kinds of reactions.
Step 1
This is a Diels-Alder reaction, which is a type of cycloaddition reaction. In this reaction, a diene (a molecule with two alternating double bonds) reacts with a dienophile (a molecule with a double or triple bond) to form a cyclic compound. The reaction can be Show more…
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a. Write a mechanism and final product for the reaction between sodium ethoxide, $\mathrm{NaOCH}_{2} \mathrm{CH}_{3}$, and bromoethane, $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Br}$, in ethanol solvent, $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}$.
lntramolecular Diels-Alder reactions are possible when a substrate contains both a 1,3-diene and a dienophile, as shown in the following general reaction. With this in mind, draw the product of each intramolecular Dials-Alder reaction.
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