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Chapter 16: PROBLEM 16.23 (page 625)

Question: Draw the products of each Diels–Alder reaction, and indicate the stereochemistry.

a.

b.

c.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Diels-Alder reaction

The Diels-Alder reaction occurs between a conjugated diene and an alkene called the dienophile.

The diene in a Diels-Alder reaction will be electron-rich, whereas the diene must be electron-poor alkenes and alkynes.

02

Example of Diels-Alder reaction

An example of Diels-Alder reaction is shown:

Example for Diels-Alder reaction

03

To find the product and stereochemistry

A cis dienophile will always form cis-substituted cyclohexene, and a trans dienophile will always form trans-substituted cyclohexene.

Representation of product of A

Here the dienophile is in cis position, combining with a diene to form a cis-substituted product.

Representation of product of B

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Most popular questions from this chapter

Question: A transannular Diels–Alder reaction is an intramolecular reaction that occurs when the diene and dienophile are contained in one ring, resulting in the formation of a tricyclic ring system. Draw the product formed when the following triene undergoes a transannular Diels–Alder reaction.

Question: For which compounds can a second resonance structure be drawn? Draw an additional resonance structure for each resonance-stabilized compound.

a.

b.

c.

d.

Question: Draw the products formed when each compound is treated with one equivalent of HBr.

a.

b.

c.

Question: Determine the hybridization around the N atom in each amine and explain why cyclohexanamine is 106 times more basic than aniline

Question: Rank the following dienophiles in order of increasing reactivity
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