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Chapter 16: PROBLEM 16.23 (page 625)

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

a.

b.

c.

Question: Farnesyl diphosphate is synthesized from isopentenyl diphosphate and X by a pathway similar toMechanism 16.1. Draw the structure of X.

Question: Why is the bond dissociation energy for the C-C bond in ethane much higher than the bond dissociation energy for the labeled C-C in but-1-ene?

Question: Intramolecular Diels鈥揂lder 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 Diels鈥揂lder reaction.

a.

b.

Question: Devise a stepwise synthesis of each compound from dicyclopentadiene using a Diels鈥揂lder reaction as one step. You may also use organic compounds having 鈮� 4 C鈥檚, and any required organic or inorganic reagents:

a.

b.

c.
See all solutions

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