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Chapter 16: PROBLEM 16.72 (page 640)

Question: Devise a synthesis of X from the given starting materials. You may use any organic or inorganic reagents. Account for the stereochemistry observed in X.

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01

Diels-Alder reaction

The Diels-Alder reaction occurs when a diene (conjugated diene) reacts with an alkene. The reaction may form exo or endo products.

The endo product is formed towards the cavity and the exo is formed above the cavity.

02

Stereochemistry of Diels-Alder reaction

The stereochemistry of the Diels-Alder product is determined by the orientation of groups. For example, the outside groups have cis stereochemistry.

03

Explanation

The given product is formed by the Diels-Alder reaction followed by the ozonolysis reaction in the presence of reducing agents.

Here, both methyl groups are on the same side. Therefore, it is a cis product. The stereochemistry of hydrogen in the endo product is above the plane as the reaction is towards the cavity.

The reaction scheme is shown below:

Diels-Alder reaction

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Most popular questions from this chapter

Question: Draw additional resonance structures for each ion.

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d.

Question: Zingiberene and 尾-sesquiphellandrene, natural products obtained from ginger root, contain conjugated diene units. Which diene reacts faster in the Diels鈥揂lder reaction and why?

Question: Draw the products of the following Diels鈥揂lder reactions. Indicate stereochemistry where appropriate.

a.

b.

c.

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Question: What diene and dienophile are needed to prepare each product?

a.

b.

c.

Question:(a) Which triene has the largest heat of hydrogenation?(b) Which triene has the smallest heat of hydrogenation?(c) Which triene absorbs the longest wavelength of UV light?(d) Which triene is most reactive in the Diels-Alder reaction?
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