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Chapter 16: PROBLEM 16.24 (page 627)

Question: Draw the product of each Diels–Alder reaction.

a.

b.

Short Answer

Expert verified

Answer

a.

b.

Step by step solution

01

Diels-Alder reaction

Diels-Alder reaction is also known as 4π+2π cycloaddition.

This reaction is thermally allowed, but it is photochemically forbidden.

02

Mechanism of Diels-Alder reaction

Mechanism of the Diels-Alder reaction using an example is shown below:

Mechanism of Diels-Alder reaction

03

To find the product of the reaction

The product with endo substitution will be preferred for the Diels-Alder reaction.

The Diels-Alder reaction of cyclopentadiene is shown below:

Diels-Alder reaction

The product obtained contains an endo substituent.

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Most popular questions from this chapter

Question. Draw all possible resonance structures for the following cation and indicate which structure makes the largest contribution to the resonance hybrid.

Question: Name each diene and state whether the ball-and-stick model shows the diene in the s-cis or s-trans conformation.

a.

b.

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?

Question: Draw a stepwise mechanism for the following reaction.

Question: Devise a stepwise synthesis of each compound from dicyclopentadiene using a Diels–Alder reaction as one step. You may also use organic compounds having ≤ 4 C’s, and any required organic or inorganic reagents:

a.

b.

c.
See all solutions

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