Predict the products of the following Diels-Alder reactions.

a)

b)

c)

d)

Short Answer

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a)

b)

c)

d)

Step by step solution

01

Diels-Alder reaction

The Diels Alder reaction comprises a concerted mechanism where the bond making and breaking happens in a single step. These reactions are identical to a nucleophile-electrophile reaction.

02

Stereochemistry of the Diels-Alder reaction

The different stereochemical features of the Diels-Alder reactions include s-cis conformation of the Diene, syn stereochemistry and the endo rule.A secondary overlap among the p orbitals of the electron-withdrawing group and the central carbon atoms of the diene happens in a Diels-Alder reaction.

03

Predicting the products of the Diels-Alder reaction

(a)

The treatment of 2-methoxycyclopenta-1,3-diene with methyl propionate forms a new carbon-carbon bond in the resulting product. The reaction can be given as:

Diels-Alder reaction of compound a

(b)

The treatment of 1-methoxycyclohexa-1,3-diene with cyclohex-2-enone creates the product. The reaction can be given as:

Diels-Alder reaction of compound b

(c)

The treatment of 2-methoxybuta-1,3-diene with acylaldehyde creates the product. The reaction can be given as:

Diels-Alder reaction of compound c

(d)

The treatment of (E)-2-methylpenta-1,3-diene with acrylonitrile generates the product. The reaction can be given as:

Diels-Alder reaction of compound d

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Most popular questions from this chapter

Question: When N-bromosuccinimide is added to hex-1-ene in CCl4and a sunlamp is shone on the mixture, three products result.

  1. Give the structures of these three products.
  2. Propose a mechanism that accounts for the formation of these three products.

(a)Show that the [4+4] cycloaddition of two butadiene molecules to give cycloocta-1,5-diene is thermally forbidden but photochemically allowed.

(b)There is a different, thermally allowed cycloaddition of two butadiene molecules. Show this reaction, and explain why it is thermally allowed. (Hint: Consider the dimerization of cyclopentadiene.)

In Solved Problem 15-2, we simply predicted that the products would have a 1, 2-or 1, 4-relationship of the proper substitutents. Draw the charge-separated resonance forms of the reactants to support these predictions.

Question: When Br2 is added to buta-1,3- diene at -150C , the product mixture contains 60% of product A and 40% of product B. When the same reaction takes place at 600C , the product ratio is 10% A and 90% B.

a. Propose structures for products A and B (Hint: In many case, an allylic carbocation is more stable than a bromonium ion.)

b. Propose a mechanism to account for formation of both A and B.

c. Show why A predominates at -150C and B predominates at 600C .

d. If you had a solution of pure A, and its temperature were raised to600C , what would you expect to happen ? Propose a mechanism to support your prediction.

When methylenecyclohexane is treated with a low concentration of bromine under irradiation by a sunlamp, two substitution products are formed.

  1. Propose structures for these two products.
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