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Chapter 16: 16-4P (page 805)

Show the product of the Diels–Alder dimerization of cyclobutadiene.

Short Answer

Expert verified

It is a reaction in which a cyclohexene derivative is formed by the reaction of dienophile (substituted alkene) and a conjugated diene. This involves the shift of four pi electrons of diene and two pi electrons of dienophile.

Step by step solution

01

Diels-Alder reaction

It is a reaction in which a cyclohexene derivative is formed by the reaction of dienophile (substituted alkene) and a conjugated diene. This involves the shift of four pi electrons of diene and two pi electrons of dienophile.

02

Product of dimerization

Two molecules of cyclobutadiene react to form the Diels-Alder product.

Formation of desired product of Diels-Alder reaction

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Most popular questions from this chapter

(a) Draw the molecular orbitals for the cyclopropenyl case. H H H (Because there are three p orbitals, there must be three MOs: one all-bonding MO and one degenerate pair of MOs.)

(b) Draw an energy diagram for the cyclopropenyl MOs. (The polygon rule is helpful.) Label each MO as bonding, nonbonding, or antibonding, and add the nonbonding line. Notice that it goes through the approximate average of the MOs.

(c) Add electrons to your energy diagram to show the configuration of the cyclopropenyl cation and the cyclopropenyl anion. Which is aromatic and which is antiaromatic?

Explain why each compound is aromatic, antiaromatic, or nonaromatic

(a) Isoxazole

(b) 1,3-thiazole

(c) Pyran

(d) Pyrylium ion

(e) γ - pyrone

(f) 1,2-Dihydropyridine

(g)Cytosine

(h)

(a) Explain how pyrrole is isoelectronic with the cyclopentadienyl anion.

(b) Specifically, what is the difference between the cyclopentadienyl anion and pyrrole?

(c) Draw resonance forms to show the charge distribution on the pyrrole structure


(a) Draw all the Kekulé structures of anthracene and phenanthrene.

(b) Propose mechanisms for the two additions shown.

(c) In Chapter 8, most of the additions of bromine to double bonds gave entirely anti stereochemistry. Explain why the addition to phenanthrene gives a mixture of syn andanti stereochemistry.

(d) When the product from (c) is heated, HBr is evolved, and 9-bromophenanthrene results. Propose a mechanism for this dehydrohalogenation.

The polarization of a carbonyl group can be represented by a pair of resonance structures

Cyclopropenone and cycloheptatrienone are more stable than anticipated. Cyclopentadienone, however, is relatively unstable and rapidly undergoes a Diels–Alder dimerization. Explain.

Cyclopropenone CycloheptatrienoneCyclopentadienone
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