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The highly reactive triple bond of benzyne is a powerful dienophile. Predict the product of the Diels–Alder reaction of benzyne (from chlorobenzene and NaOH, heated) with cyclopentadiene.

Short Answer

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The predicted product is

Step by step solution

01

Diels – Alder Reaction

Diels- Alder reaction is similar to Michael reactionas both are 1,4 – addition reaction in this cyclic reaction product is formed thus also known as cyclic addition or cycloaddition reaction.

The product formed in Diels – Alder reaction is called adduct, here the reaction takes place between a conjugated diene and alkene or substituted alkene.

02

Product formed in Diels – Alder Reaction

In Diels Alder's reaction, two molecules combine to form a new ring in a one-step, known as a concerted reaction. This reaction involves the concerted forming and breaking of bonds within a closed ring of interacting orbitals.

Benzyne (produced from chlorobenzene and NaOH, heated) act as the dienophile when reacted with cyclopentadiene acting as a diene Diels alder reaction occurs and forms the new ring as the final product in Diels Alder's reaction.

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Most popular questions from this chapter

What products would you expect from the following reactions?

Phenolphthalein, a common nonprescription laxative, is also an acid-base indicator that is colorless in acid and red in base. Phenolphthalein is synthesized by the acid-catalyzed reaction of phthalic anhydride with 2 equivalents of phenol.

(a) Propose a mechanism for the synthesis of phenolphthalein.

(b) Propose a mechanism for the conversion of phenolphthalein to its red dianion in the base.

(c) Use resonance structures to show that the two phenolic oxygen atoms are equivalent (each with half a negative charge) in the red phenolphthalein dianion.


Phthalic anhydride Phenolphthalein red dianion

Which reactions will produce the desired product in good yield? You may assume that aluminum chloride is added as a catalyst in each case. For the reactions that will not give a good yield of the desired product, predict the major products.

Reagents Desired Product

(a) benzene + n-butyl bromide n-butylbenzene

(b) ethylbenzene + tert-butyl chloride p-ethyl-tert-butylbenzene

(c) bromobenzene + ethyl chloride p-bromoethylbenzene

(d) benzamide (PhCONH3) + CH3 CH2 CI p-ethylbenzamide

(e) toluene + HNO3, H2SO4 , heat 2,4,6-trinitrotoluene (TNT)

Propose mechanisms for the Birch reductions of benzoic acid and anisole just shown. Show why the observed orientation of reduction is favored in each case.

A common illicit synthesis of methamphetamine involves an interesting variation of the Birch reduction. A solution of ephedrine in alcohol is added to liquid ammonia, followed by several pieces of lithium metal. The Birch reduction usually reduces the aromatic ring, but in this case, it eliminates the hydroxy group of ephedrine to give methamphetamine. Propose a mechanism, similar to that for the Birch reduction, to explain this unusual course of the reaction

Ephedrine Methamphetamine

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