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Chapter 17: Q42P (page 845)

1,4-Benzoquinone is a good Diels–Alder dienophile. Predict the products of its reaction with

(a) buta-1,3-diene

(b) cyclopenta-1,3-diene

Short Answer

Expert verified

The acetylenic component that is seeking a diene in the Diels-Alder reaction is known as a dienophile.

Step by step solution

01

Dienophile:

The acetylenic component that is seeking a diene in the Diels-Alder reaction is known as a dienophile.

02

Diels-Alder Reaction:

A chemical reaction in which a conjugated diene and dienophile take part to form a substituted cyclohexene derivative is termed a Diels-alder reaction.

03

Subpart (a) Reaction of 1,4 benzoquinone with buta-1,3-diene.

The product of the reaction is:

04

Subpart (b) Reaction of 1,4 benzoquinone with cyclopenta-1,3-diene.

The product obtained from this reaction is:

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Most popular questions from this chapter

The antioxidants BHA and BHT are commonly used as food preservatives. Show how BHA and BHT can be made from phenol and hydroquinone.

(a) Based on what you know about the relative stabilities of alkyl cations and benzylic cations, predict the product of addition of HBr to 1-phenylpropene.

(b) Propose a mechanism for this reaction.

(c) Based on what you know about the relative stabilities of alkyl radicals and benzylic radicals, predict the product of addition of HBr to 1-phenylpropene in the presence of a free-radical initiator.

(d) Propose a mechanism for this reaction.

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

Starting with benzene and any other reagents you need, show how you would synthesize the compound shown here. (Hint: Consider a Pd-catalyzed coupling for the final step).
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