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Chapter 17: Q28P (page 883)

What substituted alkene would you use in the Heck reaction to make the following products?

Short Answer

Expert verified

猞� The substituted alkene used in the first reaction is

猞� The substituted alkene used in the second reaction is

Step by step solution

01

Heck Reaction

Heck reaction is the palladium-catalyzed cross-coupling of alkene to arene or other alkenes. This reaction follows a catalytic cycle mechanism around the role of palladium.

Heck reaction has a relatively high functional group tolerance, which means the other sidereaction doesn't happen with a palladium catalyst.

02

Subpart (a) Alkene used to get the desired product:

In the product, the methyl acrylate alkene is coupled with the reactant in presence of a palladium catalyst to get the desired product.

Here, methyl acrylate forms the desired product.

03

Subpart (b) Alkene is used get the desired product:

The acrylonitrile alkene is coupled with the reactant in presence of a palladium catalyst to get the desired product.

Here, Acrylonitrile alkene forms the desired product.

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Most popular questions from this chapter

When anthracene is added to the reaction of chlorobenzene with concentrated NaOH at 350 掳C, an interesting Diels鈥揂lder adduct of the formula C20H14results. The proton NMR spectrum of the product shows a singlet of area 2 around d 3 and a broad singlet of area 12 around d 7. Propose a structure for the product, and explain why one of the aromatic rings of anthracene reacted as a diene.

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)

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

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

(a) buta-1,3-diene

(b) cyclopenta-1,3-diene

Unlike most other electrophilic aromatic substitutions, sulfonation is often reversible. When one sample of toluene is sulfonated at 0 掳C and another sample is sulfonated at 100 掳C, the following ratios of substitution products result:

(a) Explain the change in the product ratios when the temperature is increased.

(b) Predict what will happen when the product mixture from the reaction at 0 掳C is heated to 100 掳C.

(c) Because the SO3Hgroup can be added to a benzene ring and removed later, it is sometimes called a blocking group. Show how 2,6-dibromotoluene can be made from toluene using sulfonation and desulfonation as intermediate steps in the synthesis
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