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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

What organocuprate reagent would you use for the following substitutions?

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)

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(a) isopropylbenzene

(b) p-xylene

(c) tetralin

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Phenol reacts with three equivalents of bromine in CCl4 (in the dark) to give a product of formula C6H3OBr3. When this product is added to bromine water, a yellow solid of molecular formula C6H2OBr4precipitates out of the solution. The IR spectrum of the yellow precipitate shows a strong absorption (much like that of a quinone) around 1680cm-1. Propose structures for the two products.
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