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Chapter 17: Q27P (page 882)

What products would you expect from the following reactions?

Short Answer

Expert verified

In heck reaction,alkyl halide, aryl halide, or pseudo alkyl halide react with electron-deficient species and palladium zero catalysts to give the cross-coupled product.

This reaction is stereoselective, so trans alkene is obtained rather than cis alkene due to steric hindrance during the coupling reaction.

Step by step solution

01

Heck Reaction

In heck reaction,alkyl halide, aryl halide, or pseudo alkyl halide react with electron-deficient species and palladium zero catalysts to give the cross-coupled product.

This reaction is stereoselective, so trans alkene is obtained rather than cis alkene due to steric hindrance during the coupling reaction.

02

Subpart (a) Excepted product from the given reactant.

Aryl halide 1-(4-bromophenyl)ethanone with an alkene 4-methoxypent-1-ene in the presence of palladium catalyst gives a new C-C bond at the less substituted end of the alkene, usually with trans stereochemistry.

Trans alkene product

03

Subpart (b) Excepted product from the given reactant.

Alkyl halide (Z)-2-bromopent-2-ene with an alkene 1-methoxy-4vinylbenzene in the presence of palladium catalyst gives a new C-C bond at the less substituted end of the alkene, usually with trans stereochemistry.

Trans alkene product

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Most popular questions from this chapter

Propose a mechanism for the reaction of benzyl bromide with ethanol to give benzyl ethyl ether (shown above).

Triphenylmethanol is insoluble in water, but when it is treated with concentrated sulfuric acid, a bright yellow solution results. As this yellow solution is diluted with water, its color disappears and a precipitate of triphenylmethanol reappears. Suggest a structure for the bright yellow species, and explain this unusual behavior.

Show how you would synthesize the following compounds, using the indicated starting materials.

(a) 3-phenylbutan-1-ol from styrene

Propose a mechanism for the aluminum chloride-catalyzed reaction of benzene with chlorine.

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 C6H2OBr4 precipitates 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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