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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

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

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

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.

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

Step 2 of the iodination of benzene shows water acting as a base and removing a proton from the sigma complex. We did not consider the possibility of water acting as a nucleophile and attacking the carbocation, as in an electrophilic addition to an alkene. Draw the reaction that would occur if water reacted as a nucleophile and added to the carbocation. Explain why this type of addition is rarely observed.
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