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Chapter 17: Q72P (page 910)

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).

Short Answer

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Formation of acetophenone

Formation of 3-chloro acetophenone

Formation of the desired product

Step by step solution

01

Formation of 3-chloro acetophenone

In the presence of aluminum chloride, an acyl chloride reacts with benzene to give acetophenone. This reaction is known as Friedel crafts acylation reaction. Keto group is meta director so incoming electrophile attacks meta to keto group. The formed acetophenone undergoes chlorination (electrophilic substitution reaction) to give 3-chloroacetophenone.

Formation of acetophenone

Formation of 3-chloro acetophenone

02

Formation of the desired product

The heck coupling reaction is a palladium-catalyzed cross-coupling reaction in which alkyl halide reacts with an alkene to give the substituted product in a basic medium. The compound,3-chloroacetophenone undergoes a heck coupling reaction with but-1-ene to give the desired product.

Formation of the desired product

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Most popular questions from this chapter

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.

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

Predict the major products of treating the following compounds with hot, concentrated potassium permanganate, followed by acidification with dilute HCl.

(a) isopropylbenzene

(b) p-xylene

(c) tetralin

A graduate student tried to make o-fluorophenylmagnesium bromide by adding magnesium to an ether solution of o-fluorobromobenzene. After obtaining puzzling results with this reaction, she repeated the reaction by using as solvent some tetrahydrofuran that contained a small amount of furan. From this reaction, she isolated a fair yield of the compound that follows. Propose a mechanism for its formation

To synthesize m-ethylbenzenesulfonic acid, a student attempted the Friedel鈥揅rafts alkylation of benzenesulfonic acid with bromoethane. Do you predict that this reaction was successful? If not, propose an alternative synthesis.

m-ethylbenzenesulfonic acid
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