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Chapter 20: 72P (page 1038)

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

Expert verified

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.

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.

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.

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Most popular questions from this chapter

Explain why the acid-catalyzed condensation is a poor method for the synthesis of an unsymmetrical ether such as ethyl methyl ether, CH3CH2 - O - CH3.

Question: Show how the following ketones might be synthesized from the indicated acids, using any necessary reagents.

(a)propiophenone from propionic acid (two ways, using alkylation of the acid and using Friedel-Crafts acylation)

(b)methyl cyclohexyl ketone from cyclohexanecarboxylic acid

Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.

(a) methyl salicylate

(b) methyl formate (bp 32°C)

(c) ethyl phenylacetate

Question: Arrange each group of compounds in order of increasing basicity.

  1. CH3COO-,CICH2C00- , and PhO-
  2. sodium acetylide, sodium amide, and sodium acetate
  3. sodium benzoate, sodium ethoxide, and sodium phenoxide
  4. pyridine, sodium ethoxide, and sodium acetate

Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solvents you need.
See all solutions

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