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Chapter 26: Q 43. (page 1073)

Devise a synthesis of each compound using a Heck reaction as one step. You may use benzene, CH2=CHCO2Et, organic alcohols having two carbons or fewer and any required inorganic reagents.

a.

b.

Short Answer

Expert verified

Answer

a.

b.

Step by step solution

01

Heck reaction

The reaction between an unsaturated alkyl halide and an alkene in the presence of a palladium catalyst and a base yielding a substituted alkene is named the Heck reaction.

02

Example of a Heck reaction

Example of a Heck reaction

03

Synthesis of compound a

The reaction involves three steps:

  • Synthesis of p-bromoanisole


Synthesis of p-bromoanisole

  • Synthesis of p-bromoanisole

Synthesis of the aromatic alkene

  • Heck reaction


Heck reaction yielding compound a

04

Synthesis of compound b

The reaction involves the following steps:

  • Synthesis of 4-Bromo-2-ethylanisole


Synthesis of 4-Bromo-2-ethylanisole

  • Heck reaction

Heck reaction yielding compound b

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Most popular questions from this chapter

Sulfur ylides, like the phosphorus ylides of Chapter 21, are useful intermediates in organic synthesis. Methyl trans-chrysanthemate, an intermediate in the synthesis of the insecticide pyrethrin I (Section 26.4), can be prepared from diene A and a sulfur ylide. Draw a stepwise mechanism for this reaction.

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