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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

Draw the products formed in each reaction.

a.

b.

c.

d.

e.

f.

g.

h.

What starting material is needed to synthesize each compound by a ring-closing metathesis reaction?

a.

b.

c.

Draw the coupling product formed when each pair of compounds is treated with Pd(OAc)2, P(o-tolyl)3, and Et3N.

What ring-closing metathesis product is formed when each substrate is treated with Grubbs catalyst under high-dilution conditions?

a.

b.

c.

The reaction of cyclohexene with iodo-benzene under Heck conditions forms E, a coupling product with the new phenyl group on the allylic carbon, but none of the “expected” coupling product F with the phenyl group bonded directly to the carbon–carbon double bond.

a. Draw a stepwise mechanism that illustrates how E is formed.

b. Step [2] in Mechanism 26.2 proceeds with syn addition of Pd and R' to the double bond.What does the formation of E suggest about the stereochemistry of the elimination reaction depicted in Step [3] of Mechanism 26.2?
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