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Chapter 26: Q26P (page 1049)

Identify X, an intermediate that was converted to eletriptan (trade name Relpax), a drug used to treat migraines.

Short Answer

Expert verified

The reaction between an alkene and an alkyl halide group in the presence of a base and a catalyst (palladium) is known as the Heck reaction. In this reaction, an alkene is formed.

Step by step solution

01

Heck reaction

The reaction between an alkene and an alkyl halide group in the presence of a base and a catalyst (palladium) is known as the Heck reaction. In this reaction, an alkene is formed.

02

Mechanism of Heck reaction  

  • In the first step, the divalent palladium catalyst reacts with the alkyl halide (RX) to form an organo-palladium compound.
  • In the second step, the (R) group and palladium (Pd) from the organopalladium compound add to the C=C such that Pd bonds with the more substituted carbon.
  • In the third step, the elimination of hydrogen and palladium takes place. Then, by reductive elimination, the initial palladium catalyst is regenerated.
03

Products of the given reaction

Compound X is shown here under.

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Most popular questions from this chapter

Draw the product formed from the ring-closing metathesis of each compound. Then, devise a synthesis of each metathesis starting material from benzene, alcohols with less than five carbons, and any needed organic and inorganic reagents.

a.

b.

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

What organic halide is needed to convert lithium divinylcuprate [CH2=CH2CuLi]to each compound?

a.

b.

c.

Dimethyl cyclopropanes can be prepared by the reaction of an α, β-unsaturated carbonyl compound X with two equivalents of a Wittig reagent Y. Draw a stepwise mechanism for this reaction.

Devise a synthesis of each of the following compounds. Besides inorganic reagents, you may use hydrocarbons and halides having ≤C’s, and CH2CHCOOCH3as starting materials. Each synthesis must use at least one of the carbon–carbon bond-forming reactions in this chapter.


b.

c.

d.
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