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Chapter 26: Q 6. (page 1056)

Synthesize each compound from the given starting materials.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Suzuki reaction

The reaction involving the palladium-metal catalyzed coupling of an alkyl or vinyl halide with an organoborane in the presence of a base to form a product with a new C-C bond is known as the ‘Suzuki reaction.’ It is a highly stereospecific reaction.

The given compounds are synthesized by Suzuki reaction as follows:

02

Synthesising compounds

a. Butyne reacts with an organoborane, followed by vinyl iodide to form the given compound.

Formation of 4,6-decadiene

b. Iodobenzene reacts with an organoborane, followed by another molecule of iodobenzene in the presence of a palladium catalyst in a basic medium to form the required diphenyl.

Formation of diphenyl

c. Acetophenone would undergo bromination, followed by lithiation to react with an organoborane. The compound would further react with a vinyl halide in the presence of a palladium catalyst in a basic medium to form the required compound.


Formation of compound c.

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Most popular questions from this chapter

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.

Devise a synthesis of each compound from benzene. You may also use any organic compounds having four carbons or fewer, and any required inorganic reagents.

a.

b.

What reagents are needed to carry out transformations [1]–[3] in the synthesis of aldehyde A? A can be converted to the antitumor agent maytansine in several steps.

What starting materials are needed to prepare each compound using a Heck reaction?

What product is formed by ring-closing metathesis of each compound?

a.

b.
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