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Chapter 26: Q 3. (page 1052)

Synthesize each product from the given starting materials using an organocuprate coupling reaction.

Short Answer

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Answer

a.

b.

c.

Step by step solution

01

Organocuprate coupling reaction

An organic reaction involves the formation of a new carbon-carbon bond by coupling two moles of an alkyl halide with an organocuprate reagent(R2CuLi) .

02

Synthesising compounds

The given compounds are synthesized as follows:

a. The bromobenzene is treated with lithium and cupric iodide to form the corresponding lithium diphenyl cuprate. This is allowed to react with organo iodide to form the required

compound.

Organocuprate coupling reaction to form substituted benzene

b.Butyl chloride reacts with lithium, followed by cupric iodide to form the lithium dibutyl cuprate that reacts with bromobutene to form the required hydrocarbon.

Organocuprate synthesis of Oct-3-ene.

c. 1-Chloro-3-methyl propane reacts with lithium, followed by cupric iodide to form lithium 3-methyl propane cuprate that reacts with another molecule of 1-chloro-3-methyl propane to form the required hydrocarbon.


Organocuprate synthesis of 3,8-dimethyldecane.

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Most popular questions from this chapter

Devise a synthesis of each substituted cyclopropane. Use acetylene HC鈮�CH, as a startingmaterial in part (a), and cyclohexanone as a starting material in part (b). You may use anyother organic compounds and any needed reagents.

a.

b.

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

a.

b.

c.

Draw a stepwise mechanism for the following reaction.

Draw the products formed when each alkene is treated with Grubbs catalyst.

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.
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