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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

Expert verified

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≡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.

Identify reagents A and B in the following reaction scheme. This synthetic sequence was used to prepare the C18 juvenile hormone (Figure 20.6).

Draw a stepwise mechanism for the following reaction.

What product is formed when each alkene is treated with and Zn(Cu)?

a.

b.

c.

When certain cycloalkenes are used in metathesis reactions, ring-opening metathesis polymerization (ROMP) occurs to form a high molecular weight polymer, as shown with cyclopentene as the starting material. The reaction is driven to completion by relief of strain in the cycloalkene.

What products are formed by ring-opening metathesis polymerization of each alkene?
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