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Chapter 26: Q 24. (page 1069)

What steps are needed to convert but-1-ene CH3CH2CH=CH2 to octane role="math" localid="1649049664153" [CH3CH26CH3]using a coupling reaction with an organocuprate reagent? All carbon atoms in octane must come from but-1-ene.

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01

Coupling reactions

Coupling reactions can be of several types, and one among them is the organocuprate coupling reaction. These reactions are stereospecific if the organic halide is a vinyl halide.

02

Features of organocuprate coupling reactions

The product generated by combining an organic halide with an organocuprate reagent comprises a new C-C bond. Several organic halides, such as methyl alkyl halide and vinyl halides, can be employed for this reaction.

03

Conversion of but-1-ene to octane using a coupling reaction

But-1-ene undergoes reaction with HBr and peroxide to form 1-bromobutane. The resultant product can react with Li and CuI to form the organocuprate reagent. This reagent can couple with but-1-ene to form octane. The reaction can be given as follows.

Conversion of but-1-ene to octane

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Most popular questions from this chapter

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

What product is formed by ring-closing metathesis of compound V, a key intermediate in the synthesis of ingenol, a natural product mentioned in the chapter opener?

Draw the structure of the two products of molecular formulaC15H26O2 formed when M is treated with Grubbs catalyst under high-dilution conditions.

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.

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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