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Chapter 17: Q26P (page 881)

What organocuprate reagent would you use for the following substitutions?

Short Answer

Expert verified
  1. The organocuparate reagent used for the first reaction is


b. The organocuparate reagent used for the second reaction is



Step by step solution

01

Organocuprate Reagent.

Organocuprate reagent (RCuLi) is synthesized from organolithium reagent (RLi).

Organocuprate reagents are very useful for converting alkyl halide into alkanes, e.g.

1-bromobutane with organocuprate reagent (CH3)2 CuLi bromine is replaced by the methyl group and thus forms pentane, shown below:

02

Subpart (a) The reagent used for the given reaction.

In the product, four-carbon chain butane is coupled to the given reactant iodobenzene.

Here, the organocuprate reagent used isCH3CH2CH2|CH32CuLi

Alkyl cuprate reagent

03

Subpart (b) The reagent used for the given reaction.

In the product, ethene is coupled to the given reactant 3-Bromo-2-butanone.

Here, the organocuprate reagent used is (CH2=CH2)2CuLi .

Lithium divinylcuprate reagent

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