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Ch. 21 - Conjugated Systems I: Stability and Addition Reactions
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
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All textbooksMullins 1st EditionCh. 21 - Conjugated Systems I: Stability and Addition ReactionsProblem 47
Chapter 20, Problem 47

To this point, we have seen four reactions that can be done by Gilman reagents. What are they? What do they have in common?

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Gilman reagents, also known as organocuprates, are typically used in organic synthesis for nucleophilic substitution reactions. They are formed by reacting organolithium compounds with copper(I) iodide.
The first reaction involving Gilman reagents is the coupling reaction with alkyl halides. This reaction allows the formation of new carbon-carbon bonds by replacing the halide group with the alkyl group from the Gilman reagent.
The second reaction is the conjugate addition to α,β-unsaturated carbonyl compounds. Gilman reagents add to the β-position of the unsaturated system, forming a new carbon-carbon bond.
The third reaction is the opening of epoxides. Gilman reagents can attack the less hindered carbon of an epoxide, leading to ring opening and formation of an alcohol.
The fourth reaction is the substitution of acyl chlorides to form ketones. Gilman reagents replace the chloride in acyl chlorides, resulting in the formation of ketones. All these reactions involve the formation of new carbon-carbon bonds, showcasing the nucleophilic nature of Gilman reagents.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Gilman Reagents

Gilman reagents, also known as organocopper compounds, are used in organic synthesis for forming carbon-carbon bonds. They are typically composed of lithium diorganocuprates, which are versatile in reactions such as conjugate additions and coupling with halides. Understanding their structure and reactivity is crucial for predicting their behavior in various reactions.
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Conjugate Addition

Conjugate addition involves the addition of a nucleophile to the beta position of an alpha, beta-unsaturated carbonyl compound. Gilman reagents are particularly effective in this type of reaction, allowing for the formation of new carbon-carbon bonds while avoiding direct addition to the carbonyl group. This reaction is essential for synthesizing complex organic molecules.
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Cross-Coupling Reactions

Cross-coupling reactions are a key method for forming carbon-carbon bonds, where Gilman reagents react with organic halides to create new compounds. These reactions are characterized by the transfer of organic groups from the reagent to the halide, facilitated by the copper in the Gilman reagent. Understanding the mechanism and conditions for these reactions is vital for their successful application in synthesis.
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Related Practice
Textbook Question

Would you expect the following molecules to absorb in the UV–visible region of the electromagnetic spectrum?

(a)

(b)

(c)

(d)

(e)

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Textbook Question

Suggest a reagent and a reactant that could be used to form the following molecules by conjugate addition of a cuprate. There can be multiple possibilities.

(a)

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Textbook Question

Suggest a reagent and a reactant that could be used to form the following molecules by conjugate addition of a cuprate. There can be multiple possibilities.

(c)

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Textbook Question

Suggest a reagent and a reactant that could be used to form the following molecules by conjugate addition of a cuprate. There can be multiple possibilities.

(b)

1
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Textbook Question

On a per alkene basis, which would have the more negative heat of hydrogenation?

1
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Textbook Question

How many 𝝅 electrons are involved in the conjugated system for each of the following molecules?

(a)

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