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Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
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All textbooksMullins 1st EditionCh. 23 - Benzene I: Aromatic Stability and Substitution ReactionsProblem 60a
Chapter 22, Problem 60a

Suggest two coupling partners that could be used to synthesize the compounds shown making the indicated C―C bonds.
(a)

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1
Identify the C―C bond that needs to be formed in the target molecule. This will help in determining the two fragments or coupling partners required for the synthesis.
Consider the use of a common coupling reaction, such as the Suzuki-Miyaura coupling, which involves the reaction between an organoboron compound and an organohalide in the presence of a palladium catalyst.
Determine the retrosynthetic disconnection at the C―C bond. This involves breaking the target molecule into two simpler fragments that can be used as starting materials.
Select the appropriate organoboron compound and organohalide that, when coupled, will form the desired C―C bond. For example, if the target bond is between a phenyl group and an alkyl chain, you might choose a phenylboronic acid and an alkyl halide.
Ensure that the chosen coupling partners are compatible with the reaction conditions and that they will not interfere with other functional groups present in the molecule.

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Key Concepts

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

Cross-Coupling Reactions

Cross-coupling reactions are a class of reactions in organic chemistry where two different organic groups are joined together through the formation of a carbon-carbon bond. Common examples include the Suzuki, Heck, and Stille reactions, which utilize metal catalysts to facilitate the coupling of organometallic reagents with electrophiles. Understanding these reactions is crucial for identifying suitable coupling partners in synthetic pathways.
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Organometallic Reagents

Organometallic reagents are compounds that contain a carbon-metal bond, where the carbon is typically bonded to a metal such as lithium, magnesium, or palladium. These reagents are essential in cross-coupling reactions as they provide the nucleophilic carbon species that can react with electrophiles to form new C―C bonds. Familiarity with the properties and reactivity of various organometallics is vital for selecting appropriate coupling partners.
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Electrophiles in Organic Synthesis

Electrophiles are electron-deficient species that can accept electron pairs from nucleophiles during chemical reactions. In the context of cross-coupling, electrophiles often include halides or other leaving groups that can react with organometallic reagents. Recognizing the nature of potential electrophiles is essential for determining effective coupling partners and predicting the outcome of synthetic reactions.
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Related Practice
Textbook Question

Predict the products of the following reactions.

(a)

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Textbook Question

(i) Classify the following molecules as aromatic, nonaromatic, or antiaromatic.

(ii) For aromatic molecules, solve for n in Hückel’s rule. For all other molecules, explain which rule of aromaticity is being broken.

(a)

845
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Textbook Question

Conversion of t-butylbenzene to a phenol results in two products when the reaction occurs through the benzyne mechanism. Devise a sequence involving a diazonium ion in which only one phenol product is produced.

455
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Textbook Question

Predict the products of the following reactions.

(b)

595
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Textbook Question

(i) Classify the following molecules as aromatic, nonaromatic, or antiaromatic.

(ii) For aromatic molecules, solve for n in Hückel’s rule. For all other molecules, explain which rule of aromaticity is being broken.

(c)

339
views
Textbook Question

(i) Classify the following molecules as aromatic, nonaromatic, or antiaromatic.

(ii) For aromatic molecules, solve for n in Hückel’s rule. For all other molecules, explain which rule of aromaticity is being broken.

(b)

540
views