Ch. 17 - Reactions of Aromatic Compounds

Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook

Wade 9th Edition

Ch. 17 - Reactions of Aromatic Compounds

Problem 29a

Chapter 17, Problem 29a

What products would you expect from the following Suzuki coupling reactions?
(a)

Verified step by step guidance

Step 1: Recognize that this is a Suzuki coupling reaction, which involves the cross-coupling of an aryl halide (in this case, a bromobenzene derivative) with an organoboron compound (in this case, a phenylboronic acid derivative) in the presence of a palladium catalyst and a base.

Step 2: Identify the two reactants. The aryl halide is 4-bromo-1-isopropylbenzene, and the organoboron compound is 4-methylphenylboronic acid. The palladium catalyst (Pd(OAc)₂) and base (K₃PO₄) facilitate the reaction.

Step 3: Understand the mechanism. The palladium catalyst first undergoes oxidative addition with the aryl halide, forming a palladium complex. The organoboron compound then reacts with the palladium complex via transmetalation, transferring the aryl group from boron to palladium.

Step 4: The final step is reductive elimination, where the two aryl groups (one from the aryl halide and one from the organoboron compound) couple together, forming a new carbon-carbon bond. This results in the formation of a biaryl product.

Step 5: Combine the two aryl groups. The product of this reaction will be 4-isopropyl-1-(4-methylphenyl)benzene, where the isopropyl group and methyl group remain intact on their respective benzene rings.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.

Video duration:

Was this helpful?

Key Concepts

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

Suzuki Coupling Reaction

The Suzuki coupling reaction is a widely used method in organic chemistry for forming carbon-carbon bonds. It involves the reaction of an organoboron compound with a halogenated organic compound in the presence of a palladium catalyst and a base. This reaction is particularly valuable for synthesizing biaryl compounds, which are important in pharmaceuticals and materials science.

Palladium Catalysis

Palladium catalysis is crucial in many cross-coupling reactions, including the Suzuki reaction. Palladium serves as a catalyst that facilitates the oxidative addition of the halide to the palladium center, followed by transmetalation with the organoboron compound. The use of palladium allows for milder reaction conditions and higher selectivity in forming desired products.

Transmetalation

Transmetalation is a key step in the Suzuki coupling mechanism where the organoboron compound transfers its organic group to the palladium complex. This step is essential for forming the new carbon-carbon bond. The efficiency of transmetalation can be influenced by the choice of base and the nature of the organoboron compound, impacting the overall yield of the reaction.

Recommended video:

Guided course

05:13

Buchwald-Hartwig Amination Reaction

Related Practice

Textbook Question

What products would you expect from the following reactions?

(a)

972

views

Textbook Question

Show how you would use Suzuki reactions to synthesize these products from the indicated starting materials. You may use any additional reagents you need.

(b)

624

views

Textbook Question

Show how you would use Suzuki reactions to synthesize these products from the indicated starting materials. You may use any additional reagents you need.

(a)

1002

views

Textbook Question

What substituted alkene would you use in the Heck reaction to make the following products?

(a)

(b)

1499

views

Textbook Question

What products would you expect from the following Suzuki coupling reactions?

(b)