Skip to main content
Ch. 11 - Organometallic Compounds
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook
Chapter 12, Problem 25a

What compound undergoes metathesis to form each of the following compounds?
a. Chemical structure of a compound relevant to metathesis reactions in organic chemistry.

Verified step by step guidance
1
Step 1: Identify the product formed in the metathesis reaction. The compound shown in the image is a bicyclic structure with a benzene ring fused to a cyclohexene ring. This is 1,2-dihydroacenaphthylene.
Step 2: Understand the metathesis reaction. Metathesis involves the exchange of alkene fragments between molecules, typically catalyzed by a transition metal catalyst such as Grubbs' catalyst.
Step 3: Determine the precursor compound. To form the bicyclic structure shown, the precursor compound must contain two alkenes that can undergo ring-closing metathesis to form the fused ring system.
Step 4: Predict the structure of the precursor. The precursor is likely a compound with two terminal alkenes positioned such that they can form the fused bicyclic structure upon metathesis. For example, a compound with a benzene ring and a cyclohexane ring connected by two terminal alkenes.
Step 5: Verify the reaction mechanism. Ensure that the metathesis reaction proceeds via the formation of a metallacyclobutane intermediate, leading to the desired bicyclic product.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
4m
Was this helpful?

Key Concepts

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

Metathesis Reaction

Metathesis is a chemical reaction in which two compounds exchange parts to form new compounds. In organic chemistry, this often involves the exchange of alkyl groups between alkenes, facilitated by catalysts such as transition metals. This reaction is significant for synthesizing complex molecules and can lead to the formation of valuable products in a more efficient manner.
Recommended video:
2:09
Alkene Metathesis Concept 1

Alkenes

Alkenes are hydrocarbons that contain at least one carbon-carbon double bond. They are unsaturated compounds and are key participants in metathesis reactions. The presence of the double bond allows for the reorganization of carbon skeletons during reactions, making alkenes versatile building blocks in organic synthesis.
Recommended video:
2:09
Alkene Metathesis Concept 1

Catalysts in Organic Reactions

Catalysts are substances that increase the rate of a chemical reaction without being consumed in the process. In metathesis reactions, catalysts such as Grubbs or Schrock catalysts are commonly used to facilitate the exchange of alkyl groups between alkenes. Understanding the role of these catalysts is crucial for optimizing reaction conditions and yields in organic synthesis.
Recommended video:
1:22
Introduction to Catalysis Example 1