Textbook Question
Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.
(f)
13. Alcohols and Carbonyl Compounds
Organometallic Cumulative Practice
4:08 minutesProblem 25a
Textbook Question
What compound undergoes metathesis to form each of the following compounds?
a. 
Verified step by step guidance1
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.
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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.
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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.
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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.
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