Textbook Question
Make models of the following compounds, and predict the products formed when they react with the strong bases shown.
(d)
8. Elimination Reactions
SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)
3:18 minutesProblem 63d
Textbook Question
Silver-assisted solvolysis of bromomethylcyclopentane in methanol gives a complex product mixture of the following five compounds. Propose mechanisms to account for these products.
(d) 
Verified step by step guidance1
Step 1: Recognize the reaction conditions. The presence of AgNO₃ and CH₃OH under heat suggests a silver-assisted solvolysis reaction. Silver ions (Ag⁺) can facilitate the departure of the bromide ion (Br⁻) from bromomethylcyclopentane, forming a carbocation intermediate.
Step 2: Identify the carbocation intermediate. The loss of Br⁻ from bromomethylcyclopentane generates a cyclopentylmethyl carbocation. This carbocation is relatively stable due to hyperconjugation and inductive effects.
Step 3: Consider possible rearrangements. The cyclopentylmethyl carbocation can undergo a hydride shift or ring expansion to form a more stable carbocation, such as a cyclohexyl carbocation. This rearrangement is driven by the stability of the six-membered ring structure.
Step 4: Analyze nucleophilic attack by methanol (CH₃OH). Methanol can act as a nucleophile and attack the carbocation, leading to the formation of methoxy-substituted products. Additionally, elimination reactions can occur, forming alkenes such as cyclohexene.
Step 5: Account for the product mixture. The reaction can yield a variety of products, including methoxycyclopentane, methoxycyclohexane, cyclohexene, and other rearranged or substituted compounds. Each product arises from different pathways involving carbocation rearrangements, nucleophilic substitution, and elimination.
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3mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Silver-Assisted Solvolysis
Silver-assisted solvolysis involves the use of silver salts, such as AgNO3, to facilitate the nucleophilic substitution of a leaving group (like bromine) in an organic compound. In this reaction, the silver ion helps to stabilize the leaving group, promoting the formation of a carbocation intermediate, which can then react with the solvent (methanol) to form various products.
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Nucleophilic Substitution Mechanisms
Nucleophilic substitution mechanisms, primarily SN1 and SN2, describe how nucleophiles attack electrophiles to replace a leaving group. In SN1 reactions, a carbocation is formed as an intermediate, allowing for rearrangements and the possibility of multiple products. In contrast, SN2 reactions involve a direct attack by the nucleophile, leading to a single product without intermediates.
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Product Mixture and Rearrangements
The formation of a complex product mixture in reactions like the one described can result from various pathways, including rearrangements of carbocations. When a carbocation is formed, it may undergo shifts to more stable forms, leading to different structural isomers. This complexity is particularly evident in cyclic compounds, where ring strain and stability can influence the final product distribution.
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