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The accepted mechanism for the following transformation involves a carbocation rearrangement. HBr -Br Rather than occurring via a methyl shift or a hydride shift, a carbon atom of the ring migrates, thereby converting a secondary carbocation into a more stable tertiary carbocation. Using this information, fill out the blanks for intermediates choosing from the structures below. Ignore stereochemistry. [ Select ) [ Select ] Br A В E +) F G

The accepted mechanism for the following transformation involves a carbocation rearrangement. HBr -Br Rather than occurring via a methyl shift or a hydride shift, a carbon atom of the ring migrates, thereby converting a secondary carbocation into a more stable tertiary carbocation. Using this information, fill out the blanks for intermediates choosing from the structures below. Ignore stereochemistry. [ Select ) [ Select ] Br A В E +) F G

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Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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The accepted mechanism for the following transformation involves a carbocation rearrangement. ![chemical reaction] The reaction depicted starts with a cyclopentene and hydrogen bromide (HBr). The end product is a cyclopentane with a bromine atom. Rather than occurring via a methyl shift or a hydride shift, a carbon atom of the ring migrates, thereby converting a secondary carbocation into a more stable tertiary carbocation. Using this information, fill out the blanks for intermediates choosing from the structures below. Ignore stereochemistry. [Diagram of process] 1. Start with cyclopentene 2. First [Select] placeholder for intermediate structure 3. Second [Select] placeholder for intermediate structure 4. End product: cyclopentane with bromine Potential intermediate choices (labeled A-I): - **A:** Cyclopentane with a positive charge on the secondary carbon. - **B:** Cyclopentane with a positive charge on the primary carbon. - **C:** Cyclopentane with a positive charge on a different secondary carbon. - **D:** Cyclopentane with a positive charge on a methyl group. - **E:** Cyclopentane with a positive charge on another methyl group. - **F:** Cyclopentane with a positive charge on the tertiary carbon. - **G:** Cyclopentane with a tertiary carbon and positive charge. - **H:** Similar structure with different methyl group positioning. - **I:** Another similar structure with variations at the methyl group. These structures illustrate possible carbocations that could rearrange into more stable forms during the reaction mechanism. Your task is to identify the correct intermediates to complete the transformation.
Transcribed Image Text:The accepted mechanism for the following transformation involves a carbocation rearrangement. ![chemical reaction] The reaction depicted starts with a cyclopentene and hydrogen bromide (HBr). The end product is a cyclopentane with a bromine atom. Rather than occurring via a methyl shift or a hydride shift, a carbon atom of the ring migrates, thereby converting a secondary carbocation into a more stable tertiary carbocation. Using this information, fill out the blanks for intermediates choosing from the structures below. Ignore stereochemistry. [Diagram of process] 1. Start with cyclopentene 2. First [Select] placeholder for intermediate structure 3. Second [Select] placeholder for intermediate structure 4. End product: cyclopentane with bromine Potential intermediate choices (labeled A-I): - **A:** Cyclopentane with a positive charge on the secondary carbon. - **B:** Cyclopentane with a positive charge on the primary carbon. - **C:** Cyclopentane with a positive charge on a different secondary carbon. - **D:** Cyclopentane with a positive charge on a methyl group. - **E:** Cyclopentane with a positive charge on another methyl group. - **F:** Cyclopentane with a positive charge on the tertiary carbon. - **G:** Cyclopentane with a tertiary carbon and positive charge. - **H:** Similar structure with different methyl group positioning. - **I:** Another similar structure with variations at the methyl group. These structures illustrate possible carbocations that could rearrange into more stable forms during the reaction mechanism. Your task is to identify the correct intermediates to complete the transformation.
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